The Viall Files - E592 Ask Nick - I Need To Stop My Soulmate’s Wedding

Episode Date: June 5, 2023

Welcome back to another episode of The Viall Files: Ask Nick Edition! We’re back to answer your burning questions about the world of dating and relationships. Before getting to our callers, we read ...an email about lifestyle compatibility - our writer lives a fast paced life in the city and has been talking with a guy who lives a much quieter life an hour away. Is that a red flag, or a way to balance each other out? We then get our Breakup Song of the Week submission.  Our first caller’s soulmate is marrying someone else, and she wants to speak now before the wedding. We end up drafting (and sending!) a long text message where she confesses her feelings and asks if he would consider trying things again. Our second caller wants to break up with her boyfriend of nearly five years, and he doesn’t see it coming. There have been problems throughout their relationship, including him not wanting to go to a wedding with her because he won’t know anyone there and she isn’t fun enough to make his experience enjoyable. Our final caller matched with her boss on Hinge and is interested in him, but isn’t sure what her next move should be. They bantered back and forth in the messages, but she was the last one to reach out.  “I don’t think you can go too hard here. You’re literally trying to break up an engagement.”  Start your 7 Day Free Trial of Viall Files + here: https://viallfiles.supportingcast.fm/  Please make sure to subscribe so you don’t miss an episode and as always send in your relationship questions to asknick@theviallfiles.com to be a part of our Monday episodes.  Join us for our new LIVE show on Thursdays at 9PM ET/6PM PT on Amp, available in the Apple app store and https://www.onamp.com for Android listeners. To Order Nick’s Book Go To: https://www.viallfiles.com  If you would like to get some texting advice on Office Hours send an email to asknick@theviallfiles.com with “Texting Office Hours” in the subject line!  To advertise on the show, contact sales@advertisecast.com or visit https://www.advertisecast.com/TheViallFiles  THANK YOU TO OUR SPONSORS:  Caraway - Visit https://www.Carawayhome.com/VIALL to take advantage of this limited-time offer for 10% off your next purchase. This deal is exclusive for our listeners, so visit https://www.Carawayhome.com/VIALL or use code VIALL at checkout. Caraway. Non-Toxic cookware made modern. Grammarly - You’ll be amazed at what you can do with GrammarlyGO. Go to https://www.grammarly.com/GO to download and learn more about GrammarlyGO.  Babbel - Right now, get up to 55% off your subscription when you go to https://www.babbel.com/viall Article Furniture - Article is offering our listeners $50 off your first purchase of $100 or more. To claim, visit https://www.article.com/VIALL and the discount will be automatically applied at checkout. Episode Socials: @viallfiles @nickviall @alison.vandam @liffordthebigreddog @dereklanerussell

Transcript
Discussion (0)
Starting point is 00:00:00 you're crazy what's going on everybody welcome back to a new and exciting episode of the vile files ask nick edition i'm your host nick joined by the household of Allie, Amanda, and Derek. The team's finally back. Derek's back from jury duty. Anything you want to share? Oh, Derek, your mic's off, isn't it? Yeah, alright. Were you silent? Or were you silenced? Derek was silenced.
Starting point is 00:00:36 Derek's mic's not on. Just yell, Derek. Hello! Okay, there we go. Derek's back from jury duty. Thank God. What's new? what's going on what's cracking what's what's happening well we got quite a we got um a write-in that i thought was like a very good discussion topic because it pertains to lifestyles and compatibility and so this person wrote in saying basically they'd reconnected with someone from who they'd
Starting point is 00:01:01 known in high school matched on bumble They've been talking starting to date, but they have some concerns about like overarching compatibility. So what they wrote was, I live in the city. He lives an hour outside of it, basically where we both grew up. When he came to see me in the city today, he was kind of overwhelmed. I had the feeling he was quieter than usual. All the cars and buses. The bright lights. I had a feeling he was quieter than usual. Maybe it was just the nerves, but he kept saying how crazy the city is and how many people are out and about. I didn't even notice it. For me, this was a very normal daily life. He lives a very quiet life. He's doing his master's degree right now while working part time. He goes to the gym a lot and loves motorcycles. He spends his weekends going on motorcycle rides and he has a few close
Starting point is 00:01:45 friends nothing too crazy rarely goes out spends a lot of time with family goes to sleep early gets up sounds like a hoot how old is this guy we don't know the age 87 how old is she 42 we don't know the age not many people disclose their age unsolicited okay if you but if you want maybe if you're writing in to ask nick i feel like like, yeah, the people who write in, they should know the show by now. Well, it's like the Reddit threads where it's like, I, female, 25. Sure. Yeah. But anyone who's written in, I'm assuming at this point, has listened to the show.
Starting point is 00:02:12 And every call starts with, fake name, real age. I feel like I try not to judge people based off of age. Unless it's sometimes we- We've been literally doing that since the beginning of the show. No, but in terms of assessing the juiciness. It's not judging them,. It's a data point. The data point. And in a lot of situations it's an important data point.
Starting point is 00:02:30 Because if nothing else, either you're the rule or maybe the exception to the rule, but like it's, you know, it matters. In this particular situation, yeah, like I want to know if this guy's like 23 or 42. Okay. Actually, sorry. She's 27. Okay.
Starting point is 00:02:44 It was on the top of the page. It was cut off. They grew up together? Yeah. Like knew each other growing up. So he's about 27. Okay. You ask me follow-up questions. Like I've been out to dinner with these people and like, I can be like, oh my God. Yes. That is my presumption. Yeah. So her, on the other hand, my life is very busy. She says my work work hours are different every week and I work in live video production. I have several different friend groups that I see regularly. I go out for dinner two to three times a week and a club once a week, maybe once every two weeks. I love to party. When I drink, I start smoking. I also love to spend time with my friends, especially my closest ones who live in the same building as me. Even finding time to date, even though finding time to date isn't easy, it's still something I want. I stay up late, I get up as late as I can, and I do go to the gym as well. So right now, I don't know if I'm looking for someone that lives that busy life with me and goes out to party with me,
Starting point is 00:03:41 or do I need someone to kind of settle me back in and just give me some peace in life? Is this someone she's been dating or? Well, they matched on Bumble. They knew each other growing up and they matched on Bumble. So clearly they're both looking for something. And they've been talking for a few weeks now, is what she says. So I was just curious,
Starting point is 00:03:58 because I do think that's like the big question of relationships is like, which areas do you want to have someone who balances you out, is maybe different, has different strengths from you? And which areas is it just easier when there's alignment and so of the kind of things that she mentioned the lifestyle differences do people any strong thoughts or opinions on which ones would be the most significant lifestyle differences which i mean i just ended something because of compatibility so i feel like i'm like
Starting point is 00:04:22 move on say more it's just like sometimes you just don't, I don't know. I was getting so annoyed by how different our schedules and lifestyles were. Yeah, I mean, that matters. I think this particular person is overthinking it a little too much,
Starting point is 00:04:37 too early. Yeah, although I would be pretty taken back if I was on a date with someone and they were like, oh my God, the city is just kind of overwhelming right now you know I mean if you live on in the countryside it's gonna be like a bit much I don't know wouldn't judge this person it would just be like not the vast majority of people I interact
Starting point is 00:04:57 with would not have that reaction so yeah it would probably what is that what are they asking what's the question yeah that I don't know if I'm looking for someone that lives this busy life with me and goes out to party with me or if I need someone to settle me back in and just give me some peace in life. I can't figure out if these opposites are a positive change or if I need someone to match my energy. Well, I guess it depends on where they are in their life and what do they want out of it.
Starting point is 00:05:20 Yeah, because it seems like she's happy with her current. Sounds like she likes her life. Clubbing and going out. So I'm not sure why she's questioning if she needs someone to settle her back in if she's so happy with where she's i don't know the settling back in oh and she can like when you date someone who's a good influence just in like certain habit and lifestyle is there something wrong with her influences right now yeah it feels like she's thriving yeah like she's doing everything she wants to do her thing she's like that tiktok noise where it's like i smoke i drink i fuck bitches i that's her but it's not like she's like 39 writing in and being like i just like can't help but go out and party all the time and i just need someone to like
Starting point is 00:05:56 pull me back to reality good influence doesn't imply that she is like out of control or is inherently bad it just means that like the way this person would show up in her life might be positive changes in terms of like going to bed a little earlier, like on certain weeknights, you know, like things like that. Like it sounds like this person don't have a partner to like get you to go to bed on time. I feel like actually that is I that's something I really think about with a partner is like, how do they encourage me to maintain wellness practices that I have? And how much is that also a priority for them? I think overall, dating someone who you think takes care of themselves. But she's not describing herself as, to Allie's point, as out of control.
