The Viall Files - E533 Ask Nick Updates Special Episode - Part 4

Episode Date: January 27, 2023

Welcome back to The Viall Files! Today we have another special “where are they now” update show where we give you updates from our past callers, to see what’s happened in their situations and relationships since appearing on the show. We bring on our first caller who had a tumultuous relationship with her birth mother and wasn’t sure if it was better to forgive her and try to establish peace, or if she should move on and prioritize less toxic relationships. Our second caller had gone to a Harry Styles concert with a platonic guy friend from her apartment building, only to have things turn romantic. Has she listened to Nick’s advice and addressed the shift in dynamic head-on? Finally, we get an update from our caller that was thinking about hooking up with her boss’s - despite him showing some fuckboy qualities. Whose number did she get at the family holiday party, and who booty called her while with her boss? We also have some written updates! Our caller who was debating moving out from her boyfriend despite being financially dependent, the texting office hours question of if a guy who ended things might want to pursue her in the future, and our caller who needed to break up with her ex - again - all write back in to let us know exactly what happened.  To catch up on all of these callers original questions please see the show numbers:   Original Episode numbers for callers: Episode Number: #489 Ask Nick - He Loved Me Until He Knew My Secret Episode Number: #510 Ask Nick - Is Harry Styles Our Matchmaker? Episode Number: #516 Ask Nick - I Want a Tattoo to Memorialize My Ex  Original Episode numbers for written updates: Episode Number: #507 Ask Nick - Bad Sex, Good Connection Episode Number: #438 Going Deeper w/ Hannah Berner - Male Engagement Rings & 3rd Wheels  Episode Number #510 Ask Nick - Is Harry Styles Our Matchmaker? “It’s not about being right, it’s about being happy.”  If you are interested in running a book club in your city, send an email to: [e-mail]  Please make sure to subscribe so you don’t miss an episode and as always send in your relationship questions to [e-mail] be a part of our Monday episodes.  To Order Nick’s Book Go To: http://www.viallfiles.com Support a Local Bookstore: https://bookshop.org/books/don-t-text-your-ex-happy-birthday-and-other-advice-on-love-sex-and-dating-9798212185622/9781419755491 To advertise on the show, contact [e-mail] or visit https://www.advertisecast.com/TheViallFiles Episode Socials: @viallfiles @nickviall @alison.vandam @liffordthebigreddog

what's going on everybody welcome back to another exciting episode of the vile files the update special for january thanks for joining us i know you all love these episodes and we love bringing it to you ali amanda how are you i'm just used to ali being there yeah i it seems like it was an incredibly unpopular decision are you still reading the youtube comments i yes because i value what people have to say a lot of the time it's like oh great you're gonna make it worse now no but this is like i do think there's obviously an element of discernment where it's like you have to be able to like i understand that like it can be very detrimental to have like criticism in one's ear but i think it's like

valuable to hear what people are responding to and to like adapt based on it this is like when my sister grew up and she hated diet coke and she just made herself keep drinking it until she could tolerate it and then she finally liked it that feels like it's giving the same energy to amanda reading no it'd be like if but how do you drink diet coke and one in four times it made her vomit and then she kept drinking it and then it just made her burp really badly yeah but like so that's what i'm saying like how you're just trying to, so you think the benefits of the constructive feedback outweigh the emotional impact

of the negative unnecessary critical comments. Yeah, because I think I also, and we were talking about this right before about like eyeliner stuff. And so I feel like this is related. So I'm ready for this connection. So I just think I was tremendously, for a really long time, had tremendous insecurities about physical stuff and the way I was perceived.

And so I think there is something really reclamatory and liberating about being like, I don't care that this woman thinks my hair was done in a gas station bathroom. That's a creative thing to say. It's an interesting, yeah, I mean, listen, if you can get to that point of desensitizing yourself, I guess I always wonder, and I certainly have read stuff and I've read stuff going in with the idea

of feeling like I had the self-awareness to compartmentalize. Compartmentalize. Thank you. Certain types of feedback. But I don't know if we really fully know. But we're in two different ballgates. Like I'm sure like Bachelor Nation feedback terrifies me. Like I feel like I don't think this is something where I'm like,

everybody should read the comments. I think I'm in a very special beautiful cocoon niche where there's like there's not too many about me it's all from people who are like dedicated listeners who like for the most part are like actually listening to this show and like it's i think they're really thoughtful and so for me it's like if someone's gonna say something to me like or if they're gonna write something like i want to listen to them i mean maybe they're wonderful i i i truly amanda does have a lot of fans there's a lot of amanda stands for sure there's alley fans too you know but like i just like amanda has some very specific effervescent comments do you queen i'm just saying she has

some good fans okay yeah sometimes i screenshot them and put them in a little folder called don't give up. Okay, wait, but the reason I was going to talk about eyeliner was because there was a period of time where I felt so uncomfortable going anywhere without makeup. It felt very, very obligatory. And then ironically, moving to LA was kind of where I was like, I don't give a fuck anymore. Okay, people know what my face looks like. Oops. But I feel like I I don't give a fuck anymore. Like, okay, people know what my face looks like, oops. But I feel like I had so many different eras, like in a fun way.

And I still love wearing like, and to be clear, everyone should wear makeup when they wanna wear makeup. I think it is so valid. I was for a while wearing it from like, I need to cover this shit up because it is horrific standpoint. But it was kind of fun. It's looking back at photos and being like,

oh my God, all my different eras of eyeliner. Do you have any wild makeup photos? You have any like jump scare makeup photos? There was a photo of me moving into my freshman dorm room and I had like a full contour on and it was a bit aggressive, which no one told me, but my mom posted on Facebook,

like this is Allie's dorm and this is whatever and there was a photo of me from the side that she made black and white just out of nowhere and I have a feeling that that's why and it somehow just made it look better if it was not in color yeah it's just like cheekbones cheekbones you put them black and white easy peas poppin yeah yeah so you're doing a new yes you're in a new era tell us about it all right everybody gather around i'm starting a new potential era i don't know we're only a few days in but for the longest time i've been doing like a black winged liner

that's just kind of been like my signature thing sleek powerful like on the lot on the eyes there was some liner coming like it goes up and then it comes back down. Okay. Like a wing. Do you mean like cat eye? I feel like I know what you're talking about. Yeah. I've been repping that for a while. And can I just say, it is hard to get the angle right.

Do we have any photos of this? I mean, I can't picture it. Literally the way she showed up to work every single day. Except for this week. But when I got glam for your engagement party she didn't do that and she did more of like a softer liner and i was very into it so i was like i'm gonna try and do it myself so here we are you look very nice it looks great do you like it feels like maybe you're blending it slightly i am just using a brown eyeshadow with a straight brush and just yeah like i'm not

it's not even a liner, it's powder. Are you open to feedback on if that's correct? From you? No. But we're talking about like feedback. Oh,

absolutely. I love you as a man. Leave it down in the comments below how ugly I am. Are you open to feedback on your physical appearance and makeup? I truly have no input on this.

I know how that sounded. Yeah. Let me give you some notes. The man who's like, what's a winged liner? The best part is that you asked, I feel like the person who has the self notes the man who's like what's a winged liner the best part is that you asked i feel like the person who has the self-awareness who to like who doesn't have a self-awareness to like give feedback on some of their employees makeup also does not have the

self-awareness to be like are you open to feedback which is so funny about it i have absolutely no i'm saying from the audience sure i mean it's kind of a hard angle to see it, but absolutely. Well, just maybe like- And if you say something mean, I'm going to read it and I'm going to get mad at you. No, I don't mean necessarily like critiquing like your face or the job that you do. You look wonderful,

but like you just described how you go about doing this. And even for the people listening, they might say, well, you know, like try this. Yeah. Try like a- Give me your hacks. I'll keep trying. I love a good life hack. A certain type of like, you know, like, try this. Yeah. Try like a. Give me your hacks. I'll keep trying.

I love a good life hack. A certain type of, like, you know, maybe there's a stroke. Yeah. Like from an angle of a. Like an aha moment of eyeliner when you were like, oh, this is good. Like, please share. Yeah. Always looking. Hey, I've slept with leggings on my head many a time.

So I'm very open to anything new that might change my life. Hold on to your kilts, dearies. Peacock original The Traitors is back with a new season of strategy, betrayal, sabotage, and murder. This killer season features an all-new celebrity cast that Vulture hailed as reality royalty, living in a Scottish castle for the ultimate murder mystery competition.

We're talking fierce competitors, reality stars, and public figures battling it out for a whopping cash prize. This season's cutthroat missions are next level, just like whatever Alan Cumming pulls out of his brilliantly eccentric wardrobe. One thing is for sure, these 21 players will do anything to avoid a plot in Alan's graveyard. Find out why critics and audiences alike are raving about the Emmy award-winning series. The New York Times is calling it a murder mystery with clothes to die for, and Vox adding that it should be your new reality TV obsession.

We are certainly obsessed. Stream every episode of Traders Now only on Peacock. Ladies and gentlemen. What are you doing? What do you mean? Just keep it simple. I'm making the promo. Just keep it simple.

Just say, hey, we're the Brav Bros. Two guys that talk about Bravo. Ladies and gentlemen, boys and girls, we're the Brav Bros. No. Oh. Dude, stop with the voice. Just keep it simple. I've seen promos on TV, dude.

This is how you get the fans engaged. This is how you get listeners. We're trying to get listeners here. If we just say, oh, we're two dudes that talk about Bravo, people are going to get tired of it already. We need some oomph. All right, then fine. Let's try to do it with your voice.

Bravo, bros. Good job. Derek, our producer, said we should, like, do, like, a, kind of an update on, on our goals of the new year,

like a, like a... All I can think about is you describing Derek as there's a man in the room there's a man in the room named derrick that was like a beloved center of our team but yeah i mean i think it's our goal of this show as you guys know to continue to engage with you guys and we always wanted to build a community uh We like to think of our show as a place that people can either go to feel less alone about their own relationship or interpersonal struggles,

whether you're dating or in a relationship or whether you're just kind of single or just a place to go to listen to other people's stories and feel less alone and just have some fun. And so all jokes aside, I mean, I think we, well, I don't read YouTube comments, but especially when it comes to this show, Ask Nick, we definitely invite you guys to have discourse around the stories and even our advice or comments. As long as you guys keep it respectful and productive, more just like conversational, you know, certainly with us and more importantly with one another, you know, whether it's the Vilefiles IG or Instagram or our TikToks, we always post a lot of clips from

the Ask Nick's or certainly on the YouTube channel. We like to see these types of conversation and every once in a while we might, as we did a couple of weeks ago, respond or, you know, it might add to the conversations. It might give us a thought that we didn't think about. So we definitely want to keep, you know, interacting with y'all and engaging with you all and having conversations. So we encourage you guys to do that on our platforms. Just, you know, keep it nice and productive. Because it's nice to have people to talk with about this type of stuff. And I guess we want to have our own water cooler talk

as it relates to our show with one another, with each other, with you guys. So hopefully we can do that. Anything we want to add to that? Did that sound great? I love State of the Union. We do this every update episode. we can we can do that anything we want to add to that did that sound sound great i i loved state of the union can we do this like every update episode what do you love about it oh oh it gets boring oh the gravitas like i just feel like it's like so fun to be like yeah we talk a lot about

like dicks and situationships and we're giving you a state of the union on it. Like, I just find that marvelous. Do we talk a lot about dicks? Yeah. Do we? How frequently do we talk about dicks? Yeah. Okay, well, y'all talk about dicks. Should we talk more about dicks? As the person who's currently reading the Ask Nick email, y'all talk about dicks.