Starting point is 00:06:41 Where she's just like, my life's falling apart. I have no guidance. But I literally just said, it doesn like, my life's falling apart. You know, I have no guidance. But I literally just said, like, it doesn't mean your life is inherently bad. It just means that the changes that people bring could be like positive. Like I think for this, and it also doesn't need to be radical or maybe it's just like every like once a month instead of having the club night, she has like a quieter night in. No, I hear it. I'm just saying as far as this particular guy, I think she's probably overthinking it at this stage because i i do think the fact that they lead drastic lifestyles if nothing else is more of a if anything it's a red flag because i do think
Starting point is 00:07:16 from a compatibility standpoint it might be too much for one of those people yeah like either he's just going to be like i don't want to come to the city all the time to hang out with you. And while she likes that he's responsible and things like that, and maybe she's thinking herself, you know, maybe I could go out a little bit less. Like ultimately she'll stop going out when she wants to stop going out, you know? And it sounds more like she likes the idea of what he brings to the table rather than actually when she's ready for it
Starting point is 00:07:45 she'll be ready for it yeah let's say she starts to date this guy and he has healthy habits whatever those healthy habits are yeah like she can pull from that and vice versa but i don't think you date some like the idea that she's going to date this guy specifically for how much he is different from a lifestyle standpoint is is a way to try to mimic that behavior more well i think the thing is they're already vibing they get along they're talking now this has come up because he went to the city it kind of exposed this incompatibility and so now that it's like we already know that we get along as people so it's like would this be a positive thing would this be a negative thing? Would this be a negative thing? Is this a non-issue of these lifestyle differences?
Starting point is 00:08:28 Also, do we even know if it's a compatibility thing yet? Either. He is in grad school. So it just could be a product of the intensity of this program where he's just like, I just got, I work. I want to stay in shape. He goes to the gym a lot. And he says, I don't have fucking time for it.
Starting point is 00:08:43 Yeah, I think we need more time and data points because as nick was telling me when in my situation he was saying like it's it's one thing to have different lifestyles but is he willing to try the city is he willing to stay up a little later like you haven't seen when he does go out yeah is he a good hand can he put himself out of his comfort zone? Is it a matter of like, I just, him being super introverted where he's just like, he's like a fucking social liability and you have to constantly worry if he's okay?
Starting point is 00:09:13 Or does he shine? And him not going out is just a matter of him, again, just being too busy. And as far as like the bright lights of the city, maybe he just has to like hang out there a little bit more.
Starting point is 00:09:24 How much do you feel like you guys individually will kind of potentially alter your lifestyle based on a person you're dating? Obviously thinking back to your days when you were dating multiple people, like the different people that you've dated before. What's the question again? Just like how much do you feel like your own lifestyle?
Starting point is 00:09:42 I was dating multiple people. When you were the bachelor. When you were a huge fuck boy. No, I just mean like in terms of when thinking about the various people you dated throughout 20s, 30s, whenever. When you date someone, how much do you feel like you kind of adapt your lifestyle based off of their own lifestyle practice? Zero.
Starting point is 00:10:03 Yuck. Yeah, I never adapted to anyone i mean i would like stay up late because he wouldn't get off of work until a certain time which i hated doing yeah i would like make yeah i would try to like make shit work i like to go to bed at nine he didn't get off work at nine i will stay up until midnight on a weeknight even though it makes me want to die okay yeah that's not sustainable i guess i never dated someone where it was like we were that off in terms of different schedules wait can i say a fear that i have that is probably me overthinking things which is i need to be walked like a dog truly i need to move like i need to move i am not a functional competent or happy person if i don't like move regularly
Starting point is 00:10:45 and i love going for walks and i feel like my boyfriend doesn't like we have definitely yeah you've taught we've touched and i'm still on my mind what do you mean she says this before she needs to be walked like a dog i need to be well i say it with love she does and when you say you need to be walked like you can't she has to walk i can go but it's like if i'm spending like a weekend with my boyfriend yeah it's also obviously i can do it on my own and oftentimes it's like a good he hates walking he's just not into it yeah he doesn't gravitate towards it well i wouldn't call myself a walker but if i were dating someone who identified as a walker you would go on a walk i would walk yeah how long are these walks?
Starting point is 00:11:25 Amanda can go for a long time. I've been on walks with her. She one time lost her Invisalign in West Hollywood. We had to retrace our steps. We found it. We did. So like to walk with you is like a whole. It's a journey.
Starting point is 00:11:36 It's a couple miles. It's a few different things. It's like I would rather walk. You're running errands? Well, I would rather. It's a few different things. You want to go on a walk? Next thing you know, you're at a dry cleaner
Starting point is 00:11:45 you're in North Dakota that would be a nightmare it's you gotta go for a hands-free walk that's part of the charm I think so there's like
Starting point is 00:11:53 quality time walks scenic walks there's like sheer necessity walks there's like functionality what's a sheer necessity walk that's like I'm going crazy
Starting point is 00:12:02 she had one yesterday gotcha get out of the house she had to go on a quick pace like I need fresh air i need to move like this is this is not those i like those totally like a little power just like a yeah but then i'm always one who's like net let's not uber let's just walk it's 20 minutes it's fun i like that but like a two mile expedition, like a 40 minute walk. I love it. Yeah.
Starting point is 00:12:28 She could go for a long time. Thank you. And this is a requirement to date you? Well, it's just something that I find myself feeling anxious about. Well, first of all, I think I'm constantly thinking about the future in a way that I'm like, I'm not sure if this is healthy and I think I should maybe be living in the present a little bit more. But I'm just like...
Starting point is 00:12:44 With the walking part? With the walking, walking i'm like so is my whole life gonna be thank you for translating for me she's thinking am i gonna be 65 walking alone in the suburbs of new york i think you can find a walker but maybe nick's not your guy oh my god load it sounds it sounds like this is very important to you like here's my question how happy would it make you if he shared in your enthusiasm to walk i would be thrilled like on a scale of one to ten we're talking 12 here no we're talking seven so it's not that exciting you no sorry i'm for the listeners i'm pointing my finger at nick right now because i just this like past week we were talking about how people inflate on scales of one to ten how people are
Starting point is 00:13:33 always like yeah but not everything's above average seven's above average above average but i thought like as someone who's describes himself as needs to be walked like a dog, who is his burden with these lonely walks. It's not the absence of him. And if you could have a partner that shared in your enthusiasm, I was expecting more than a seven. Well, I was kind of thinking about all the other things that you could ask. Well, I was kind of thinking about of all the other things that you could ask. Like I didn't want to put walking at a 10 because I'm sure there are things that are like much more where it would be much more impactful for someone to have enthusiasm. Like if someone is enthusiastic about my family, like really enthusiastic and like genuinely like I feel like that's a 10, you know?
Starting point is 00:14:22 What's his skill set enthusiasm? Like how enthusiastic is he as a person? Can he be? Yeah. Like I'm a zero. Like a one. Maybe. Yeah.
Starting point is 00:14:32 I would say, yeah. You're more than a zero, but it's not high. It really is. If I feel like that's fine, I'm exploding on the inside. Um,
Starting point is 00:14:42 he's passionate, but not enthusiastic. He's a chill dude. He's chill. Yeah. But he's, he's enthusiastic he's a chill dude he's chill yeah but he's he's more than Nick for sure that doesn't take much
Starting point is 00:14:51 he's also he loves to be like he loves to drive like he's the one like he'll organize his friend group great sex or great walk oh
Starting point is 00:14:59 well okay here's what I'm again I'm immediately thinking about a lifelong partnership no great sex great walk no no I think more Well, okay, here's what I'm, again, I'm immediately thinking about a lifelong partnership. No. Great sex, great walk.
Starting point is 00:15:07 No, no. Instinct. I think more life partner. So are we saying, so for the duration of the relationship, great sex or like extreme walking compatibility or like right now, great sex, great walking. For the next 20 years. And it's guaranteed great sex? Like your hip gives, yeah. Well, you know, you need a hip for walking and sex. Great walking. For the next 20 years. And it's guaranteed great sex? Like your hip gives, yeah.
Starting point is 00:15:27 Well, you know, you need a hip for walking in sex. Yeah, I'd say great sex because it's like, I'll call my mom on the phone while I go for a walk. But I'm not calling my mom during sex. Yeah. I played Heads Up on Memorial Day. Guess who came up on Heads Up? Nick Viall. Nick Viall.
Starting point is 00:15:41 And everyone just screamed, You're boss! Oh, I'm on Heads Up? Yeah. Nice. Yeah, in the Bachelor category. Nick Viall. And everyone just screamed, your boss! Oh, I'm on Heads Up? Yeah. Nice. Yeah. In the Bachelor category. You made it.
Starting point is 00:15:49 Not in the general category. There's a Bachelor... Yes. Oh, so just the whole show has a category? My friend got drunk and paid $40 so we could have every deck on Heads Up. All the expansion packs. That's definitely less cool.
Starting point is 00:16:01 Well, you're there. I thought I just made it in general. Sorry. I'll let you know if you pop up on other ones. Okay. Should we get to our callers? Let's get to our callers. Oh, by the way.
Starting point is 00:16:10 Oh, no. Sorry. Breakup song of the week. Oh, no. Also, housekeeping. We're not going to preview our guests this week for fear that they might be removed from our lineup via some networks. But we do have a great week lined up for you.
Starting point is 00:16:23 We can't wait to share all about it. Get ready for another amazing sizzle drop from the one and only Allie. We have a new update for all you update lovers out there. We dropped one last week. I'm sure you listened to it and loved it. We dropped one last Friday for Vile Files Plus.
Starting point is 00:16:43 Again, remember that every month we drop two additional updates behind Vile Files Plus. Again, remember that every month we drop two additional updates behind Vile Files Plus. In addition to the one that we drop every month on Vile Files Classic, it's free to sign up. You get a seven-day free trial. If you haven't checked it out yet, I don't know what you are waiting for. By the way, I just started watching Vanderpump episode one, season one, and we're going to start recapping that on Vile Files Plus. It was a really good first episode. It was strong.
Starting point is 00:17:10 It's good. Shout out, Kristen. Yeah. It's really weird watching like the early seasons knowing what we know now and like knowing who the major players are. Also, I love that like Tom Sandoval,
Starting point is 00:17:22 like I think one of the first things he said was not like, it was following, i think katie talking about wanting to be like a musical artist and then sandoval was like i just want to be a celebrity and he's wanted to be famous that's all it was his only at least he's honest yeah he was vague but yeah no sense of like real just he just wants to be famous and love and i guess that's how you start a cover band god and speaking of covers and songs well and you know who and you know who specifically is going through a breakup right now mr tom sandoval he does not get to listen to this this is for ariana only um someone submitted an awesome song called spread thin by mariah the
Starting point is 00:18:02 scientist uh they said this song uh was the song that got me through when I broke up with my ex-boyfriend of three years. If you have ever been lied to or lost trust in a person that you once loved, this song is for you. Lyrics to belt at the top of your lungs while driving with your windows down. Baby, you're the reason you always think the only one who needs attention is you. Don't be so conceited. I hope you learned honestly was the only thing that could keep me from leaving honesty fuck me i you want me to just read that again so it's really like me no i feel like i've
Starting point is 00:18:35 i've been shocked that nobody comments on my like glaring dyslexia and it's like diagnosed i'm running cover for you what's that called i feel like there's a specific word And it's like diagnosed. I'm running cover for you. What's that called? I feel like there's a specific word when it's like you make a big scene to hide the sneaky thing. A Trojan horse? Yeah. Distraction? A what?
Starting point is 00:18:57 A diversion? A diversion. Yeah, I think Trojan horse is what I was thinking. Nick is your Trojan horse. All right. Well, let's get to our callers. Question time with Nick. Let's ask Nick your sexy questions.
Starting point is 00:19:15 How's it going? Hi, how are you? Good. What's your name? I'm Haley and I'm 26. How can I help Haley? My soulmate is marrying someone else. Oh, shoot. Okay. Okay. Why do you think thisaley? My soulmate is marrying someone else. Oh, shoot.
Starting point is 00:19:25 Okay. Okay. Why do you think this person is your soulmate? Well, it's a pretty long story. We met about seven years ago. We kind of had like an on and off again sort of situationship. And I feel like I haven't connected with anyone else as strongly as I've connected with him. And every time I date someone new, I always compare him back to that person and no one's really matched up since then.
Starting point is 00:19:50 Okay. Understandable. He also, if I heard you right, was in a situationship with you for how long? So the first time we met, I was a sophomore in college. He was a senior. We met my first week of sophomore year at a party. We instantly hit it off. I was on the verge of a breakup with my high school boyfriend. After meeting this guy, me and my high school boyfriend broke up a couple of days later. And then me and this guy started talking every day. I visited him at college pretty much like every weekend for about four months. So the situation at that time lasted about four months. And then we decided to break it off the spring semester of my sophomore year because he was considering moving away after he graduated college and didn't want to
Starting point is 00:20:38 start a serious relationship. And then what happened? relationship. And then what happened? So then a few months went by and May rolled around. So he was a senior. He graduated and then he reached out to me and said that he had decided that he wasn't moving away and was staying in the same state that we were both from. And he wanted to try to rekindle things. So that was in the summer. We had hung out a few times, but I started a new job and I met someone at my job and I actually started a new relationship. So we kind of lost touch for a few months. And then that relationship that I started was very toxic. A lot of cheating, emotional abuse. It was not a good relationship, but it did last. It was on and off for a really long time. to last really it was on and off for a really long time um so throughout that relationship um the original guy came back into my life my junior year of college and wanted to really like give
Starting point is 00:21:31 things a shot but he still wasn't fully ready for a relationship but he wanted to see where it would go um but I kind of shot him down because a he was a little hesitant to be in a relationship but mostly because I was so caught up in the toxic cycle that I was stuck in with my boyfriend at the time. And that was like a really big regret that I've had since then. So in your mind, you kind of ended things. Yeah, like he wanted to kind of give it a shot and I didn't invest in it because I was just too caught up with that toxic relationship.
Starting point is 00:22:07 How long ago was that? That was in the end of 2017, beginning of 2018. So five years ago. Yeah. But then, so then after I kind of shot him down, he started dating someone else a few months later. And then we didn't talk for a really long time. And then, um, Labor Day weekend of 2020, um, he had reached out to me. Um, he was still dating that girl. I was still on and off with the toxic ex-boyfriend.
Starting point is 00:22:37 And he asked me to come hang out with him and his friends. So we tried to just be friends. Um, we hung out a bunch of times, but he never brought his girlfriend around me so i never met her um and we hung out a bunch of times like celebrity weekend we went out it was a little shady yeah yeah um went out for labor weekend went out for halloween like a bunch of random weekends in between then um and then he had told me that his girlfriend got accepted into grad school like really far away and he was following her there um so he had a going away party with his guy friends and invited me and one of my girlfriends again his girlfriend was not at the party um we ended up kissing that night um he wanted to take it further and i shut it down and i was like you're in a relationship i
Starting point is 00:23:24 don't want to do that i don't want to get messy he cheated on his girlfriend yeah he cheated on his girlfriend um he wanted to take it further i said no um and we kind of just like had a long talk and he said that like he tried to rekindle things with me my junior year and i kind of shot him down like i told you because i was dating someone else and i kind of questioned him i was like do you see a future with this girl like why are you moving so far away with her if you could so easily cheat on her and he couldn't really give me a straight answer the only thing he said about his relationship was that he loved the dog that they had together um and he had already told everyone that he was leaving and he kind of like felt committed and he couldn't like back out of
Starting point is 00:24:03 leaving with her um so he said obviously it's too hard for us to be friends i left the party and then a couple days later i saw he had deleted me on all social media and like removed me as a follower so i was kind of hurt by that because we had been in each other's lives for so long so i texted him and i was like it's kind of cold for you to just cut me out as if nothing happened um yeah but that was more you know him trying to move on i mean you know i guess yeah you know he shouldn't have invited you without his girlfriend being there he was lying to himself about wanting to have a friendship and lying to you about like trying to be friends you guys he cheated on his girlfriend with you he would have been willing
Starting point is 00:24:43 to go even further than just a kiss. You rightfully, you know, called him out and stopped him from getting even worse than it was. But you both played a role. He had a low character moment. We'll call it that. And hopefully that moment, you know, was like, what am I doing? You know, like whether regardless, like I fucked up. And the right, I mean, quite honestly, if the right thing for him to do,
Starting point is 00:25:07 it was exactly what he did, was to, he should have blocked you. And it has nothing to do with you. It's just more, I can't tempt my, this was wrong for me and I need to, you know. So quite honestly, you should be happy that he had a correct reaction to a low character moment. You know, your ego doesn't like that, but your ego doesn't really care about your character or his.
Starting point is 00:25:33 So, yeah, I think you should see that differently. Anyways, he called you. Go ahead. He called me. Yeah, that's a good point. I never looked at it that way, that it was kind of probably the right thing for him to do. So he called me and we were kind of just going back and forth. And he was like, well, like, what do you want me to do? Like, what, what, what should I do? And I kind of just got mad at him and I was like, you know what, do whatever you want,
Starting point is 00:25:53 like have a good life hung up on him. And I kind of wish I would have been like, don't go, like, don't leave with her. Like, I feel like, you know, we always keep coming back into each other's lives for a reason. And there's obviously this like undeniable chemistry and spark and feelings. But I didn't say that. And then we didn't talk for like over a year. And I was still thinking about him. And I kind of didn't like how we left off on bad terms. So last summer, I texted him.
Starting point is 00:26:19 And I was just like, I want to apologize for yelling at you and hanging up on you. I was just really upset. And you meant a lot to me. And I, you know, I wish we would have got the timing right. But if you're happy, I'm happy for you. And he said there was no hard feelings and he wished me the best. And then I found out a few months later that he was engaged to that same girl. How long ago was that? I think I found out in the fall of this year. Well, I don't know.
Starting point is 00:26:45 What do you think? I mean, listen, like you have one option. Go big kind of thing. That's what I'm kind of like. Should I just text him and lay it out on the table? Like that this is how I feel. And I thought we could have something great. Well, before you do that, like how certain of your feelings are you about this?