Okay. Okay. All right, we believe you. Maybe, do we need more dick conversations? I don't know. No, I think. We talk enough about it. I think we talk enough about dicks. I was mostly saying that as an example

of some of the sillier things we talk about. I think we talk a lot about emotional intimacy and boundary setting, but that's not as fun as then talking about dicks. I find like dicks are gross. Do you find like dicks are gross? I don't find that you're alone in that thought. The look on my face that's

been on my face for the last 30 seconds has nothing to do with you it's just me thinking about penises i well so okay so the thing is is like do i think a dick is inherently aesthetically pleasing absolutely not but i do i do try to be mindful about being aware of some of the double standards and in terms of like as we are moving towards a more like equitable and compassionate society that is still existing within the gender binary like being like where are some of the areas where like this would not fly if it was reverse and is there good reason for that or do we need to change it and i think like giving the penis more aesthetic love you think not aesthetic love but just like not shaming it because i shouldn't be shaming penises i'm not telling

you not to do anything did you know do penises i don't know i certainly can't speak for all men but i don't know if men are sensitive to the penis not getting like like some aesthetic love. I was listening to a podcast episode recently about penis crimes and they were going into like the background of penises and like genetically, like evolution wise, whatever. It was wild.

Like the dome part of the penis, it's basically like has a function. No, it literally has a function. When you say the dome. To scoop out other people's sperm that might be in someone's vagina in order for like you to be the survival of the fittest like there's like it's crazy there's like an evolutionary type of in order for like you to be the one to procreate i mean maybe who where did you get this information it's like i saw in some random podcast yeah and how did we verify that i trust this podcast okay

i guess i fall asleep to it every night so we don't know if that's true so we have not we don't but i believe ali it's possible but can we talk we as a society we just go evolution and we skip over the fact that we had this insane transitional period as human beings we're like like we're just like monkey to person and it's like there were so many generations and iterations of human beings with various varying degrees of functionality penises the other thing like my boyfriend met because he's a big space guy so i think kind of inherently like creation of the world thoughts it's like it's the kind of science where it's like i think we all just like put it in a little box and are like we're just

not going to think about that like we would be we would not be a functional society if we just kept thinking about how space is infinitely expansive like we wouldn't it's insane to think about i think we don't even think about how like the world works with itself i guess you know i don't i think nowadays we're we're only thinking about the world that with itself, I guess. You know, I don't, I think nowadays we're, we're only thinking about the world that relates to like our own individual problems or then our, you know, our community. On some level, I think for the most part,

that makes the most sense. You know, I don't think we should necessarily lose ourselves in worrying about like, we have a bit of a doomsday kind of mentality with all the news out there and of like, oh, what's the point? You know, it's all going to go to shit, you know, which I don't think is very healthy, but I think, yeah, I don't know. I think there's a lot of productive information out there that I guess, and some levels can make you like ease your mind on, on the state of the world,

which, because nowadays it can seem rather grim, but like history, you know, there's been grimmer moments in our history. I don't know what I'm trying to say. No, I think there's some tidbits in there. I have, can I just say very like quickly, I have such a specific anxiety. Like, do you know, like, I feel like there should be a word for like dayreams that are not a fantasy, but anxieties,

like little day nightmares or day night sweats. Do you know what I mean when you just end up down a very involved anxiety rabbit hole in your brain? One of the ones I go on a lot is being like, there is going to be an apocalypse situation i'm going to somehow have like one cracked screen iphone and i'm and like maybe a charger but like electricity is going to be gone and i because i don't understand the science of it i'll never be able to recreate it and like it's not even i guess like it's not that the iphone would need to be functional but it's just like this specific thing of like oh my god like i won't be able to explain electricity because i didn't i didn't retain that from science class like even though someone has invented someone has invented electricity i feel like wait it's the end of the

world yeah it's like apocalyptic societies crashed and maybe they're zombies but like it's you know rubble everywhere 10 of the human species is left and it's survival of the fittest we're hunting for food and you're worried about being able to explain electricity to to then re-harness it into the next generation of people who yeah how are you the only one left why are you the only one left you know anxieties are so realistic and take into account all the factors of life i'm just like that that worries you to the point where you have anxiety because i feel guilty that i don't know how like the world works more well do you want to like print out like a wiki how and just have like a binder do you want to in google do you guys understand electricity to the point where you could like.

No, but I don't intend to have to. Do I understand electricity? I don't think if the world went down, I'd be the only one left. There's no way. Yeah, I'd be like,

I would be like, hey man, there's this thing called electricity. It's enlightening. There was this guy named Benjamin Franklin that flew a kite. Franklin. A guy named Benjamin Franklin

that flew a kite at some point. And smarter people than me will be like, yeah let's let's figure that out but i do know that it exists and i suppose on some level i can explain it to a person who can run some appropriate experiments i think it's just the idea of like i'm dependent on systems that i don't understand and there is the infrastructure to understand the systems and i do not utilize it because i got other stuff i want to be doing and i think i feel like unsure of that choice it's an interesting thing to worry about it's ridiculous it's absolutely preposterous and it's never going to happen and that's the state of the union is i'm worrying about if I could explain electricity to the next generation of humans. I mean, I worry about, I guess, dying and before I can be a dad.

That's the only like life goal that I've always had that I haven't yet to accomplish. And so like I'd like to be able to do that. And maybe that makes it me selfish that I really don't care once I'm gone if people lose the ability to have electricity. I mean, I hope y'all figure it out. I really, I do. He's like, good luck, kids. Here's what I think about all this stuff. And this is what, when we, again, worry about the world, and I think it's easy. And I think think i wonder if this is something that might be more prevalent with gen z it could be wrong i don't know i think everyone experiences through a certain level but like because of social media and the news and and the way we put stuff out there i

think it's easy to get anxiety and and feel kind of this crippling amount of of fear and and and kind of being told like what's the the point? There's no hope for anything or anyone, you know, and I don't think that's the way to change anything. I think for me, it's keep your house clean, so to speak. Do my part, you know, I try to do my part for myself and my family and then whatever I've left extra, and I hope that I'm able to have extra at certain points, I try to be good to strangers around me. And I try to be a part of my community. And I try to do my part within reason. And that's as much as I can control. I do try to practice the advice that I often give to people, which is very much control what you can control.

And that certainly helps my anxiety in general because it makes me feel a bit more powerful and I can manage expectations. And so I just try to do my part. And I'm hoping that other people are doing the same. And if we do that and we're willing to put in the work, I think this world has a chance to keep going and keep thriving. And we've had darker days in the past. And I think we're scrappy. Humans are scrappy. Yeah. And innovation is born out of sheer necessity and the instinct to survive.

I think where I might ever so slightly hold a different opinion is that I think it is necessary to get riled up to show the gravity and like the scale to which we need innovation, especially with like climate stuff. Sure, to a certain extent. Sure. Yeah. But like you have to make sure that we're willing to do the innovation and put in the work. Yeah. And that it's not just like being crippled by the magnitude of the problem. And echoing this kind of message of like, what's the point?

Hold on to your kilts, dearies. Peacock original The Traitors is back with a new season of strategy, betrayal, sabotage, and murder. This killer season features an all-new celebrity cast that Vulture hailed as reality royalty, living in a Scottish castle for the ultimate murder mystery competition. We're talking fierce competitors, reality stars, and public figures battling it out for a whopping cash prize. This season's cutthroat missions are next level, just like whatever Alan Cumming pulls out of his brilliantly eccentric wardrobe.

One thing is for sure, these 21 players will do anything to avoid a plot in Alan's graveyard. Find out why critics and audiences alike are raving about the Emmy award-winning series. The New York Times is calling it a murder mystery with clothes to die for, and Vox adding that it should be your new reality TV obsession. We are certainly obsessed. Stream every episode of Traders Now only on Peacock. Ladies and gentlemen. What are you doing?

What do you mean? I'm making it. Just keep it simple. I What do you mean? Just keep it simple. I'm making the promo. Just keep it simple. Just say, hey, we're the Brav Bros. Two guys that talk about Bravo. Ladies and gentlemen, boys and girls, we're the Brav Bros. No.

Oh. Dude, stop with the voice. Just keep it simple. I've seen promos on TV, dude. This is how you get the fans engaged. This is how you get listeners. We're trying to get listeners here. If we just say, oh, we're two dudes that talk about Bravo,

people are going to get tired of it already. We need some oomph. All right, then fine. Let's try to do it with your voice. Bravo, bros. Good job. All right, well, we have a great episode for you. We have some great updates.

Make sure to email us at asknickatthevilefiles.com for all your updates or just your questions uh don't forget um our amp show is every thursday i know yesterday uh we moved it up a couple hours because of some scheduling conflicts that i had but going forward it'll be 6 p.m pacific 9 p.m eastern my parents fully enjoyed it i had so many people in that waiting room in the little chat it was great this is for silliness this is for in the moment joy and conversations and talk a lot about like yeah like just all specific around dating uh talking about various ics and we debate a lot of like oh we just we debate a lot of like simple dating

conversations it's fun it's fast paced is this a red flag or am i being too picky like that kind of stuff we have people call in for very specific questions so i mean ask nick i think is more of like a long form this is more of a quippy fun so it's every thursday uh 9 p.m eastern 6 p.m. Pacific. Get your drinks. Get it. And eventually, I think, we'll start doing more updates. And I know a lot of people have asked about Better Date to Never being played somewhere else for the people who can't check it out live. We love our Canadian listeners. Eventually, we will find a place for it.

We're working on some premium stuff. And so, yeah. We're obviously trying to put out a lot of stuff for you guys and we're trying to find the right places for it. So, throw out ideas, obviously. Let us know what you guys are excited to hear

and listen to. We always love some constructive feedback. And help us grow. So that way we can continue to put out more content. A great way to do that would be to give us a little five-star review. Yeah. That's always great.

Also, we are so thankful for anyone who, when you guys share on your socials and tag the show, honestly, that's the best. That's the thing we appreciate the most, of you guys spreading the word about our show and tagging us. I try to share as many as possible. I can't get to them all, but I appreciate when you guys do that.

And it's really important for the show. So we thank you for doing that. Anything else we have to get to? Next week, we have Jim Jeffries coming in for a Bachelor recap. And we have the Lautners. The Lautners, Taylor and Taylor. Taylor and Taylor. That should be a ton of fun. And also, if you're submitting to Ask Nick, in for a bachelor recap and we have the lotners the lotners taylor and taylor taylor and taylor

that should be a ton of fun and also if you're submitting to ask nick whether it's amp texting office hours or just your your classic ask nick please uh if you can make the subject line as attention grabbing as possible that is so helpful if you give us a little like taste taste of what's to come we get so many submissions uh and we definitely want to be continually getting on some of the most like relatable exciting interesting stories and so give us some of the goods in the subject line the tailors are married now right yeah yeah they gave me some like some marriage advice yeah some wedding planning or marriage i'm full on like engagement mode i love it uh well thanks for listening as always guys uh anything else let's uh let's get to our updates let's ask nick your sexy questions welcome back michelle

how are you i'm good how are you thanks for having me again yeah welcome back Good to have you. So you called in, what episode was it, Amanda? 489, I think. Yeah, it was 489. 489. First caller. Yeah, first caller of the episode. And you were adopted. Yes. And you reconnected with your birth mom. And were you getting married?

mom and and were you getting married so we we had a fight around my wedding because she wasn't invited okay and then we stopped talking for years and then she emailed me letting me know she was dying of cancer yeah let's play a quick clip from that episode to bring our audience up to speed for those people who might have forgotten or haven't listened to it? I am adopted and I have a long standing relationship with my birth mother that has been sometimes not so easy. Do I move on from the past and continue a relationship or do I not move on, or do I like not move on, move on in a way, but not continue with her. When I was about 16 years old, she had contacted me privately on Facebook and said like, you know, she wanted a relationship and not to tell my parents. Then we had this like secret relationship for like two years almost. But like, there was like two years almost.

But like there was like little things that she kind of would say and do that were really bizarre to me. She'd be like, I cry when you don't wish me a happy Mother's Day. And like, I don't know, it's just so, so bizarre. And I was like, well, you know, like you gave me life. I'm thankful for you, but you didn't raise me, me and my mom, my adoptive mother, we've had a hard relationship, but like as adults, we're so close now. And like, that was the first time I really felt like I could stand up for my mom. We didn't talk for years. She just emailed me last April telling me that she has cancer and that she's dying and that she was given like six months to live. And she just kind of was like, hey, I thought I should let you know.

And if you wanted to have a relationship, like, let me know. So she did put the ball in my cart. It wasn't forced. Not to sound, uh, we believe her for sure. I don't, I mean, I don't, or is there a part of you that even wonders? Part of, well, part of me, I'm sure she's maybe sick, but like, there's just been some kind of like sus things that's happened since she told me. And there's just like things that she's told me throughout my life that make no sense to me, like about my birth dad so i have to admit yes it is really hard for me to 100 believe her yeah listen and this is really about expectations and boundaries not to sound like a brokered record um and like i don't fault you at all because obviously your mom you know she that there's a reason why you're not supposed to reach out to, to minors, uh,

in this type of situation for the confusion and emotional, like, um, potentially emotional, emotional kind of triggering or scar that you could put a, a minor in and dealing with this type of, how could you possibly expect someone like yourself in that situation to do what's best? And it's, I can only imagine it can be very confusing at any stage in your life, let alone being 16, 17, whatever. But it sounds to me like the challenge, do what you think is right. At the end of the day, this is a situation that I believe that like, you just have to truly decide what's best for your mental health and the people around you and your wellbeing. And that's what's most important. Um, as long as you can still try to still be empathetic to the people around you. Um, but if you have a relationship, if you choose to have a relationship with your mom, you're still going to have to set expectations and boundaries,

right? And most importantly, it sounds like you just say you reach out and say, you know, if you feel this way, some version of, I would love to have a relationship with you. Please don't give up. Fight. You know, encourage or give her, you know, obviously the empathy and sympathy. And then, like, regardless of her diagnosis, like, challenge her to fight for herself. But if she does want a relationship with you, it's still, like, what she seems to be struggling with is she wants a relationship with you on her terms. Definitely. And, and a relationship of any kind only works when it's on

mutual terms of, of both people. When you are willing to hear someone else, it's like, all right, well, what, how, how do you want this relationship? Let me explain to you how I want this relationship. Let's listen to each other, set expectations and see if there's a fit there. So remind me the advice I gave you. So you pretty much said, you know, like, it sounds like she's the kind of person who's not going to give you, you know, the story that you need. And with the limited time that we assumed I didn't have with her that it would be good to set a healthy boundary about not involving anyone else in our relationship

and just kind of having the two of us moving on enjoying what's left I think I mourned the relationship so many times throughout my life that it it wasn't as hard as i thought it would be i'm just glad she's not in pain anymore because i did get to say my goodbyes and two days before she passed after after you got on a call with us i guess i'm curious what what specifically did you do okay so literally the exact same day as the call like i think we finished at like 10 at like 11 o'clock I messaged her and I just said like hey how are you I'm okay how are you I said I'm doing all right I'm sorry I didn't reply sooner I just needed some time to figure out my feelings and figure out what I wanted to say I said I want a relationship with you and I want to leave the past in the past I think it will be best if we

don't bring other people into our relationship like my mom and we focus on you and i i just want to make the best of what we have left together great so then she replied later that night she said well said my dear before i read this we need to remember in the first episode how she said some pretty nasty things about my mother yeah this well said my dear i agree we move forward just know that it was never my intention to hurt you or offend you you don't know me well enough to know in that email if i say something it's said with best intentions in person you would see the humor on my face two big lessons i've learned in life to assume the best of others and to not take offense and i said looking forward to seeing you soon let Let's plan another

video call with me. We can. Okay. Yeah. So kind of left it at that. I was like, okay, cool. I felt really good, like weight off my shoulders. I felt really good about the advice you gave me. And like, I also set a boundary with my mom, like my adoptive mom telling her that like, unless I approach her with information about my birth mom, I don't really want to talk about it because it just seemed to, I just didn't want to talk about it because it just seemed to, I just didn't want to intertwine the feelings. Totally. Yeah.

Yeah. So that was good. She respected that. So that was the same day we filmed, which was September 27th. And then she kept putting off like video chatting because she ended up being admitted to the hospital. Old time.

She was a kidney failure and she wouldn't video chat. And I was like, okay, whatever. And then I think it was on like the 12th of November, I just had this gut feeling that something was like really wrong. So I called the hospital. And because I wasn't like on the list, they couldn't give me any information. But they said they'd have someone call me back. And I woke up the next morning from my birth mom's cousin so I guess technically my cousin saying like you need to go say your goodbyes she's not doing well so I like literally got up got

dressed went to the hospital and she was like um dated and all that like couldn't talk and I met her niece and her best friend which is nice to have that connection now um but I said my goodbyes I sat with her you know I I was in a very good spot with us and I'm really glad I was in that moment because that's the last thing I wanted to was like be upset and say things I would regret you know yeah I said my goodbyes and then she ended up passing away on the 15th like two days later so super sad um but again like she's no longer in pain she was suffering for a while so I'm glad she's not suffering anymore but then like a lot of stuff came out after the passing which is the wild stuff wild like what so i ended up connecting with the niece and i was like hey do you mind like adding me on her facebook if you have her password i'd love to like be able to look

back at the photos when i you know because i don't really have a lot of things um and she said oh i don't have a password but i'll send you screenshots screenshot of an entire photo album of pictures of me and my child and my husband that I never sent her I keep my son very private off the internet for various reasons but I was like hey that's kind of weird she had pictures of me pregnant her and I didn't speak until my son was like two so she was stealing them off my Instagram or had like a fake name or something and I was like are they public photos though I think she might have like she blocked me on social media and then she might have unblocked me and been able to see my private account I can't remember if I had her block but when Grayson was first born, my son, I did share photos of him online because at that point I wasn't like concerned.

And so she was, yeah, I guess screenshotting and then uploading to her Facebook. How does that make you feel? Not good. Why? Well, I just feel like, you know, you weren't talking to me and you were really mean to me. And then all of a sudden you think it's okay. Sure. The caption of her album was like my grandson, daughter well why does that upset you i don't know i think it's just because she

thinks she was like really entitled to like have this i don't know if it was a matter of entitlement i think it was more uh it's still her grandson certainly by blood whether you guys had a relationship or not and again it's just this is just a by blood, whether you guys had a relationship or not. And again, it's just, this is just a matter of perspective, you know, you can choose to look at it a couple of different ways. Like you can be offended, like you're right. Like you could, you can take the, like, also just don't forget like the work that you put in, um, prior to your mom's passing to get to a place of, you know, more love than frustration, you know, or more understanding than criticism. And, you know, it's not about necessarily being

right. It's about, you know, being happy and just trying to getting to a place where you can just have some kind of positive thoughts about your relationship with your mom right so at this point now that your mom has passed you're in full control of how you perceive that relationship right yeah yeah and i kind of like did move on from like move forward from all the photo thing because i i asked her cousin if she was able to like delete the pictures of my child at least and she said no problem because she was able to get on her her facebook but it was like what shook me for like a couple days to like get over now I'm like I'm doing the work like move past this was like she made a post like literally after we set boundaries about how like my students literally were use the

words that we're in touch and i don't really get to be a part of their life because her mother the woman i chose to give my baby to is so jealous and insecure so that set me off obviously because i was like oh we just set this boundary and she said i don't have any bad intentions yeah i listen your, we know was an imperfect person. Yeah. Oh my. Yeah, exactly. It just doesn't feel all that productive. Like, is it that shocking that your mom, despite you having what felt like a fairly productive conversation via text was a step in the right direction? Is it all that shocking that your mom. What that route, you know what? No. Yeah. I mean like even at that route, but but like we all like we talk about boundaries all the time in the show and people are like oh yeah that sounds

great but like there's enforcing those boundaries and following through those boundaries is a whole another step and a whole another learning process and we often like are really good at first and then we you know get a little sloppy it's no different different than like, not that we're big on diets here, but like the idea of a diet, right? It's like, I want to eat healthier. And then like you're really good for a couple of days or working out or whatever it is, like incorporating change in your life.

It can be a challenge. And so I'm not sure where this is coming from on your end of, it's almost like your mom has passed and so you just have a choice you know internally to um how do you want to cement your lasting thoughts of your mom we know she was an imperfect person and let's say for example that your mom hired a private eye that was spying on you and taking pictures. Like, yeah, I get it's a little invasive and creepy. But the other way to look at it, especially now knowing that your mom has passed and like whatever certainly fears of like is a safe or can I trust her? You know, like is my biological mom well-intentioned?

Like I can understand if your mom was still in the picture and alive and there was this risk of like, is she going to keep hiring a private eye? But she is no longer with us and she has passed, right? And so you can simply choose to look at it as, well, maybe unhealthy and maybe not in a way I would have gone about it. It came from a place of love. It came from a place of my biological mother having some thought, like maybe regrets about giving you up or just struggling about not having the relationship she wanted to have, whether she was fairly judging your adopted mom or not, or you, that doesn't really matter at this point. The point is, is that your mom, it sounds like on some level loved you and wanted to be in your life and wanted what's best for you. And whether she actually showed that productively or not, or let her own selfish needs get in the way of what might be best for you,

it's kind of a moot point at this point because you're unfortunately no longer able to have or build a relationship with your mom. So now it's just more about cherishing the memory of your mom. And I think it would just do you good to try to just always give your mom the benefit of the doubt in these situations and try to look at these scenarios in a kind of glass is half full type of of mindset rather than trying to like pick apart or find the holes or critique it or yeah or kind of have a cynical kind of approach to whatever your intent your mom's intentions were i just what good does it do at this point you know and i think and i don't think you have to like take that many leaps to see the good in your mom's actions even if her

actions weren't always the healthiest or the most productive for sure and i mean i was very like hurt for like i would say like a week and i was like angry and kind of went through like i think i went through the grieving probably process of like losing her sure yeah plus all of that but like since then i'm feeling like much better about it i didn't have really any emotion towards it until like i read it again this morning and i was like it's not healthy to read that so i actually yeah it's a little upsetting and annoying but yeah it is what it is yeah yeah wild but i did i just wanted you to know that i did take your advice and i set the boundary and i did it both people both mothers and i enforced it and i still am working on that that's good yeah and again like when you try to enforce boundaries people they will push them and it doesn't mean they don't

respect you or love you or don't care about what you think but that's their own struggle of trying to be good at at that themselves and then you can decide how much patience you want to have with people and you know with family sometimes we we need to have a little bit more patience because family is probably the worst at respecting our boundaries because there's definitely a sense of entitlement when it comes to family but yeah you know we can decide how how much of a role we want family to play in our lives but um yeah i mean and have you told your adopted mother about this this revelation yeah i mean um about your mom your your your your biological mom's posts and all that yeah yep yeah i did i waited till my parents got i felt like it