Starting point is 00:27:01 Or is this, you know, you reminiscing about the past and certainly yeah there's justifiable reasons for you to have regrets you know i wish i would have held this situation differently you truly have no idea how how he would have reacted to any of your you know going back in time you know you could how do you want to have this you're gonna be like well i don't want you to leave he could have just easily been like i don't really know and still left because i i don't know so you don't know either so you know you can regret it but there's no point in you beating yourself up over it back to the original question it's just like the fact that you've been going out there
Starting point is 00:27:40 and dating around and meeting a bunch of other guys and them not comparing to him, I don't think that's meaningful at all. I think that is a mistake we all make because you are only looking for one, right? And I strongly think there are more than one person in this world for us to connect with, have chemistry with, have, you know, I don't believe in soulmates. I know this all started with, you know, soulmates, but that's just a personal preference. I have no doubt that this is a guy that you have a very natural chemistry with, that there is a strong connection between the two of you that I have no doubt.
Starting point is 00:28:17 Right. Uh, but you both made choices. Our choices matter. We can fuck up our lives, so to speak, but we can learn from our mistakes. Um, and so I guess back to what I was saying it's just like you're only 26 just because you've been on a bunch of shitty dates you just been you just been on a bunch of shitty dates with guys who weren't your guy right but if this guy moves forward with this wedding it is in no way mean that you're not going to find someone at all. You know,
Starting point is 00:28:46 you're just, it's just not going to be him. Right. So you really have to ask yourself, is this really about him or is this about you just getting impatient with your love life? I mean, it might sound naive, but I really do think it's about him because I have met other people that I have connected with. It's not that I'm like totally like given up on dating. And what would you be willing to do for him right now? Because for you to go in there and risk fucking up someone else's life, this other woman. I know that's like what eats at me too. Like I don't want to be the.
Starting point is 00:29:21 It is what it is. Either he, either that's, that's mostly on him. Really? Honestly, if he loves her, then you're, he's just going to be the... It is what it is. That's mostly on him, really, honestly. If he loves her, then he's just going to be like, yeah, sorry. So it's on him to decide whether what you have to say to him matters to him at all or not. That being said, if it does rattle him at all, you need to be willing to do anything. You know what I'm saying? Are you willing to move? If we were really going to give it a real shot, yeah, I would be willing to do anything. You know what I'm saying? Are you willing to move? If we were really going to give it a real shot,
Starting point is 00:29:48 yeah, I would be willing to do that. Okay. Most likely what will happen is that you shoot your shot, you don't get the reaction you want, and as disappointed as you might be, that regret that you feel now will go away. If this guy was supposed to be your guy or soulmate or any of that stuff, you know,
Starting point is 00:30:08 you've seen enough of rom-coms where they've, you know, didn't, didn't shoot their shot a certain period of time, but it didn't matter when, as long as they shot their shot, that person came around. Right.
Starting point is 00:30:20 And so if he doesn't come around, I think the longterm, it'll be easier for you to stop thinking, you know, in terms of soulmate or regret or wishing you would have said something in the past and yada, yada, yada. So this is more of a personal exercise for you. And he'll have to decide what he wants to do, how he wants it. Does he tell his fiance? Does he not tell his fiance? Not really your problem. You know? Yeah. I forgot to also mention that I found out that he also cheated on her early on in their relationship with somebody else that I know. I mean, so do you want to change anything? Well, I mean, other than the fact that like, he's, you know, a cheater. Yeah. I mean, yeah, that is true. relationship is pretty solid. But also, I mean, of course it's a red flag. I mean, I've been cheated on a bunch of times and I wouldn't want to be in a relationship again where I have to worry about that. But I don't, I don't know if it's something that he would do over and over again. I mean,
Starting point is 00:31:34 I don't know. I think it may be just a low character moment. I don't know. I guess more hope. Well, the good news is if you guys, if you shoot your shot or not, you're not asking him to get engaged or get married. No. And then if he does surprise you and you guys start a relationship, I don't know on day one, you're like, oh, by the way, so I do know you cheated on her and let's get couple therapy. But I think
Starting point is 00:31:59 it could be something. I don't think you should ignore it. You can say, listen, I'm so happy we're here, but this did happen and i've been cheated on before and we all are imperfect people i've made mistakes but we have had so many close calls of losing this that i don't i want to do everything in our power to make sure we have the healthiest possible relationship would you be willing to go to couples therapy with me? Uh, can we talk about our past mistakes and past relationships and how well we don't want to do that to each other? You just, you communicate, you know, you just be open-minded to it. And, you know, again, if he
Starting point is 00:32:38 doesn't give you the reaction you want, you might learn that he's a douchebag, you know, or I don't know. So how are you going to plan on reaching out to this guy? I'll do it over text, but I have no idea what I would say. I kind of want to text him right now. Yeah. Right now? Oh my God. Should we write the text?
Starting point is 00:32:53 Right now? Let's do it. Okay, let's write it so at least I have it. Oh, if you write it, we're sending it. We're sending it? Oh my God. Okay. I think, okay, so maybe do we start by saying,
Starting point is 00:33:03 hi, I know that this is completely out of the blue and a very bold thing to do great but i saw that you were engaged and it's been messing with me if i'm being honest i think about you all the time i think about all the regrets i have with regards to our relationship yeah it wasn't really like a relationship i could still say that it was a relationship i you could still say that. It was a relationship. You could even say I have a lot of regrets when it comes to us. Yeah. There you go. Including
Starting point is 00:33:32 never fully giving us a shot. Never having the guts to put it all on the line for us. I completely understand if you don't feel the same way about me and if it's too late
Starting point is 00:33:47 I 100% respect that but I couldn't live with myself if I didn't tell you how I felt yeah there you go insert nude and then check out my body
Starting point is 00:34:04 do we definitely want to include i feel like nick you had a line something about like logistics like being like i'm ready uh yeah yeah so it's just like if you don't feel the same way you don't even owe me a response if you don't feel the same way but if there's any part of you that does, just know that I'm fully prepared to do whatever it takes to give us a real shot, give us a real shot at being in a relationship, giving us a real shot at being each other's person. I don't think you can go too hard to the pain here. She's sure you're literally trying to break up an engagement. Okay, true. If you think any of these things will rub him the wrong way,
Starting point is 00:34:45 he's not your guy. You really have to put yourself out there. Otherwise it is a bit fucked up for you to just like not really commit and dip your toes in the water and just be a distraction for him to want to like think, to think about someone else other than his fiance. No, you're a hundred percent right. That's true. I liked what you said before about, um, mentioning that this could kind of come off as disrespectful or like affecting other people's lives. Like I know it's selfish. Yeah, just be like, I understand this is... Yeah, don't we have a line that's like, I would never forgive myself or like, I couldn't do that. Like, I think you can couple it with that line being like, where you're like, if you not respond, like, I will fully respect your relationship. And I understand that this is a really selfish thing to do. Given the timing.
Starting point is 00:35:30 Given the timing and the way it impacts. And the way it impacts other people. Other people. I understand that this is a really selfish thing to do, given the timing. And the fact that it potentially impacts other people. I'm only doing this because i would never forgive myself for not saying something yeah it's a little repetitive i feel like yeah we can definitely we can edit yeah hi i know that this is completely out of the blue and a bold thing to do
Starting point is 00:35:55 but i saw that you got engaged and it's been messing with me if i'm being honest i think about you all the time i have a lot of regrets when it comes to us and the biggest is never having the guts to put it all on the line for us if you don't feel the same way and it's too late, you don't even owe me a response, and I 100% respect that. But I couldn't live with myself if I didn't let you know my true feelings. Just know that I'm fully prepared to do whatever it takes to be each other's person. I understand that this is a really selfish thing to do, given the timing and the fact that it potentially affects other people. I'm only doing this because I couldn't forgive myself for not saying anything. Boom! Solid. Is this how you feel? Yes. potentially affects other people. I'm only doing this because I couldn't forgive myself for not saying anything. All right.
Starting point is 00:36:26 Solid. Is this how you feel? Yes. But do you think like, I didn't put anything about like how I felt like we had this like insane chemistry and like no one's compared to you. It's implied. You literally just told him that you think about all him all the time and
Starting point is 00:36:40 you're willing to do anything to be each other's person. I feel like. Yeah, you're right. I don't know each other's person, I feel like... Yeah, you're right. I don't know if you need the sprinkles. Okay. All right. Okay, are you going to send it?
Starting point is 00:36:54 Do I have to send it right now? Yes. I think you should because I don't think you will. I think if you don't send this now, you're going to edit it. I want you to be confident that this is how you feel. And if this is how you feel, you can say that with 100% certainty, then there's no better time than now. Yeah, it's definitely how I feel. I if this is how you feel, you can say that with 100% certainty, then there's no better time than now. Yeah, it's definitely how I feel.
Starting point is 00:37:07 I'm just nervous of like embarrassing myself. This is not about whether, this is not about you embarrassing yourself or not. I think it's more embarrassing to live with regret. If he doesn't reply back the way you want, he's not your guy, right? And this is about you just getting it out of your system, so to speak.