was almost part of like the last part of like kind of like healing for me was just like letting my mom know what i like had found and read and my mom's like are you surprised she literally said are you surprised i'm not yeah i know but again i just and that's fine that you did i i just i think it's just a time for healing you know and i just don't know if that was part of her healing i guess i'm like i'm like you have every right to feel that is weird because it feels like she's using you for clickbait or content than she was actually valuing the relationship so i'm right there with you thank you well the one the one point that really i have to make is it would be different if he was just kind of showing the photos and was like oh you know i don't get to see them very often or i haven't met him but like she straight up told everybody that i had talked to that my parents were like holding me from seeing her her niece said i know she was very upset your parents wouldn't allow you to see

her and i said that's not the case i think that's where i got really well yeah you're protective of your mom and you don't want people thinking otherwise of her because your biological mom is spreading lies i get that yeah i mean again i think that was the hard part but yeah i just think at this point holding on to that you know oh yeah it's not gonna do anything productive that's for sure yeah i think i do have a question for advice um her celebration of life is eventually happening here yeah and for like before i found all this stuff out i was like i don't think i was like i'll maybe go and then i found this out and i was like i'm definitely not going because like people are gonna be like oh that's her daughter who she couldn't see because her mom was bad blah blah but i'm like do i go is it gonna benefit me i don't know

i i feel like i think it has a better chance of i don't know if it's gonna benefit you or not i don't know but i feel like there's a better chance once it happens you can't you can't decide to change your mind and go true you know i don't know what harm it's going to cause you yeah you know other than maybe like being involved in some like funeral drama i mean i don't like is that really going to affect you i just like i don't know i my friend was like why don't you just like stand in the back and like go when it starts leave when it ends like don't talk to anybody this way no one's like oh my god like i mean it would be nice to meet some people but i'm not really interested in that the people i wanted to meet have a relationship with i like now i do

yeah but whether you meet them or not you don't have to like have a relationship with everyone you meet it's just up to you it's just you have to decide what you want right and you just have to decide you know your mom again is no longer with us. And she, again, like she was clearly an imperfect person, you know, and it's not to make excuses for your mom, but she no longer is even capable of working on her, her, herself. Of course. Yeah. And you just have to decide for yourself, what type of lasting memory do you want do you want to you know hang on to her imperfections and ways in which she frustrated and hurt you hurt your feelings um and you'd be justified to feel that or do you just want to like decide to forgive your mom for her imperfections

and whatever caused those and again whatever struggle she might have had in her life or her childhood i don't i don't know but i would just rather have the lasting memory of your mom as complicated as it it has as it was or or it could be is it just be generally positive and knowing that at the end of the day, as imperfect as it was, and as unhealthy as it was at time, it came from a place of love. And maybe she's in a better place to love you from afar in a way that she Because I just don't want you hanging on to this and kind of internalizing, you know, this and this relationship and keeping it with you. And just, you know, like letting it go, you know, whatever frustrations you have and just kind of forgiving your mom, knowing that, you know. and just kind of forgiving your mom, knowing that, you know, and you can decide that if my mom knew better, maybe if she was dealt a different deck of cards in life,

maybe she would have handled these situations better. And just choosing to like offer her grace in that department. Again, it's up to you. I'm not here to tell you what to do, but I just, it feels like you're open to that. It sounds like that's your ultimate goal yeah for sure understand that your adopted mom

is always, she has a right to be hurt by what your biological mom said and she has a right to be protective but I don't want your adopted mom to also even have an issue with you wanting to cherish the memory of your biological mom, I get

why she's territorial, but I just, you know, like, I just want you to be at peace with what happened and I want you to be able to move forward with a general smile. And I want you to be able to, if you, if you want to like, you know, frame a picture of your biological mother and, and, you know, have it in a special place where you can just, you know, maybe you can have a relationship with your biological mother in a way you couldn't have while she was with us. You know, maybe she's someone you just like talk to in the car or whatever. I don't know. Like that's the beautiful part of maybe death and thinking about life after death, you know, like, and again, I don't know where you, like what belief system you subscribe to, but I think there just are healthier ways of processing

this rather than continuing to be frustrated about how things she did or didn't do while here on this earth, especially when she's no longer with us. Because, yeah, it sounds like your mom went through a lot. And I'm sorry she hurt you in ways that she did. But I'm guessing if she could see it differently she would have been different 100 yeah for sure okay well thank you thank you it was nice to see you again sending you a lot of love thanks guys congrats on being the better person and just like taking the high road yeah yeah it feels hard because it's hard. It's really, really hard.

And you're doing it. And good job. It's so hard. Awesome. Well, I'm excited for the new episodes. And congrats on the new studio. Thanks so much. Thank you.

Have a great day, guys. Take care. Bye. Bye. We have a written update from our caller Madison, originally appearing in episode 507. She called in discussing the prospect of breaking up with a boyfriend who she was currently living with and sort of financially dependent on, and she didn't know how to go about navigating this situation. I'm Madison. I'm 25, and I'm considering breaking up with my boyfriend and moving out.

But one, I don't know if that's the right thing to do. And two, I'm also a little financially dependent on him. And I don't know how much that's weighing into my decision making. Okay. Well, let's start with why you are considering breaking up with your boyfriend. So we've been having just a few issues over the past, I would say two months. We've been fighting quite heavily. I mean, long story short, he's kind of thinking, he's like, okay, we either shit or get off the pot at this point. So that has just led into a bunch of other little fights. And I don't feel like I'm being loved to how I deserve to be loved, if that makes sense. I feel as though I'm the one doing a lot of the pursuing to him right now and trying to make sure he's happy,

where in turn, he knows what I need. And I don't think he's really giving me any of that. Have you communicated these concerns with him? I have. You have. And he gets kind of defensive and you know we talked about this last night and he was like well why haven't you told me any of this? I'm like literally we broke up like two weeks ago and this is one of the reasons. And we started therapy actually last Friday was our first session. A lot of this was brought in as to why I'm not feeling loved or worthy. And it's like not registering with him. Yeah. And I definitely think you should think about it. And I think you, you know, I love that you guys are going to couples therapy and I don't think you're in a position to make a rash decision anytime soon. But I also don't think you need to be dragging this out for

months either. Exactly. I also think while it might be wildly inconvenient and not ideal, and there might be some tough choices and some nights maybe sleeping on a mattress without furniture, you can do it. Yeah. Maybe you can even pick up a second job. You will have some free time on your hands because you won't have a boyfriend to complain about. So you know what Yeah. I know without a shadow of a doubt that I can move out. I can reset. I don't like to use the word start over. You're not starting over. You're just kind of resetting. Having that conversation with yourself saying, I can do this, will free up whatever concerns or fears you have. It'll give you more power. So Madison updated us and wrote, Hi there. Long story short, my ex and I are breaking up. May I just add the breakup was his decision. When I was on the show, Nick recommended I I are breaking up. May I just add, the breakup was his decision.

When I was on the show, Nick recommended I write him a letter. I didn't end up writing a letter, but that night we spoke, and I pretty much said what the letter would have said. That is when ex pretty much said he thought we should follow through with the breakup. I moved into my parents' house, and he moved all of my stuff into a storage unit. I had to find a new roommate, a new apartment. I have embarked on this pretty intense healing journey, which has been paying off. X and I are in no contact, which has been hard.

In brackets, I had to ignore his text. But just found out yesterday he is seeing someone new, using seeing loosely as it's only been two months post breakup. I'm still living with my parents and we'll move back to name of u.s city in mid-february so band-aid got ripped off yeah maybe it fell off in a in in the ocean i i know maybe her story sounds like incomplete you know um maybe for her for for the audience but i I know it's a scary thing to make these drastic changes. And as someone who, I once moved in with my grandma

after a relationship as a 28-year-old man who thought he was, you know, fulfilling his dreams and being successful and making money and had a, you know, fulfilling his dreams and being successful and making money and had a, you know, upscale apartment in Milwaukee and was in this relationship that I thought was going to turn into a marriage. And then we got engaged and if I don't, she cheated on me and blah, blah, blah, blah, blah. And then I moved in with my grandma and I did not like that for myself. And I just, you know, and here I am, you know, a completely different life, and I'm not, you know,

I don't know what's in store for this caller or some of our other callers, but, you know, I think sometimes it seems really scary to take these drastic changes, you know, and like, yeah, okay, fine, she's living with her parents, and maybe that's not where exactly she wants to be, but she knows she can move out. She's already planning on moving back.

She's making a financially savvy choice by not having to pay rent. Yeah, maybe save a little bit of money. And she doesn't even seem all that upset that he's dating someone new. And it sounds like I'd be willing to guess that she seems a little bit more optimistic about the potential outcome. Because the burden of staying in a relationship relationship that just something you felt off but like you're afraid to do anything about it because you're afraid of regrets or the financial implications of an apartment etc etc like no no anything's possible for her and i'm guessing that's going to serve her well i'd be i'd be willing to bet she's a bigger risk taker going

forward in a positive way. Because once you start taking these kind of what feel like risks or these, you know, things that you feel like are just too hard to do, and then you get through it, you know, because you just kind of tackle every day, you know, you're just like, you don't, don't try to think about, oh, how am I going to be happy? Like how, don't think of the end game, just think of the next day, you know, you wake up, right? How do I get through today what what what problems i want to tackle and then i just think it frees you up and i think you'd be you you start realizing what you're really capable of or what challenges you can overcome and i think i think you start putting up with things that you're unhappy with a lot less totally and i feel like so often in these like kinds of transitions we're

aware that they're supposed to be hard, but then when they actually feel hard, it feels like we're doing something wrong. Yeah. And it's like enduring that builds character, damn it. Well, congratulations to her. And I'm glad that you got yourself out of a situation that deep down you knew wasn't right for you.

Welcome back, Renee. Thank you so much back, Renee. Thank you so much for having me. I'm excited to give you guys an update and see everyone again. We're excited to hear it. So remind our callers what your challenge was and what was the advice I gave you. And then we'll play a quick clip to refresh their memory.

For sure. So I live in the same building as the cute neighbor as he was labeled on the podcast. And I was struggling with how to define our friendship and what to do. And I was getting mixed messaging and was very confused. And listening back, we talked a lot about just like the friendship itself and how it's not a real friendship and there's an expiration date on that kind of friendship and how you very much encouraged me to confront this and talk to him about the confusion i was having and just kind of lay it all out on the table so and the harry styles concert was one of those things yeah a lot of confusion to the mix.

Yeah. Let's play a quick clip to refresh our memory. How's it going? Hi, my name is Renee. I am 26 and I'm calling in today. So if you guys remember West Elm Caleb, I have my own version of the tale with my neighbor I just met. So we've basically been hanging out all the time. So the point of the story is we live in the same building and that's when things started to get really

confusing for me. I have a lot of guy friends, but this one from the jump just seemed a little different because of all the time we're spending together. Did you meet in the building? We met in the building. Yes. In the hallway dramatically. I moved in like four days prior and I was coming home one day and I saw this like very attractive man. And I was like, oh, shoot your shot. What's up? We were actually very like platonic for the first month and it wasn't confusing. And I was very comfortable just having a new guy friend. And then let's just say we went to the Harry Styles concert and everything changed. Obviously. As one does, obviously. The man, the sexual energy in the room I don't know something was in the air so you went to a Harry Styles concert and fucked afterwards no so I was very much like I have boundaries like

I won't let things escalate but like that's when it did start getting very like handsy and like flirty and then I feel like after that day we like went on a trip together and it was just very everett on the trip was like are you guys together like just very like handsy touchy so in two days you went to a harry styles concert together and then took a trip it was like two weeks later i think we went on a trip okay where did you go on a trip we went to germany with like a bunch of his friends and my friend. Germany? Yeah.