Starting point is 00:37:23 You're putting it out there. You know, your ego, right? Your ego might say things like, well, just so you know, he's always going to know that he could have had you or that none of that matters, right? If he doesn't give you the answer you want, eventually, maybe six months from now, maybe two weeks from now, maybe three or four years from now, you're going to meet someone that makes you completely forget about this guy, or at least make you glad that he didn't give you the answer that you wanted.
Starting point is 00:37:51 It may not happen when you want it, but it will happen. Like, this is not about your ego. Your ego is the reason why you're in this mess in the first place, because you were too worried about being cool or not sounding crazy, wanting to be the chill girl or whatever it was. You weren't willing to put yourself out there and be vulnerable and just let someone know you care about them and put all your chips on the
Starting point is 00:38:16 table, willing to risk it all. And that's why you're in the mess that you're in now. So you got to change course. And this is more about closure than anything else. And it's a long shot that you're going to get the answer you want. But like we said before, this is already a selfish move. It would be 10 times more selfish for you to do anything less than this if you're going to put yourself out there. And you've already wasted enough time fantasizing about this guy or wishing you would have done things differently. You're wasting all this energy getting nowhere. So you might as well just go bold, put yourself out there, shoot your shot,
Starting point is 00:38:55 see if this is how he feels and let him deal with his mess. Let him deal with his decisions and his relationship and just make sure that you hold yourself and him accountable for not making the same mistakes that you made with each other in the past yeah you're 100 right i can't argue with that all right send it okay oh god just imagine there's a guy out there i've never met who's about to just be like holy shit i know yeah i bet his fucking fiance is gonna call in to ask nick oh my god what a dream what a dream three two one okay send it let's see it let's see it let's see it oh my god oh my god well we're obviously we need an update as soon as humanly possible. You did a very brave,
Starting point is 00:39:47 very bold thing. Thank you. Oh my God. Yeah. Congratulations. You, uh, you were vulnerable.
Starting point is 00:39:54 You put yourself out there. Now you just have to let the chips fall where they may. Do you feel at least a little bit good? How do you feel? Like, yeah, it's definitely, it's definitely a weight off my chest.
Starting point is 00:40:03 I've been thinking about it. Aren't you glad he knows how you feel? Yeah am i feel like if i feel that strongly like he should at least know yeah totally myself yeah yeah yeah god and yeah we don't know if he's your soulmate and we don't know if he's your person and we don't know if you could even be in like a good boyfriend or girlfriend situation we just know how you feel right now. We know that you've held on to these feelings in the past out of fear of looking silly. You've given in to your ego in the past. This is all about you not doing that now.
Starting point is 00:40:36 And he's going to deal with his shit or not. Right now, you need to feel good about what you just did and just being honest with yourself and communicating your feelings. And that hopefully should make you feel empowered regardless if you never hear from him because you even said, Hey, I'm not even expecting a response. No, I'm not.
Starting point is 00:40:55 Yeah. But that's true. Thank you. It was a, it was hard to do. Most people like this. Yeah. And like,
Starting point is 00:41:01 you're going to remember this moment for the rest of your life. You're going to, no, seriously, you know, and you, you are going to to i did this once a long time ago really yeah and i knew nothing happened you know right she didn't answer she did but it didn't go anywhere right and ultimately like they were never my soulmate and whatever but i just knew that i never did that and i knew that i just wanted to do that but i am my point of bringing that up is it took guts to do and i'm
Starting point is 00:41:32 glad i did it i'm proud of myself for doing that because i know that was hard to do and it has nothing really to do with her or anything like that yeah that's a good point. Okay. Alrighty. All right. Well, take care. Keep us posted. Thank you so much. Can't wait to find out. We're very excited. I don't want to give you false hope, but I will be shocked if he doesn't reply. You think? I hope he says something, even if he turns me down. It's too... Yeah, I just... He's not going to not reply. Because you laid it all out there and you were honest and you weren't
Starting point is 00:42:07 assuming anything. And yeah. Yeah, you're right. Unless, unless he feels guilty about, you know, cheating on his now fiance with you.
Starting point is 00:42:19 And true in a weird way, him not replying shows that he's maybe grown up a little bit. Yeah, that's a good point too. And if he does reply and not give you the answer you want, you can use that as like, because he shouldn't. He should not reply to you if he doesn't feel the same way about you. Right.
Starting point is 00:42:40 There's really, I guess, not much to say if he doesn't feel the same way. And the person I wrote, like I knew they would. there's really I guess not much to say if he doesn't feel and the person I wrote like I knew they would and I I I took that as knowing that she needed to like write me back because there was something you know because you know it had all the things she might even called me oh wow yeah but she shouldn't have she had no business replying to me and calling me. Yeah, that's a good point. She was in a very serious relationship at the time, you know, and she had no business doing that. So did she just call you to say that she didn't, like, didn't feel the same way
Starting point is 00:43:14 or didn't want to give it another shot? It was just more like, I just, it was, you know, she had her ways of doing things, so to speak. But yeah, it was just kind of like, I just wanted to acknowledge, I didn't want to ignore your message. But the truth is, he is engaged to this woman
Starting point is 00:43:33 and he did fuck up with you. And if he knows that he wants to be with her and regrets what he did with you, which has nothing to do with your value, your worth, or what he means to you, he should regrets what he did with you, which has nothing to do with your value, your worth, or what he means to you, he should regret what he did with you. And if he really wants to be with her, he has no business responding to you whatsoever. And so if he does respond to you in any way, shape, or form only to then reject you, that's shady. Yeah, you're right. I didn't think of it like that. It's, you know, he's doing it
Starting point is 00:44:05 because he kind of wants, he just wants to hear one more time how much, like, wants to hear your voice and it's an excuse to reach out. And he just doesn't have the guts to like do something as messy as end an engagement and it just all seems too complicated
Starting point is 00:44:20 and whatever. Yeah. But he should not reply to you unless he's willing to like you know fight for fight fight for you you know and he's willing to like leave you know all the more reason like you did the right thing and if you hear nothing that's just you letting it out into the world and just kind of a cleanse if you will yeah definitely all right okay thank you so much all right We're excited to
Starting point is 00:44:46 hear what happens. Thank you. I just wanted to say I read your book like a month ago and I absolutely loved it and definitely recommend it to everybody. Well, that means a lot. Thank you so much. Vilefiles.com. Of course. All right. Thank you so much. Take care. Okay. Bye. Bye. Bye. Hey, all you cookers out there. Have you checked out Caraway yet? If you haven't, you're nuts. But seriously, if you're looking for new pots and pans and baking ware, Caraway has it all, and it is excellent. I am an owner of two different Caraway sets, plus their cooking sheets. Just last week, we were cooking some potatoes, and we needed a cooking sheet for it. But we had some non-Caraway ones, like stuff built in the drawer, and I'm not allowed to even use those anymore.
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Starting point is 00:47:20 and so I understand the importance of grammar, and I panic so much before I send an email. The number of times I would reread emails before I had Grammarly, like I think about like years of my life were wasted doing that. For a million dollars, I could reread an email a million times and still not catch all the mistakes. And Grammarly catches all the mistakes. It also helps you strengthen your tone, which I think has been so powerful. Even things like saying, I think sometimes Grammarly will be like, you don't need to say that. And so it has these awesome, helpful recommendations to ensure that you're communicating in a very clear, concise, professional manner. I wish I would have had Grammarly go in college because I feel like there were so many Saturdays when you would have to write an essay and you kind of knew what you wanted to say, but you just couldn't get the wording out or you wanted to rephrase something later in a paper. And I just remember sitting and staring at a blank page of paper. And if I would have had a tool like that to just help me
Starting point is 00:48:12 like regenerate thoughts or just help me avoid writer's block, oh, the time I would have saved. A man and I are living proof that like we're, you know, you can be a dumb, dumb in the email, but like not, not that dumb in life. So stop looking dumb. Go ahead, be smart, do something smart today and get Grammarly. Go to grammarly.com slash go to download and learn more about Grammarly Go. That's G-R-A-M-M-A-R-L-Y.com slash go, grammarly.com slash go. How's it going? Okay. I am Sabrina. I'm 22 and I need advice on breaking up with my boyfriend almost five years. Okay. All right. So you're 22, five years, obviously first love. Yeah. Okay. Does he see it coming? No. At all. Okay. Like we've had talks, but I feel like I always like just push, I'm a pushover. And then like
Starting point is 00:49:09 we argue and then nothing gets resolved. And then we just move on. When you say you've had talks, what do you mean? Well, it's like the main reason that has sparked this all is that he refuses to come to my co-worker's wedding with me because he won't know anyone there is the only reason. And it comes up a lot that he won't want to come to the things that I'm doing. Like, whether it be like my best friend's birthday dinner or a family event. And I'm always upset about those things. And then he just says like, like selfish things like well why should i have to go and then i get mad and then like he just says like stubborn things like break up with me then
Starting point is 00:49:52 okay and then i never do okay all right what else why else do you want to break up though i'm not saying that's not he sounds like a dick yeah we hate him um okay but i just i i just i need i want there to be more for you because i don't want you to break up with him with this narrative in your head that i'm breaking up with him because he won't go to my friend's wedding because that's such that's such an easy fix for him to do to get out of jail so so to speak. And I am guessing that there are bigger, more deep rooted issues in this relationship. And if you're going to break up with them after five years, I want you to do it with conviction about your choice.
Starting point is 00:50:38 And listen, you're going to go through periods of sadness and loneliness, maybe even thoughts of regret of your decision. But you've been dating this guy for five years, you know who he is and, um, it's going to be a challenge for you to leave that relationship. It's going to be very easy for both of you to continue to hook up, um, and hang out and find your way back to each other. And this five-year relationship could turn into like a two-year breakup if you're not careful. Yeah. And I have thought about that too, because I'm like, oh, well he could, what if he says, um, I'll, I'll change everything. Like I'll
Starting point is 00:51:18 start coming to things with you. And I, I have like backup. I'm thinking at least because it's deeper rooted than that for me like um it's more that he doesn't care about what I'm interested in okay and he doesn't make any attempts to care he only cares about what he wants to care about and what benefits him and like obviously listen to listening to podcasts like this one i have a reference point of how i should be treated like he would never pump my gas for me even if i asked him to go that's all i needed to hear okay yeah and i don't think that even if he says i'll change everything like i think it's too deep of an easy fix. It's fundamental, but I'm scared that he will say that. Scared why? He almost certainly will.
Starting point is 00:52:15 He's very stubborn. I'm thinking he's going to say, I'll be like, okay, if you don't want me like this, then that's that. And then I'm going to be left like, oh, that is it after five years. Say that again. Well, like if I just say all these things about why I'm not feeling good about it, he's going to say, okay, well, if you don't like me how I am, then like, you can leave me then. And then I'm going to be like, I'm going to be the heartbroken one after five years that he won't even try to fight for me you're you're gonna be just kind of toxic yeah we're
Starting point is 00:52:49 all a little toxic um you're gonna be sad i mean you care i'm like if you if you're if you're both not sad then there's something else going on with you guys you know yeah this guy was you're you're 22 years old you've known this guy you've been in a relation with him for a quarter of your life that that's huge right so like we can't discount that you're you should be sad this should be difficult it doesn't matter if you're leaving or his leave he's leaving i don't know how he's going to handle it um be careful not to um critique um yeah his reactions in real time so to speak, because you're right, his first reaction might be defensiveness,
Starting point is 00:53:28 pride, his pride might take over. Fuck you, I don't care, just leave. In hopes that some kind of, it's manipulative, in hopes that you would then second guess yourself and say, no, just kidding, right? But if you show the conviction that you want to have, we have no idea. He is not, you, you just, you described yourself moments ago as a pushover. Right. So if you feel that way about yourself, chances are deep down, he feels that way about
Starting point is 00:53:55 you too. You know, whether he's going to say it or not, he treats you like you're a pushover. He is daring you to break up with him. Right. Yeah. And I don't. Yeah. Because I always stay. Yeah. So we're talking about a scenario in which you will stop being the pushover that he thinks you are. And when he meets that person, we have no idea how he's going to react to that because that will be a whole new you and that will throw him for a loop. And the moment he realizes he no longer
Starting point is 00:54:25 has the power that he now feels like he has over you then all bets are off in terms of predicting what he is going to do after that yeah yeah what matters is not none of that matters as far as you're concerned and your decision to want to break up with him you know and just you know like you don't need a reason to break up with him. He doesn't own you. I don't care if you break up with him for no reason. Be like, I don't know. I just don't want to.
Starting point is 00:54:53 I want you to have a reason for yourself because I want you to have conviction in your decision. So I want you to believe in your decision to leave him in this relationship. Again, we don't know what he's going to do, but whatever he does, is this going to be a reaction to your decision? So a
Starting point is 00:55:12 reaction to your initial, like, I think we should break up, then a possible reaction to the fact that you don't give in and that it sure comes across as that you're going to follow through with this threat because it's not going to be a threat.
Starting point is 00:55:25 He's going to see it as a threat at first. And then you realize it's not a threat, but actually something you're doing, then he's going to react, react a new way. But his reactions don't matter. You know, they're going to matter.
Starting point is 00:55:38 You've acknowledged that they might matter to your ego, but they, this is a relationship you want to leave. So that's a relationship that you want to end so i don't know why it's like human nature for us to like evaluate the meaning of a relationship that ends logically it's it makes no sense why does it have to have meaning it can have meaning for you right meaning in terms of like no matter what this guy was your first love and he will always be a memory for you he will be a significant one at first it's going to be super fucking weird for the next year you know he's the only one you've made out with i mean
Starting point is 00:56:15 is it have you slept with anyone else yes okay good for you um bravo well you know who knows like these are all like challenges, you know, you're familiar with him. So there's a lot of new things are going to, you know, it's going to be scary and uncomfortable for you, you know, um, folk, you know, and you're going to want to focus your energy on, on that, on you, on just getting you out of your comfort zone, trying new things. You don't want to waste any of your energy because that is energy. It takes energy worrying about how he's reacting to your decision. It takes energy thinking about whether he misses you or not. It takes energy wondering how regretful he is over losing you. And that takes energy. And that's energy you won't have on actually you moving forward.
Starting point is 00:57:06 Anytime you are wondering about him, you are still mentally in that relationship. And so many of us will say we're broken up or leave a relationship that we tell ourselves isn't healthy, but mentally stay in that relationship. And as long as we're mentally there, whether we're checking their Instagram or talking to our friends about them and wondering if they miss us and yada yada, we are emotionally and mentally still invested in that relationship. And while by title, he might not be your boyfriend, you're still very much in it. And that's what I want to make sure you don't do if you decide to leave yeah i feel like i'm very stuck on like making sure it's like
Starting point is 00:57:52 the perfect breakup which and it's hard for me to get past that because i'm like i know that my decision is right and like i'm not being treated well so i have to do this but then i'm thinking too much about like how he's going to react and he's going to react shitty totally shitty yeah this does not sound like you have not described someone who's going to be like you know what we had a good run i'll always love you let me know if you need anything i'll be your best friend no he's going that's the dream but is it though honestly that makes it more complicated. Let him hate you for a while. Let him talk some shit. Let him get angry.
Starting point is 00:58:28 His anger is a reflection of his love in a toxic way. He'll pretend to maybe be indifferent at first. Clearly he's not. Even if he is, that just shows you that if he acts indifferent, that's just a sign that you made the right decision. If you want to get angry at anyone, don't get angry at him. Get angry at yourself for staying in a relationship that probably deep down just a sign that you made the right decision it's a sign you know if you want to get angry at anyone don't get angry at him get angry at yourself or staying in a relationship that probably deep down you know that you stayed in longer than you should have and there's no sense in beating yourself up over that emotionally but that should challenge you to like not waste
Starting point is 00:58:57 any more time than you've already wasted yeah so how do we want to tell them i'm i don't know i've never had to do it before oh i've considered being like one of these days someone's gonna ask you to break up with their boyfriend no because i genuinely think it comes across as kind of a joke but nick means it out of like the goodness of his heart because i've like cried to nick before about how stressed i was to do it and he was like do you want me to do it? And I was like, what a tender moment that was. Do you live together? No. We live with our parents, but we spend every night together, whether it be at his house or mine. So I've been there.
Starting point is 00:59:33 Either at his parents or yours? Either. I'm at his house right now. Right now? Not right now. Currently, I'm sleeping there at night. Okay. I mean, you could just slow play it. pack your bags, whatever bags that you have at his place. I've been slowly bringing things home. And then just hit him a text saying, hey, I just been busy. Be vague. I'm going to stay at my parents' house for now. For now. I love that. Say for now. I don't want him to know that I have known that I'm going to do this for a week now.
Starting point is 01:00:08 That's why I feel like I have to bring up the wedding. Why? I mean, why? It doesn't really matter, but why? It kind of just to spark the argument so I can be like, I'm leaving. The alternative is that you woke up one day and just arbitrarily decided to dump him, which that's not... Yes. It makes sense that you would put some thought into ending a five-year relationship. There's nothing wrong with that.
Starting point is 01:00:32 Yes. I've been thinking a lot about this. You've been the most important person in my life for five years. I'm not happy. I don't like the way you treat me. I don't like the way that you literally threaten to break up with me. You make me feel bad for having expectations of you. You make me feel like I'm doing something wrong by wanting you to like show an interest in the things that I'm
Starting point is 01:00:58 interested in. I don't feel like you're willing to do the same things that I'm willing to do for you. And there's a pattern here. I need to copy paste that. I can repeat it. Into my brain. But write this down. You think of, you know, I'm essentially just repeating back what you told me. Are you willing to do this in person?