You went overseas. Well, how many of his friends? Like four of his friends and I brought one of mine as like backup. Backup. Okay. And who suggested the trip?

The first time we ever hung out, we were like drinking and we're like, wait, this would be so fun. Let's like basically take this overseas. You haven't really sat down and just had an adult conversation about what this is. You sit them down and be like, can we talk? And I just

want to talk about us. It's been confusing to me. That's what you need to say. And I think you just be totally honest. And that honesty, it says, you know, when we met, obviously I found you attractive and I thought about the possibility of us dating and see what he says, get him to be honest. Yeah, I did too. You know, like that you, you both acknowledging that, you know, like just put it out there because what your guys are trying to do is figure out how to like, you're trying to talk about it without not talking about it because you don't want to make it weird, but at the same time, you still want to hang out and then you want to take trips together and go to Harry Styles and like embrace the moment. And you both find each other like physically attractive to some degree. And there's

aspects of each other that you really value. And there's a lot of aspects of each other that you really like. And the only thing that I've heard from you about you not being compatible is it sounds like you think he still might be in his fuckboy era. Well, yeah. And I did in your book look for the definitions and I was like, oh, this is hitting. So why don't you just be honest with him about that? To me, what I'm hearing is someone who met a great guy, lots of things you like about him. You're trying to make smarter moves, right? And protect yourself by investing into

fuck boys and you see the signals in people. And so you said, okay, well, he's a fuck boy right now, so I can't date him. So I'm still going to have to try to have this person in my life via a friendship. And then you try to set some boundaries with yourself, which are great, but I think you're also, it's like you're doing all the things right, but you're also not being realistic with yourself. So what did you end up doing? So I, yeah, I thought a lot about what you said. And I was, I feel like that was like a big wake up call for me, to be honest. Like, I think I went in really feeling pretty good about everything and feeling very confident in my labeling him as a

friend and that we had this great friendship. And then like just hearing you kind of break it up, I feel like made me think about it really differently in the sense that I was like, wow, I am spending a lot of energy and time on this person. And kind of like you had this reference to like build a boyfriend kind of thing, which I honestly thought was pretty accurate. like build a boyfriend kind of thing which i honestly thought was pretty accurate so i since then just started taking a lot of space and just kind of like realizing you know um i need to talk to him so i just kind of was pulling back a little and then i was getting closer to talking to him and you know i didn't do it but I have a lot of reasons that like I feel like it was just like I was waiting to do it waiting to do it which I know like is a lot of to do with just

courage and bravery and didn't all the way get there but I kind of just took the steps that I felt like I needed to take to make it feel more normal as like a normal friendship. So I stopped like going over there all the time and hanging out and like the hairstyles of it all like big things like that. I've just tried to like diversify who I'm spending my time with. So you never actually had the conversation with him? Um, no. So like, I'm not gonna say this is why but there was a weird moment we were out together and i feel like a lot of the conversation made me like i was thinking about the conversation and like oh i need to do it need to do it because these feelings are so strong and then um we did

have this moment where we ran into this guy that i used to date and that kind of like confused me a lot more and i was like my head is just so all over the place. So I just- What part of that confused you? You seeing the ex or how he reacted to you talking to him meeting the ex? Yeah, I would say both. Like I saw the ex and I was like, oh, like this is weird.

Cause I felt like I was like, hadn't seen him in two years. Like I physically ran into him. It was bizarre, very New York. And then also his reaction was very weird to me of just like being very like annoyed at that and i was just like i he was annoyed yeah why did and then that didn't spark a a conversation about why he might be annoyed right so like hearing you say it now i'm like oh my god that makes perfect sense a conversation about why he might be annoyed?

Right. So like hearing you say it now, I'm like, Oh my God, that makes sense. But yeah, just in the moment, it's just, I think what it is is I'm just like, what is the outcome of these conversations? It's probably going to be that we need to like take space and time away and like figure our shit out. And so I just, that's what I've been doing. Where are we now with him? Are you still like spending like spending like what what's yeah what's the relationship like um we're still hanging out we're uh i yeah i think i just have been like taking a lot of steps back uh to make it feel more of like a healthy guy friendship but you know maybe yeah we're like making like content together like fun tick tocks like we're

like we're i'm just trying to give us like a purpose and a direction that isn't so like oh we spend every waking moment together so i'm trying to be more intentional about how we spend our time i'm a little worried for this approach that you're taking yeah i feel like what you're doing is trying to find ways to justify you spending time with him past the point of like, you know, it's like, all right, I'm not going to obsess over whether are we dating or not dating. I'm just going to, we're going to make TikToks and content together and I'll find a purpose for our friendship but the end of the day it i don't think the feelings have gone away or the curiosity or your like the interest like if he knocked on your door today and said can we talk and you'd be like sure and he's like i just can we just get it out of the open like i have i first of all i just want to apologize i feel like guessing i've been a little confusing to you and i i i've been working through my issues

and i'm a little scared to say this but like i'm i want to date you i like you i care about you we've been we're making tiktoks together and we're having fun like i feel like you would be very interested in that conversation if we're being honest yeah i mean yeah i'm not gonna i'm not gonna lie on the record you know yeah so that's the truth and that's the only truth that really matters as it relates to this relationship and everything else that you're doing is this a different version of spending your energy on this guy and on this relationship that um allows you to keep him in your life while you build up the courage to like have the conversation you know you need to have with him and i think you're just kind of playing games with yourself

to sustain what you have and then justify it and tell yourself, oh, I'm not avoiding it. I'm not checking it out. I'm just like, I'm pulling back. I'm just doing what I would do anyways. And then, you know, we're, but we're only going to do X, Y, or Z. And like, I won't hang out, you know, and I just, but you're still avoiding, you know, clarity in this relationship.

And I'm guessing you're still spending maybe less energy, but still too much energy wondering what he's thinking or feeling, or you're spending too much energy analyzing how you're acting around him or what you should say around him or what you should do around him rather than just be yourself around him and not you know waste any energy on trying to think about doing, but just being with him and having that security and comfort and clarity with him that you just right now are avoiding getting because I think you're just afraid of the truth. Because once you have that conversation that, you know, you haven't been having, I think deep down, you know, that he's going to say something like, I don't know. I just don't think I'm just not there with you.

And I love what we have, but I just don't think I can get there. that no more making TikToks or creating content, no more spending time together, and no more having that buddy that's been so nice to have at your convenience when you're feeling a little lonely or bored, and you're definitely just taking what you can get, and you're not really getting anywhere with him or with anyone else. And it's, you know,

I think it's costing you more than you realize. You know, this, you know, not getting an answer or not dipping your toes in the water or just jumping in and figuring out how it's going to go. You're really just putting yourself on hold. And I think you're finding new ways to

justify it and explain it to yourself i just think it'd be good for you to like put it out there and know that you can survive this type of communication and and awkward conversation like you you can you can survive this level of potential disappointment. And I still think you can feel good about having that type of bravery because it's hard to do. And it's hard to put yourself out there, but you're certainly capable of doing it. And instead of like trying to read the cliff note to read the tea leaves and trying to overanalyze every little thing, just ask him how he feels and get a straight answer. Yeah, no more tarot readings on TikTok. You know when they always come at you and it's like, I've had too many of those where I'm like,

someone is coming with brown hair. Yeah, I think you should sit him down and be super vulnerable and tell him exactly how you feel. Okay. Tell him exactly what you want and be, and just ask him how he thinks and feels and, and just know that it's, you know,

it's, he's going to have to process that and just stop pretending that his new girlfriend, if he ever gets one is going to want you two to be pals yeah for sure do you have an answer for like that big soulmate question like i'm sure it's been asked but i'm just curious i don't believe in soulmates or anything like that i believe that i i i believe that i owe natalie a lot for us being together and I'm grateful for having realized what she meant to me because I think there's a world in which I could have fucked up and we wouldn't be together and

I eventually would have moved on and I eventually would have found someone else and she would have too and who knows what my life would have been like but that's what I believe and I believe that we have we are given choices and we're giving and we're given free will and we have the right to make certain choices. I believe in regret. I believe, I think, and I think we can learn from our mistakes and I think we can learn from the regrets that we have. And I think there's a million out, the people out there that you can connect with. And, and we have to decide for ourselves who's worth these risks and who's worth these efforts and the amount of energy it takes to be in a relationship

and i think we should be careful about our choices and the time that we have and i think we should use that type of like mindset to like not be so willing to sit around and wait for destiny to happen but we should be willing to put ourselves out there and, and set the expectation of that we want to be prioritized and we're willing to prioritize people who prioritize us. And the best way to figure that out is to express that to the people you're interested in having that type of relationship with and see where it goes and set aside your ego and what it means to be rejected or feel less than just because something didn't go your way. I feel like this would be a potentially good exercise for you to

just challenge yourself. Stop waiting for the perfect time. There's no perfect time. It's never going to feel good or right. It's never going to be like, oh, well, there's no going to be a sign of like, now I should bring it up. It's going to feel good or right it's never gonna be like oh well there's no gonna be a sign of like now i should bring it up it's going to feel awkward it's going to feel as uncomfortable as taking like an ice bath yeah but you know you often ice baths feel pretty fucking good afterwards but it's that first you know that jumping in real fuck it really fucking sucks yeah and i do hear you in the sense that like whether i want to talk about it or not this is taking up a lot of space and energy in my brain and as much as i can convince myself that it's not and that taking space is helping like i still know that like deep down when i think about him i'm like oh like this will happen later in life, but not right now. And it's just like, you never want to have those lingering feelings about people.

Yeah. I think you just need to get it all on the table. Have a little fight with them. I don't know. Okay. Well, get a little messy. Yeah. I mean, life is short. I'm not really scared. It's of like, I am scared of, i'm not really scared it's of like i am scared of i'm not scared like of all people like i know how to fight for something it's more just like i'm really happy living in my little happy world yeah and it's like i want to keep living in it it's not that i'm like scared to sit him down i've done it before it's just i like yeah you're comfortable enough and it's fine huh yeah it's comfortable enough and it's fine and it's keeping it's you're you're content but you have to and we are ongoing theme you know you i think you should be more empathetic

to future you i like that future renee i gotta look out for her yeah and right now i don't think you're giving her much consideration because eventually this this this state that you're content with ends and and the way you're going about it you're you have no control of when it ends it's going to end when he decides it's not convenient for him yeah and i agree like if let's say things work out with this other guy and then i don't want to be sitting there being like oh but i don't know about this and what if and that's not healthy so yeah gotta look out for future renee put yourself out there that's true yeah i mean i'm hearing that i'm hearing that okay I'm hearing that. Okay. There you go. We found something you can hear. I was just, I'm processing in real time. And I just think a lot of it is like, I know you understand what I'm saying. Like, I've just been inundated with so much of just like,

you want, you know what I'm saying? The power of like, he wanted to, he would, and all these things about what we deserve and our self-worth. And it's very confusing at a certain point when you're like, I know that this person isn't seeing this how I am. So why am I going to go after it? But listen, if you, if you thought that and said, Hey, well, I just no longer should be hanging out with them. And I'm going to, if you like, I still think you'd do yourself good by just, you know, even if there was a 1% chance to put yourself out there but yeah like that's not what you're doing you're you're you're just avoiding the conversation but you're still hanging out with them you're still investing your if you were just to move on and be that would be better than what you're doing now but you're not doing that either

right you know you're just doing it to you're doing it to justify hanging out with them you know you're just doing it to you're doing it to justify hanging out with them by just saying well i'm never gonna have this so like i'll just i'll settle on friends yeah yeah and i do think honestly since we've talked i think that's become even more apparent because i've been actively trying to date and meet other people and seeing how i feel and i do think I've been actively trying to date and meet other people and seeing how I feel and I do think it's uncomfortable or weird how often I think about him in those moments. So that's like. Sure.