Starting point is 01:01:19 I don't think you have to. Oh, yeah. I'm doing it in person for sure. I don't want to. I mean, if I was, but that would just be very out of character for me to like send a Text where do you think you do this? At his house. I have all my friends on standby to pick me up because I don't think I'll be in a position to drive After maybe I will I have literally no idea how it's gonna go. I've never been in this situation before
Starting point is 01:01:43 So maybe I won't even cry i've cried enough this past week yeah who knows and who knows if he cries i would i would have no expectations of him because i know it's having expectations that wishes he did yeah oh that needs to leave expectations in these scenarios only leads to disappointment so yeah have no expectations his reactions are just going to be that just they're going to be reactions of him being shocked and surprised and not emotionally regulated and caught off guard and upset and triggered none of them are really reflections of how he feels about you or the relationship. And none of that really matters. Also on the flip side, if you have no expectations
Starting point is 01:02:34 and let's say that he out of nowhere handles it super well and seems very receptive, I think it's easy to misinterpret like, oh, thank God this conversation was over. He handled it so well. Maybe I made a mistake. Maybe it's whatever. It's so easy to jump back into your head because you're so glad that the anxiety you've been feeling this past week is over. But don't confuse that with this being a great relationship and it being perfect and you forgetting about all the issues that have been popping up. Yeah, I'm not too worried about that happening because if he takes it well, I'm assuming you'll be bummed that he's not sad. I think it will.
Starting point is 01:03:07 And if he takes it hard, you'll feel guilty and wondering if you're being too harsh or mean, you know. So either way, you're probably going to feel shitty. I have a list in my phone of like, if I do regret it later, I have to look back at all these reasons why I did it. So like, I don't feel regret. And I know that even if he thinks I was wrong in my choices and thinks that I'm expecting too much, I know that I like even if he thinks I was wrong in my choices and thinks that I'm expecting too much I know that like I'm not wrong that's so smart and I also think like when you're like really hurting it's like one of the times you're most connected to yourself and it's like kind of like a weird like bitter so you're like oh fuck I can't be very connected
Starting point is 01:03:38 when I'm extremely happy like no that's not how this works but like you know if it feels like shit you're doing it right and I just I think it's so easy to want to do things that like perfectly and like really as cheesy as it sounds like doing your best and like really making sure you're holding yourself to your best not some version of reality where like you can pick and choose from like a bunch of different reactions and say a bunch of different things like you know like it's just it's like it's inherently messy and shitty and so as long as like you truly believe that like you are doing your best you're doing everything you can and like extricating yourself from the situation and then you let yourself like sit in the shit for a few days like or you know longer than a few days
Starting point is 01:04:18 probably but like it will i feel like it will really pay dividends and i think you'll look back on this as like a time that was like whoa i became a new person on the other side of this how confident are you in in your decision to do this and how and how determined are you are you to do it i'm very confident my decision like 100 confident in my decision the more that i like tell a friend or i've already told my parents and like as soon as i actually opened up to my friends and family they were like yeah like we've been seeing this. And then like, no one has told me like, you're wrong. You know, everyone has been like, yep.
Starting point is 01:04:49 It would not shock me if he comes crying back at some point. Yeah, that's what most people have also said. That's his loss. I mean, this should be a wake up for him. It's not your problem. And even if he does, it was way too late. problem and even if he does it was way too late he needs to realize you're gone gone gone gone with someone else before he was before he will actually realize the full mistake that he made and actually want to make changes and and be a better partner to someone else in the future
Starting point is 01:05:20 because he lost out on you simply waiting a week and then regretting, oh, I'm so sorry, I'll do this. Those are just reactions and they will quickly go away once he gets you back. That's like, at first when I was thinking about doing this, I was like, well, maybe he can work towards it. But then I was like, it's too, It's not a one-day fix. It's not even a week fix. It's real deep-down fixes that he would need to do. Yeah. I'm sure he wouldn't even entertain couples therapy. No.
Starting point is 01:05:56 He thinks it's crazy. I have a therapist. That's a red flag for sure. Yeah. Well, just another thing to add to the list. I know it sounds crazy, but I have like set a date, like,
Starting point is 01:06:07 which is like the next best possible opportunity because like we both are working two jobs and it's golf season. I just need you to get, I need you to get it out of your head. This whole like goal of some sort of clean, beautiful breakup. Yeah. Doesn't exist.
Starting point is 01:06:24 And honestly, I don't think you want that. It's more confusing than you realize. Like some sort of like amicable breakup. Like what is that? That is a recipe for wasting way more time. And romanticizing the shit out of that. Yeah, and having me hard. Because you will, no matter how shitty he was,
Starting point is 01:06:40 he was a big part of your life. And like, you're gonna, it's more likely than that you will feel lonely you're gonna miss him you're gonna miss that comfortability if nothing else and and when you get back there and start dating like spoiler there's a lot of other shitty guys out there so you're gonna have more bad dates than good dates right that doesn't mean that oh you know if you go on, if your first three dates are with guys who are more rude or more inconsiderate than him, that does not a reflection
Starting point is 01:07:12 or it does not mean that you made a mistake or that you weren't as grateful for what you had. It just unfortunately means this is a lot of shitty guys out there. And you are, might have, you might have to go on 5, 10, 15, 20, 25 dates, 30 dates I don't know, over the next 2-3 years, you are only 22? You're only 22, I don't know how that feels to you
Starting point is 01:07:35 but you know, I'm here to say it's pretty fucking young and you could easily be single for the next 2-3 years and date around and get to know. And that's what honestly I would encourage you. I mean, if you're lucky enough to meet someone you really want to settle down with, great, you know, or get in a relationship.
Starting point is 01:07:52 But you've been dating one guy for your entire adult life. And I think it's time to learn about who else is out there, you know, and you can do that with intention. You can do that, you know, while participating do that with intention. You can do that, you know, while participating in hookup culture, you can do that without participating in hookup culture. You have a lot of variety. I think you should just focus on meeting people, making friends, learning about new, you know, personalities, get to know different guys, you know, strike up friendships with men, you know, and things like that. Take it slow and
Starting point is 01:08:23 enjoy doing that rather than trying to replace him. People make the mistake of leaving a relationship and they feel this like, you know, they feel a literal void. I mean, whatever you did with, you know, you're no longer going to be going to his parents' house. So all your routines that you have are going to be gone and those are going to be spaced. Those are going to, they're going to feel like actual voids that you're going to kind of have anxiety about filling. So you don't have to do that all that once. And
Starting point is 01:08:51 you certainly don't have to do that with a romantic partner. You can do that with friends and dates and things like that. So just kind of prepare yourself for all that because too many of us kind of don't prepare ourselves and then we panic and then we resort back to the thing that we spent so much energy trying to leave. I feel like this was super helpful for me. I really want to break up with him. I just have to take the leap. Yeah. Well, we can't wait to hear about how it goes.
Starting point is 01:09:17 Please, we will book you for a follow-up as soon as possible. Talk through it. And you're doing something really brave. It's okay that he hates you for a period of time. Yeah. It's just hard. I know. And honestly, that's just a reaction.
Starting point is 01:09:35 But get it out of your head that you're trying to cultivate some perfect breakup. He can be angry at you. Hopefully, he doesn't say anything, you know. Mean. He's going to say something mean. hopefully in any he'll be angry and hurt and on you know he has the right to be angry and hurt you know and i'm sure whatever he says will feel mean hopefully it's isn't crossing any you know serious lines but regardless you know all the more validation you have but he has the right to be angry he has the right to be caught off guard and sad. He has a right to feel emotion and hopefully he's, you know, operates within certain parameters of, of right and wrong, but just prepare
Starting point is 01:10:18 yourself and tell yourself it is okay for him to treat me like the bad guy because in your world he is you know but that doesn't mean you are just kind of prepare yourself for that and it's okay for him to see you that way because that's that's what that's expected you know he yeah he part of the reason you're doing this is because it he doesn't get it you're not on the same page. You don't see relationships the same way. So you should expect to be disappointed with his reaction. All right. Well, good luck. The fact that you're so confident clearly means you're making the right decision. It's going to be exciting. This is going to be really great for you. I think so too. It's just the actually doing it that is like in the way.
Starting point is 01:11:08 Do you have any boys out there that you've laid your eyes on? Okay. No fun. No, I'm not saying you were like emotionally cheating or anything like that, but like, you know, listen,
Starting point is 01:11:19 like after five years of being emotionally beat down, like you tend to be like, wow, that guy looks nice. You know? Yeah. Wow. After five years of being emotionally beat down, you tend to be like, wow, that guy looks nice. Yeah. Wow, that guy looks nice. I don't know. This is the most like... You just get tired of...
Starting point is 01:11:34 Yeah, you just see that things look more appetizing. Man, he gets my pantaloons wet. But if I were you, I would just go have fun with friends for the night time being. Totally. That's the plan. They all know.
Starting point is 01:11:46 So they're like fully readied. Like they're going to be at my house all week. This is their super boy. Summer's coming up. Hot girl summer. Hot girl summer. We love that. And also this is like if you were watching a movie about yourself and then you did this thing, you'd be like, oh, fuck.