I think either way, having the conversation will help you process and go in some other direction than where you're going now, which is not really anywhere. Just put yourself out there and just know that if he makes you feel bad or gives you something like, oh, not another one, instead of letting that bruise your ego, it's just more of a, you know what? I don't think he should say fuck you,

but that should be kind of an aha moment for you of being like, you know what? Maybe you aren't everything you're all cracked up to be. It's a selfish. What maybe it's a selfish. What he's doing is selfish on some level. For sure. And I really appreciate that because I think I've been kind of blaming myself a lot for not doing it and not having the courage to do it.

But I think part of this needs to be like me looking at this more honestly, as opposed to like romanticizing the dynamic of just like, oh my gosh, like, well, they won't they, what is he gonna say? And romanticizing him and actually just realizing like, why am I in this situation in the first place? Because this is new to me. Like I've never felt like this about a guy friend.

And I have a lot of guy friends that it's very clear that we're just friends. And I just think, yeah, part of this was this pattern of behavior that I was just falling into over and over with him where he would just like keep putting out these signs that confused me. And I think I need to just lay it all out there for a lot of reasons. But that being one of them of just like, this is why I feel this way. It's not out of nowhere. I didn't just make it up. Yeah. Yeah. I, it's really nice to hear the tidbit though, about you and Natalie,

like congratulations again. It's really nice to just hear that narrative of like it being flipped. Cause I just think we're always being fed these stories of this is what it looks like and to hear you say again how she was so adamant about what she wanted that's like so cool to hear and like it's just nice to hear because i just think we're always this one story of how it goes and like it doesn't need to look like that and i think there's a big difference between chasing and and letting people walk all over you and accepting less than what you deserve and putting yourself out there and confidently stating your expectations and being willing to face possible rejection. I think there's a huge difference between those two.

Mm-hmm. So, all right? Thank you so much. No, our pleasure. Good luck. so much no our pleasure good luck uh well you know it's you know next time give us an update with a little um with you having had this conversation i accept i accept okay and when you do let us know all right take care bye bye we have another update from our lovely caller lily way back episode 438 this was a going deeper episode with Hannah Berner and Lily called in for some texting office hours help. She'd just been on, I think, two really promising dates with a guy and she thought things were going really well. She got a text from him saying that he needed to break things off. He was studying for his CPA exam.

And it was kind of a bummer. And she was unsure of how to proceed. And she was really calling him because she wasn't sure if this could turn into something in the future. I'm calling in because I've been talking to a guy for a while and then it ended. And I'm trying to decide if I should reach back out to kind of clarify that the door would be open for me in the future or if I should just kind of leave things where they're at and then just see if maybe down the line he reaches back out. So you're not even sure if you should text.

Right. You guys only hung out twice. And I know the feeling of having those amazing talks and feel like you're understanding with someone. And you're going to have that again with more people. I promise you. This was like opening your heart up to it. But if you think about it, you were on a fucking high of adrenaline because he was not available. You were not available.

You both were chasing each other like a drug. And you got a hit of it when you first hung out. And it was amazing. And then you did it again but it really was just the dopamine hit of this like chase you guys had and what you're feeling right now is like both of you yes what you're feeling right now is a post like drug feeling the come down the come down of this high of this intense thing but you guys did not hang out enough for you guys to have like actually a stable, normal connection.

It was more of this high of finally meeting. Um, and you did nothing wrong, but he's not your man. Also, you don't even know the more you got to know him, how much you would like about him. Like that's a problem with like someone ending it after the first couple

days. Those are the hardest. It's because now they take that opportunity for you to further get to know him and he broke up with he broke up with you he ended it at a time where you were feeling pretty good so it almost like freezes time with the potential with the potential of what you think they could be and you're locked into that potential of what they am and that that's not who yeah you didn't get to date him see all the shitty sides to him you just have this fantasy of what he is in your head exactly so yeah that's i who he is. Yeah, you didn't get to date him and see all the shitty sides to him. You just have this fantasy of what he is in your head. Exactly.

Yeah, that's, I think, the hardest part is, like, I didn't even get to see it crash and burn. Yes. But you just have that recognition that when you are sad or you're missing those first couple dates, it's like it's not him you were missing. And to Hannah's point, just keep going out there. And you're going to date a couple frogs.

You'll have more bad dates than good ones. But you're going to have another nice date. You'll have more bad dates than good ones but you're going to have another nice date. You saw the best version of him and it goes downhill from there. He said, I called in last June, or possibly May, to ask for advice on whether or not I should reach out to a guy who

had ended things because he needed to focus on studying for exams that he needed to pass for his career. I was worried that I'd not made it clear that in the future I would be interested when we both had more time to intentionally spend together. The advice that I was given is that I should not reach out because it was likely that he was just not interested and wanted to let me down easy. Fast forward to now, I saw that he had liked me on a dating app and was so confused. I ended up matching with him a little over a week

ago and we have been talking ever since and seen each other multiple times. He's been initiating all of the conversation and making plans to see each other and his interest appears to be genuine. I am thankful that we had time to both focus on ourselves for a while because we are both in happier and better place to be spending time together more so than we were last year no matter what happens i think this all played out for the best thanks for the help with this and then she said also to jogs nick memory i came to a book signing about a month ago and told nick that i stuck to his advice and his advice and not reached out the bookstore took pictures and i found these photos very sweet and she attached them to the email. I'll show them to you. Nice.

So I did give her good advice. So it sounds like I'll be curious what he said about his behavior. Well, I think because he, so he'd sent like, I have the text here that she sent in. And the message he'd originally like the breakup message was, or was Lily, I am so sorry to do this while you're on your trip, but I need to get this off my mind. Over the past week or so, I've done some reflection on where I'm at right now. My interest over the last week isn't what it was a couple weeks ago. I have too much going on right now and I've realized that I need to focus on my exam and moving in with my new roommate. There is nothing you did. I just have a change of mind. I'm sorry that I will not be going on this with you, but I want you to know I enjoyed the time that we talked

and got to know each other. I am sorry if I wasted your time during a time when I was thinking differently from now with a lot less going on. I wish you the best of luck with moving forward in your career and as a great person in general. And she had a very classy response. I understand.

Thanks for letting me know. I really enjoy getting to know you. So they ended on a civil interaction. She was just like, how do I make sure he knows this door is open? And I think the advice was ultimately like, he knows the door is open. You've ended things classily. You don't need to follow up text and potentially not read the room and bother him. This is a life lesson to leave things on a high note because you never know what can happen.

Well, yeah. Unless something really terrible happened. You don't have to let people know that you're on standby. I think it's better to let people know that you accept their choice. And it was most likely the mystery of not knowing what she was doing and where she was at that made them like, you know, I don't like her photo.

As opposed to, especially if she was like, well, you know, just if you ever change your mind, let me know. Yeah, that leaves like a lingering taste of like, kind of not as much power as like. As opposed to like, I wonder if she still even gives a shit about me. So yeah, see, great.

Good luck, Lily. I hope it goes really well. I hope it goes well. God, you're playing house. Welcome back, Lily. I hope it goes really well. I hope it goes well. God, you're playing house. Welcome back, Kate. Hi, good to be back. How have you been? What's new? I've been good.

Great. Got some updates. Last time I was on, I was talking about how I was wondering if I should pursue my boss's brother. Oh, yeah. And that he was coming to town around Christmas. And he did? He was a little older? Yes, he's 41. Okay.

Let's play a clip. I think I remember him being like in his, still concerned he was in his fuckboy stage. How can we help, Kate? I am kind of interested in my boss's brother, but not sure if we should cross that line or how to really approach the situation okay so if he comes to town and is flirty and wants to hook up should i hook up with him or no if you know you want to date him you know i guess it depends on what you want yeah if you just want to like have some good sex and like go have some

good sex but if you want to see if he's serious like have some good sex and like go have some good sex but if you want to see if he's serious about dating you then i would maybe slow things down you might be able to have your cake and eat it too but it's it's risky you know i know i feel like the hooking up would be risky it'd be like i kind of would just put myself in that box i think yeah you would have it would have to be amazing sex. And then he would have to, because if you hooked up right away with some confidence, I can assure you that he would pull away and pull back a little bit.

And then based solely on how good he thought the sex was, he would then try to reach out again to see you again, mostly based off the sex. And then over time, you might build a rapport. It would be a slower build towards a relationship. It would delay you potentially being in a relationship. And he has a lot of built-in excuses to not date you. Your boss, the age gap, things like that.

I brought up the boss thing. I was like, I just feel weird about it. And he was like, I don't know. They wouldn't care. He has no reservations on that front. And I haven't really asked him directly, but I think his reservations are more that he doesn't live anywhere near here. wouldn't care he has no reservations on that front okay and i haven't really asked him directly but i think his reservations are more that like he doesn't live anywhere near here and i don't know

if he's like looking today yeah i would just trust your gut on that if he reaches back out i think it's good to show that you're interested in him but other than that it'd play a little hard to get okay because i think it's convenience like i think he's gonna reach out when he's here because totally it's convenient so do you want to be his hometown hookup? Yeah, I guess I need to make that choice. And if I do, then it's fine. Like go for the hookup. But if I don't, then don't hook up. Yeah, I would be real. I think you kind of like him. And I think you would be putting yourself in a vulnerable situation to convince yourself that you just want to hook up. This is why I called. Yeah, I i don't know i don't know if

he's really worth it so your advice was let him pursue me like don't go putting any effort in and like if i wanted to hook up i could but you advised strongly against it okay and okay so he came to town but he like brought the whole family. I mean, boss's parents, which are his parents, sister, brother-in-law. I mean, the house was filled. And so I was like, okay, in a way, even if I wanted to hook up with him, kind of can't, which is a great thing. But he invited you to Christmas. Well, so I was invited by my boss. But he knew I was coming.

So he texted me. And remind me, did your boss know about this? Yeah. No. Oh. Your boss didn't know. But if a memory serves, your boss joked or encouraged or talked about her brother. It's like you guys could be a potential match okay yeah she's like

you should marry my brother and it was like a joke and then she just had no idea i think she had suspicions okay because like when he was in town the next day like i had to do like the drive and drop him off the next morning she knew he obviously slept somewhere else um so i think she has suspicions but she never brought it up to me okay and so i was just like okay we'll let it go and then yeah so two weeks before he came to town he texted me and he was like hey like what are you doing for holidays are you going to be in charleston i was like yeah and he's okay excited to see you so he comes to town but like we didn't really get to talk that much but when we did he was super flirty. He asked me to like, give him a kiss

in front of all of these people. And I was like, Oh my god, like, no, like, I'm not a PDA person, I think. And also, we're not dating. So it was just kind of bizarre. And at one point, he introduced me as his fiance to someone new that we were meeting. And I was like, that's strange. And this was in front of like my boss's husband all of their friends it was okay that's weird did you confront him super weird on on that no because the whole time we're in front of people so I'm kind of like what about after like just my face probably said it all, there really wasn't a time that we were necessarily alone. We had one moment alone where we did end up making out, but then I went downstairs and

I was going to go home, but realized I drank too much. My boss was like, it's fine, stay over. She's setting up the couch for me to sleep on. And as she's doing this, my phone rings and it's him. And she's like, why is he calling you? And then she answered the phone so i think everyone kind of knew what was happening there cringy and then we all went out as like her entire family and myself all went to breakfast the next morning as if nothing

happened wait so was he yeah was he was he calling you from like upstairs like a booty call yeah so he was on like the third floor and i was on the first floor and he like kept calling and like texting for me to come back up there and i just didn't because i was like don't do it kate and then i didn't i was stayed strong good job okay And then you went to breakfast, and then what? And then he pretty much texted, like, I will have to come back to town. It was good to see you. Like, have to visit soon. And I'm just kind of like, okay, I've decided he's definitely in his fuckboy era. Like, that's full-blown fuckboy era.

And have you heard from him since? No. You haven't heard from him since? I have not heard from him since. Good. You haven't heard from him since? I have not heard from him since. Good for you for not hooking up with him. You're a stronger woman than I would have been, but clearly that was the right choice. And did you ever have a conversation with your boss about this?

No. And it's just like, I mean, she answered the phone and that was like, I was like, oh shit. Like I was like, there it is. Like if she had her suspicions before confirmed and she's never brought it up to you never brought it up

to me so what are you going to do when he reaches back out um I think I'm just shutting that one down like okay good no not worth the time but here's the plot twist oh is while at that party Christmas party I met someone else Okay, good. No. Not worth the time, but here's the plot twist. Oh. Is while at that party, Christmas

party, I met someone else and I now could use some pointers with him. So someone else, who else? Because I thought it was his brother? No, it's no one else in the family. It is a

family friend. So getting out of that sticky situation but a family friend of your boss's of her husband okay so still connected to your boss but yeah okay but he has no connection to him no and how did that come to pass um so I was at the party and I remember thinking he's 29 um I remember thinking he was

cute and we talked and like exchanged numbers and then a couple days later he texted and we had like texting back and forth decided to go on date one and it was great like the texting is like he's very attentive he's always asking questions about me not just like small talk and remembers things which is refreshing I mean setting the bar pretty low but it's refreshing sometimes in this dating world so we go on date one and I thought it was just going to be drinks but we end up getting like dinner too

and like conversations good But he ends up getting trashed on this date to the point where I'm offering to drive him home. He tried to make out with me in public multiple times and even did a soft hand on the neck choke in public.

And I was like, whoa. This is a first date? Not much for me. This is a first date. Okay. And I'm giving him the benefit of the doubt of like, whoa. This is a first date? Not much for me. This is a first date. Okay. And I'm giving him the benefit of the doubt of like, he just got drunk. Maybe he was nervous. But then even that is a red flag in and of itself. It's like, he got trashed on the first date

and then proceeded to drive home. Yeah. So did you address that? Yeah. I was like address that? Yeah. I was like, I could drive you. You could take an Uber. And he's like, no. No, I mean like the next day.

Or after. Even the next day, I was just like, I don't think you should have driven. And he was just like, no, I'm fine. Like, I know my limits. And I'm like, hmm. So. Well, if that's true, then you could start inquiring as to like, do your limits include like,

grabbing my neck? Like how many DUIs are within your limits? Well, no, but like, we're thinking about the DUI for a second, not that, but he's suggesting that alcohol was in no way enabling his processing or his

decision making skills. I was like alright fine. I don't necessarily agree but I'll work within those parameters but there are behaviors that he demonstrated to you on that date that made you uncomfortable. I think it was just a very forward first date. Yeah.

Okay. Well, but he did things that made you feel uncomfortable. Yeah. Yeah. Did you address that? You know what I'm saying? Because he's saying,

no, no, this is who I, I know my limits. This is who I am. Like alcohol had no role on, on my, on my choices and decisions or my behavior,

my personality. So that's him telling you that anything he did with you, the grabbing of the neck and kind of aggressive PDA without checking in has nothing to do with alcohol. Can't blame it on the alcohol.

That's just who he is. So I'm really curious curious which one is it yeah i think that's a very good point like is he just like this is me at face value instead of like even blaming it on alcohol he's just like no this is it have you been on like what have you has there been contact with this guy since? Yeah. So I guess that's the thing is like, at first in my mind, I was like, this is a hard no, like that's such a big red flag. I'm gonna pass on it. And then it was just, he would text more and it was like asking, like, how can I help with work?

Like, I know you're working on a giveaway. Like, do you still need brands for that? And just like reaching out and being attentive. And I was like, okay, maybe I'll give him the benefit of the doubt so I was out at a happy hour with a friend and it's like right by his house and I was like we should go sometime and he was like yeah sure like and I'm like okay so are you interested or not and then he was like I'm free like Monday or Tuesday and here we are it's this monday or tuesday and i haven't heard a word about it and we didn't go yesterday we talked about what he did yesterday and he was

like oh yeah i just stayed home and cleaned and i was like okay and i don't want to bring up the date again because i'm like i already initiated going again i don't want to seem like the pushy one who's like so are we still going so why are you so interested in pursuing this at this point? I don't know. I think the texting and the conversations piqued my interest. You know, which is nice, I guess. But, like, there's as many, like,

reasons to call it quits with him too right i mean you're you've only had one date with him one actual day well and then i've seen him in person in like small circles after that you know small circles like what like out we were all out at a bar once and he wasn't getting that trash then and then i saw him at my well how was he house for a football game how was he towards you did he treat you like any other person in the room or did he was he flirting like what was that like he was flirtier but he wasn't doing like the aggressive makeupout thing or the PDA thing, but he was flirty and respectful then. So like, I think that's where I was like, okay, maybe it was just a one-time thing.

But like when he saw you, was he like, oh, I'd love to see you again. We should get together. Like. Yeah. And then we talked about hanging out and texting about it and then it just doesn't happen. Who brings it up? Did you bring it up or did he bring it up? When he saw me in person, he brought it up and then we didn't really do anything about it and then i texted about it a couple days later when i was out yeah i mean i i think that you're he's

not giving you enough to wonder and worry this much about him or the relationship. Which is not worth pursuing. It's not worth investing your emotional energy on and wondering. Yeah, you went out with him. Okay, fine. You question his desire to want to drive home. Maybe you could have challenged him a little bit more about which one is it, but whatever.

Again, he's not your boyfriend. You went on one one date and then you saw him out a couple times you had some like kind of casual conversations like yeah we should hit together sometime but like he certainly didn't like go out of his way and it sounds like you've put yourself out there a little bit and i'm just wondering like what's really there like you know you don't really know him you don't really have there's nothing really like exciting there was not even a good a great first date so i'm just like why like why are we you know trying to make this happen so then do you think it's just kind of like cut off communication unless he like drastically shifts like his energy you know like i don't think you need to be reaching out at all or wondering if he's going to go out with you i think it comes down to hey would you like to go on a date i like you know and and see how his behaviors are on that

second date if he really like tries to make a plan with you. And then checking in from there. I guess that was the thing. I wanted the second date more for myself to feel it out and think, do I want to pursue it? I just wanted another in-person date to kind of make the call. I hear you. But the fact that he's not giving that to you or seemingly all that interest in having it is, I think, information that you could be using to make your decision, but you're not.

You're choosing to set that aside. It's like, oh, well, if I could only go out with him, then I could get more information to make my decision, so I need to go out with him. And that's your mindset, rather than, after one date date he didn't see him all that interested in getting back together with me i didn't even like him on so that much on the first date and he's been kind of wishy-washy since so like all i really know about this guy is that you know he might be someone who over consumes alcohol he also might be someone who uh that affects his choices and his behaviors

and it also might be someone who seems resistant to that reality as well and he's also like possibly in his fuck boy stage and certainly like at least if nothing else non-committal and a bit wishy-washy like that's you know all these things and yet all you're just like you're like oh we had one awkward date and i need to make sure i go on a second date before i really shut it off and you're choosing to just not acknowledge all those other variables that you have seen or those inputs that you could be using to like make a decision on him yeah it's like blind optimism sure you know and i get it like listen we all we want to hope because you know every time we meet someone that we're at least interested in or physically attracted to who seems nice enough and are connected to a familiar face, it's nice to know that instead of a world where we're constantly meeting strangers on dating apps, it's nice that you know so so and there's like you're kind of vouching for that person on some level there's a level of

security i get all that but yeah you feel like they're like vetted sure like okay they can't be that bad but in reality they can just be not compatible for you yeah or like you know we have to not think in this to these absolutes like good or bad evil narcissist or you know wonderful person most of us are somewhere in the middle and and complicated and have moments of selfishness and and you know we can manipulate and use people and then you know we can feel used and you know stuff like that yeah i think it's just the impatience in the in the current dating world you know but i made some good points i don't think he's worth worth the effort yeah i think uh i think uh try to be a little bit more assertive with your expectations and less willing to empathize with with bad behavior early on because you seem a little more a little too willing to empathize

for people who don't deserve it uh and i think if you do that, I think you'll, it'll start attract. It's not something that would attract, but you know, it'll, you might notice a change in the people who you're engaging with, but it will be a direct result of the energy you're putting out. Yeah. Like setting stronger boundaries. Yeah. And that's like a me thing that I need to work on, but I definitely know that that's where that can play a role for me, especially on like first dates. Cause I hate actually like a first kiss on a first date. I feel like it's just like, if you're not into it,

I don't want to do it. Yeah. I mean, they can be awkward and shitty, but they're awkward, but like getting people to be like, no, don't do that. Like, I never want to be like, no. And just my hand up in someone's face. It's like, you be like hey i'm not doing that i mean i i like are you are you finding that a lot of guys even though you're not putting out the vibe they're just they're going yes like on all of my first dates this has always happened guys are just aggressively trying to make out with you yeah like especially at the end like it's like i dread the walk to the car because that you know it's coming and you're just like you give the hug you try to do like the whole avoidance thing and they still find a way and it's never just like a kiss it's like they want to full-blown make out interesting alley yeah you can try and dodge it

but sometimes it's like awkward too it's awkward Hanukkah party guy I was like well guess I'll do this now huh this is a regular thing huh well especially like Hanukkah party guy similar like it was a friend of a friend like I was just like I can't be rude or awkward on this date

because then it's gonna get back to his friends who know my friends and yeah it adds a different element and that situation sometimes what i found works is like beating them to the punch in terms of like just going in for a hug and then being like i had so much fun and then they'll pull you in after the hug and then and then you put your hand no let me finish and then you put your hand out and you say maybe next time and then it's like flirty and fun or something was this from a caller from a friend of mine that was like a really like sexy way to get out of it is to say like, I really want to enjoy like all of our firsts or something. Like someone had a line like that where I was like, oh, not bad.

Yeah. Like I want, I feel like that. I really want to savor our firsts. Especially for like sex stuff. Like as you're like, I want like all of our firsts to be like something we appreciate. Yeah. But I feel like saying that on the first day i know i know it's easier said than done i literally think i'm right there with you what

if we just i literally think that maybe next time yeah like i really feel like maybe next time has always worked for me yeah then it's like a soft no if you put your hand out and say maybe next time and then they go in like that's dangerous and atrocious behavior and like that's like really crossing a line like that's not misreading a room that's like assaulting someone you know yeah i know i feel like it's just like normally what happens is i'll go for the hug and be like thanks so much what a fun time as you're back and they think it's like fun and flirty and like they they think it's like a hot move for sure. And you're like, no, thanks. Our producer, Derek, is saying is suggesting you say like when they try going, oh, you were doing so well.

That's funny. Good job, Derek. A man in a room named Derek. Yeah, I know it can be intimidating and complicated and scary, especially from a man-woman dynamic in that situation. But I hate that you're just going along with it. I feel like some version of some sort of soft no or not just kissing all the guys who assume that they're going to get a kiss on their first date, I think is maybe a good practice. Yeah, I could definitely use it.

I think it's just I never really knew how to be like, you know, without, like I said, just being like a hard no. It was like, what's the polite, non-aggressive way to do that? It's really hard. It's really's really hard it's really really hard and i also think like sometimes like i can feel like all if i was in a situation like that i'll just be like fuck like i'll just be like people please or took over and like shit like i know i don't need to do this and yet in the moment it was so hard to like be unchill or like whatever else and so it is like it's super challenging and i know like you know i'm saying like oh i think this works but it's

like it's very hard to execute it's not just about knowing what to do it's like about having being able to like summon and go against all the conditioning i wish i could uh somehow bottle my uh lack of people pleasing and i don't know yeah you are like the least people pleaser person i've ever met i've ever known well yeah i'm not a people pleaser yeah and i feel like that's why we need this show and i want to make people happy but like i'm definitely not a people pleaser if it if it interferes with my comfort level or boundaries yeah your boundaries are like barbed wire fences like no one's getting across you'll live you know it's a good quality just from the people pleaser aspect i wish i could have a little more yeah you should there's something different about it i don't know what i'm doing you know what i'm? I wish I could bottle it and articulate it in a way.

But I would argue this is such a different beast. I feel like I'm good with boundaries normally, but it's not even like I would describe myself as an over-the-top people pleaser. But it's this type of moment on a date where I just feel like you've been so, I don't know. You never want someone to talk shit about you. You never want some guy to be talking crap about, I don't know. There never want someone to like talk shit about you. You never want someone like some guy to be like talking crap about.

I don't know. There's so much like that goes into it. When I think you were right when you said the word conditioned earlier, we're like, I think we're just so used to like you go on a date. The guy's going to try to kiss you. Like you've known this from the jump. Especially if he pays for dinner and then you're like,

Oh God, I guess this is my payment. So what I think. Society just like, hot breeze. Especially if he pays for dinner and then you're like, oh God, I guess this is my payment. That's what I think. Yeah, and then society's like, yeah, why wouldn't you kiss him? And I'm like, I'm old school. Like, I don't want to. Well, I definitely didn't.

Like, if you're not attracted. Most dates I've been on, like, didn't end in a kiss. But yeah, maybe as a guy, I just had the convenience of not feeling the pressure because the average woman isn't going't I also think you read I think for men you are in like top 10 percentile for reading the room like I think you are like much more observant and like privy to things because like

Maybe it ties into overthinking but like I think you are like much more aware and privy of things in a way that like you'd be Shocked how many men just like do not give a fuck. I don't doubt that, I've known that for a while, but I'm not even thinking about whether she wants to kiss me, I'm just thinking, I don't wanna, I'm not feeling the kiss. You know, like you're describing, it's just like, I went on a date with this guy or whatever, I don't mean I wanna kiss him, just a date.

But you're saying that most of these guys go on dates are trying to like, end the night with a kiss. And I guess I'm recognizing I had the privilege or the, the convenience not to be put in that position because, you know, if I didn't want the kiss, then I was usually not put in a position to avoid a kiss because, you know,

it seems like in most cases, the guy goes 90 or whatever, hitch. I wish that they listened to hitch because they don't go 90, they go 100. But that's what I'm saying. Most women, I say, aren't going 100 for a kiss if I'm not giving them anything. And I haven't been put in that position,

but I can confidently say, I'd be like, what are you doing? What is going on? Maybe that's the lack of people pleasing in me. I don't know. That's what you would say if she was going to go in and kiss you. Let's just say- How are you going to go on a second date after saying something like that? I wouldn't. Yeah. Well, I don't't so that's also going through our heads of like do i just not want to kiss him now do i just need to get to know him better

because if i make too big of a thing of this there's a chance that's dead well i don't want to yeah i don't want why would you want a second date if someone's not reading the room or self aware or checking in or like reading your body language who are putting you in a position to like literally make you go oh my god like because like for 99 of this date like it's been so fun you've been vibing you're like feeling excited you're feeling hopeful and then like there's this moment at the end and like i think in terms of like conditioning like it's very even though like you can again like as a person know like i'm entitled to have all of my boundaries respected and enforced.

Like there is still that part of you that's like, like, am I just like, should I just take the path of least resistance here? Because everything else is great. Okay. Sure. I hear you.

What if, what if, what if it became part of a first date conversations for you? I'm hearing that for the most part, most first dates, you're not super interested in closing it with a kiss, right? Correct. So if a date's going well, like Amanda described, you're just like, yeah,

you're thinking halfway through the date, you're thinking second date. I want to go on, right? And I think when we go on first dates pretty early on the second pretty early on on first dates we've already decided whether we're interested in the second date or not all right so let's say you're in that position you got a first date it's going pretty well half way through the day you're thinking the second date what if you just like in a joking way of being like all right let's talk first kiss on dates. Just make it a part of the dating conversation. It opens things up or like his points of view and dating. And it's just say like, for the most part, I'm not a big kisser on first dates. Just put it out there. And you

know, like, and you don't even have to say whether you plan on kissing him. Maybe it's an opportunity for a flirting. He's like, well, you might want to, no, you know, if I, if you, if we were on a date, right. And you were, and I, and I thought it was going well. And all of a sudden you hit me with like, I have a confession. I am not a big first date kisser. And in fact, it's been my experience that like other guys do this. Like every guy wants to be able to stand out to all the other shitty guys you've been on

dates with. So set them up for success for it's just like yeah this happens why do guys do this do you do this you know and he might you know who knows what he's going to say but you're giving him an opportunity even if it's not true to be like oh no i would never do that i'm self-aware yeah you could even pitch it as like a okay now that i like have you here quick question from a guy's point of view why do they all do this yeah What's going on here? And then that still leaves the door open.

If you're really feeling it after the first date and you want that kiss, and he might be like, oh, so how about that kiss? And you can say, no, I'm good. But I really had a good time with you and I'd love that second date. And all of a sudden you've become someone who's different than all the rest or whatever. You're a challenger. Different than all the rest. And if you decide to lay it on him, you're like, you know, come here, baby. You know, like, I don't know. You know, how about that kiss? You can surprise them. You know, like, just make it part of the dialogue. If it's something that like you're struggling with,

just bring it into the conversation. It's a dating topic. It's something that people are experienced on first dates it's relevant and you'll get his you know you it might open up the door to get his thoughts on women you know how does he talk about women when this topic comes up you know does he get defensive is he more empathetic to your needs or is he defensive to the needs of men you know but it might tell you a lot about a guy on the first date by bringing up this topic that, you know, and then, you know, you're not hoping at the end, whether this is another guy who just assumes he's getting a kiss. I think if you pursue this guy or anyone else,

I think it sounds like you need to work on a little bit more of setting your expectations with people and not waiting on all these guys to figure their shit out. And again, you know, it's been a recurring topic recently. There's a difference between chasing and, you know, acknowledging and putting out what you want, you know, and I think you need to do a little bit more of the latter and just put out what you want, state know? And I think you need to do a little bit more of the latter and just put out what you want, state your expectations and see who's willing to live up to those expectations you're putting out there and move quickly away from the people

who quickly show you that they're not willing to meet your expectations, but rather are more interested in having you around at their convenience. And you are prioritizing too many people who are only willing to have you around at their convenience. And you are prioritizing too many people who are only willing to have you around at their convenience. And you need to start prioritizing people who are willing to meet your expectations.

But you have to put your expectations out there much faster and communicate them more directly and clearly so that you know those people know what your expectations are and then select going forward from there. All right? All right. Thank you so much. Our pleasure. know what your expectations are and then select going forward from there all right all right all right thank you so much our pleasure all right thank you guys all right take care bye-bye okay we also got an update from lily from episode 510 okay Very popular name with our listeners. She was the caller who had ended things with her ex, but they'd maintained a friendship.

And she was wondering if she basically had to break up with them again. Oh, yeah, yeah. Yeah. I think I need to break up with my ex-boyfriend again because we try to be friends, but now I'm in a new relationship. Okay. He might say nothing and he might say something really passive aggressive

and curt. I think that's best case. That's what we're hoping for. Yeah. But if he tries to get into a dialogue that's kind of like, what are you talking about? We're just friends.

Then I would hit him with like, we were never just friends. We had a very meaningful past and that's something I do value him with like, we were never just friends. We had a very, we had a very meaningful past and that's something I, and I do value. And respectfully, like I've had friendships that aren't, I have friendships that aren't complicated by a romantic history. Yeah. And I do, and say, like, I didn't speak for yourself, you know, forget about what his is like, that's, I, I'm not capable of ignoring what we had and I want to be able to value what we had and not try to, you know, pretend to be just friends. All right. We'll see. I feel like his,

I don't know what he's going to say, but it's going to be something sad. I feel like. Let him be sad. Let him be angry. And this is where you have to be the bigger person and allow him to think of you as the bad guy. This is where you have to let go and not wanting to be the bad guy got you into this situation in the first place. Totally. So let him talk his shit or hopefully he doesn't say or do anything that is hurtful, but he's going to be hurting and just let him get it out. You don't need to be the greatest person in the world to him anymore. So the text that we recommended her sending was something along the lines of,

after giving it some thought, I'm not sure that us catching up is the best idea. I've started seeing someone and I want to focus my energy on that relationship. I've always valued our time together and our friendship, but I don't think it would be appropriate for us to catch up. I hope you understand. So he was asking to meet up and catch up, and she attached some screenshots of his response. What did he say? He said, No worries, I know you're busy and that things are a lot different now. I want you to know that I wasn't planning on a long, sappy phone call

because of your post or being in some type of mood. Now I realize I hit you up on the same day, but I only reached out because November 1st was exactly a year since we split up. So I thought about you, and I just wanted to chat for a a bit I actually didn't see your post till the next morning then felt really stupid for texting you because I realized how it looked lol so if you're down to just chat and catch up obviously I'd love to you're always free to call anytime but if not I totally understand and will respect that Lily did not answer then looks like a few weeks later potentially uh late november sent some photos of some pets some dogs and a cat he did yep and his caption was hey i thought i'd

share some pics from last week smiley face and then a month later he said hey merry christmas on christmas and happy birthday to i'm assuming a pet name too is that it so yeah um she said i'm confused by these messages because one we broke up before november 1st so i'm not sure what he's talking about in the first message and then he continued to text me over the holidays i guess i expected this but it was also annoying because i was hoping the message we sent him would stop him from contacting me as often. I think she's doing the right thing of not responding. Yeah, because this is not ghosting.

She gave him the explanation, and so she's not going to respond to these messages. She doesn't know that. I think the non-response is very appropriate. Good job leaving him on read, Lily. Yeah. I mean, you know, he he's not and that's fine he he's going through his own journey but eventually he'll figure it out yeah i don't know

i don't know why he feels the need but i think the important thing is there's nothing really to be confused about other than like yeah breakups are hard and everyone goes to their own journey and I don't know why he's having a hard time fully letting go. But yeah, he's just having a hard time fully letting go. But the good news is that she either knows that she needs to fully let go and is willing to follow through with it better than he is or has already done that to at least a least a certain extent it's great love that

thanks for listening don't forget to send in those questions at asknick at thevilefiles.com make sure to check out our amp show better date than never every thursday at 9 p.m eastern jim jeffries on tuesday for bachelor recap theners on Going Deeper on Thursday. Thanks for listening. We love you. We'll see you tomorrow.