Starting point is 01:12:02 Wait, I kind of underestimated this character. I thought she was just like kind of people pleaser like you know those points when you're watching a movie and then they a character does something you're like oh shit they have more to them than i thought this is what you're doing for yourself and it's real life i never thought that i could do this like i was like oh i'll just settle this is good enough and then like i'm like oh i'm only 22 yeah i can't put up with this shit. Yeah. The rest of your life. Yeah. Yeah.
Starting point is 01:12:27 Yeah. Yeah. Single. I think it's important to be single for a while, at least. Definitely. I'm not looking to move on like that kind of move on yet. Obviously. There's no wrong way to move on.
Starting point is 01:12:41 Who knows? No. Be open-minded. Everyone's different. Be open-minded. I'm so be open-minded i'm more interested in trying new things because he would never do that with me sounds like a ball of fun yeah right why does he want to go to a wedding yeah he says he won't know anyone there he's with you enough fun yeah oh he says things like well if my friend was there
Starting point is 01:13:05 i would have fun and that was like when it really clicked though i was like he's my best friend i'm not his best friend there you go boy bye all right well keep us posted i'm excited for you i can't wait yeah thanks i know i know you're like bumming it but i wish i'm excited like i am excited to move forward it's the like the hard part of actually having the conversation. I'm just like envious of you that you get to break up with someone, you know. What is up with you and breakups recently? Because you guys all dread it so much and I don't give a shit. So, you know, like.
Starting point is 01:13:36 I'm for you. And these particular stories, it would just be fun to. Just rain on some shitty fuckboy braids. If I could have like you could be in my body and do it for me, that'd be great. Yeah. We'll be talking to you. I will email you. We'll be talking to you next week to get an update to hear about how it goes and how you're
Starting point is 01:13:50 feeling. Yeah. And you got this. And I love that your friends are so supportive and are going to pick you up and everything. Yeah. That's amazing. And it is absolutely what you deserve. All right.
Starting point is 01:13:58 Good luck. We're rooting for you. Godspeed. Thank you. All right. Take care. All right. All right.
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Starting point is 01:17:59 of $100 or more. What's going on? Hey, I'm Cheyenne. I'm 27 and I'm matched with my boss on Hinge. Nice to meet you, Cheyenne. Okay. Tell me more. So I had seen him on there. So to start at the beginning, I was interviewing for a job and he was one of the people I interviewed with. At the time, did not know he was going to be my boss and I clocked it. I was like, oh, cute. Amazing. Fast forward, got the job. He got promoted and I found out I was going to be on his team. I also found out during that interview, he had a girlfriend. It just came up in casual conversation on Valentine's day. He asked me what I was doing.
Starting point is 01:18:40 During the interview, you're like, that's a hottie. I'd like to see him naked. Yes. That was things that like, while you're trying to get a hottie i'd like to see him naked yes that's that was things that like while you're trying to get the job immediately clocked it immediately like i wonder how big his dick is yeah okay is that something women would think about honest question well i'll let cheyenne answer for herself because like what do you guys like you know men are pervy you know uh we're weird we think about all different things You see a guy you find sorry I'm going on a tangent
Starting point is 01:19:08 Here I know this is your time You see a guy Like his face you like his shoulders At any point are you Like wondering how big his dick is I don't feel like I jump straight to dick Not immediately At what point is it something that's
Starting point is 01:19:24 On your radar if we're like making out and starting to get handsy okay like it's not really something that like crosses so really not until you're holding it do you even have an opinion of it yeah yeah interesting okay yeah something new every day all right so anyways you're fantasizing about his dick no yes of course. He has great hair. That's the first thing I noticed. Okay. He has great hair.
Starting point is 01:19:48 All right. So now you are reporting to him. You got the job. Yes. He got promoted. Oh, by the way, he's your boss. All right. Continue.
Starting point is 01:19:59 Yes. So one of my one-on-ones in the office, it was on Valentine's Day. I was single. I am single. So I didn't even clock that it was Valentineentine's day and he was like what are you doing tonight and i was like nothing um and he made he made a point to say that he was going to sing sad songs at a writer's round because he's single and i was like oh interesting to bring that up good luck whatever how old is this guy i'm 28 Okay. I've had some stuff going on personally. So I haven't been in the office too much. That has since resolved. Got back on the
Starting point is 01:20:33 apps. Saw him on Hinge. He was in my standout. So I was like, I feel like giving a rose is a little much. What does that mean for the people who don't know? Yeah. So Hinge picks people that they think you're interested in puts them in a special category and if you want to match with them you have to give them a rose i think they give you one and if you want more you have to buy more okay um so that's where he was and i was like okay single cute whatever like a week goes by he's back in my standouts and i was like okay interesting he also either didn't see me or didn't swipe no I'm gonna tell my ego he didn't swipe no
Starting point is 01:21:07 but again he's in my standouts so I was like Rose is too much last week he popped up in my normal batch of men and my therapy appointment got cancelled that morning so I
Starting point is 01:21:24 was like screw it so so i matched with him and i put a note there and i'm gonna match with my parents no parents my therapist would have told me no but whatever she got canceled hello um so i just made a comment about a show that he had quoted and then i also i gave him an out cause I definitely don't want to make him uncomfortable. So I just gave the out of like, I hope it's not as bad for you on here as it is for me. So that it was kind of like, you know, I didn't want to be direct and be like, like a friendly hello. Yeah. Yes. Well, I actually, yeah, I, um, when I was on, when I was single and on Raya, I, uh this because she tricked me down on her show to talk about it, but I saw Nikki Glaser on there. hey, I see you on here type of thing with the assumption that, well, clearly this is not a romantic thing because we're just friends. But I realized that I needed to be a little more careful
Starting point is 01:22:35 with that. So knowing that you guys matched, yeah. So it's interesting that you kind of had that foresight and threw it out there as a, hey, it's like two people, like on a lake where you drive past a boat and everyone waves, you know, like boat etiquette. It's kind of like you guys just kind of waving at each other on the app, so to speak. Right. And then what happened? I wanted to do that. Okay. And then what happened? So he responded back and quoted something from the same TV show. I quoted back and then he quoted back. I quoted back.
Starting point is 01:23:10 So now I was the last one to say something. So kind of where I'm at is like, I want to leave it at a place where I can say something that implies enough that I would be interested so that he could pick it up. But I also don't want to make this a weird dynamic and just outwardly be like, I want to go out with you or ask him on drinks because I definitely like, I don't want to make it uncomfortable for him. I don't want to make it uncomfortable for me.
Starting point is 01:23:35 So yeah, that's kind of where we're at. So has he replied to that? So we went back and forth, I think three or four times. And I was the last one that has sent a message. I need to read us all these messages okay oh yes so it's a show on netflix uh called i think you should leave so i quoted and said i auditioned for that show wait what that's very cool i love that show okay um so i said i knew you got your clothes at dan flashes hope it's not as bad for you out here as it is for me. And he said, everyone keeps eating the fully loaded nachos.
Starting point is 01:24:10 They have a rule, you know, in all caps. And then I was going to try to make it flirtier. And I said, have you seen the Tim Robinson episode of the characters? Want to make sure you're up to date before I start hurling quotes. And he said, pointer brothers, question mark. And I said, are you standing up or have you been pointed at today? Because that's the whole kind of gag of that skit. And that is where it has left off. Not much to go on. No.
Starting point is 01:24:32 And what is like the cadence of these messages? Like how much time is passing? So the first couple, when I matched with him, he matched within 11 minutes. So I don't know if I just caught him when he was on the app, but the last message I sent was... He certainly didn't think about it. Right. So the last message I sent was Sunday. I actually... And I had my one-on-one with him after this. So... Interesting. What? Okay. Okay. I know. Well, okay. For the obvious questions we need to ask, how much do you love this job? I mean, I like it, but if I it, but if this did progress and I had to get moved to a new team or anything like that, I would not be sad. How big is this company?
Starting point is 01:25:12 It's pretty big. Okay. It's pretty big. So they definitely have an HR and they definitely have a policy around this type of topic. Yes. I believe it would be... I cannot be with anyone that affects my performance or that I report to so it would definitely if this did happen would have to switch teams I feel like you've made the first move and I feel like you need
Starting point is 01:25:36 to sit back and wait for him to make the second move that's what I think a lot of banter your inside jokes these are all positive signs but he is your boss and i would rather have him take the risk than you right he's in a position of power literally over you he's your boss because like if you guys go on one day you guys gotta like and that's another question like. I don't know how you are and certainly I don't know anything about him, but if this is a
Starting point is 01:26:09 large company, I don't think you should go on a date and see how it goes to see if it's worth telling HR because you don't know how the date's going to go. The last thing you need is some rumor that gets to the wrong person and they're like, and then your coworkers, if they catch wind, you know, and then your coworkers, you know, if they catch wind that you're dating your guys' boss, you know, people gossip at work, you don't want to get a reputation, you don't want people to think, oh, well, you're getting special favoritisms or just because you went on one date, you know? So you have to ask yourself, is even going on a date with him worth drastically affecting
Starting point is 01:26:47 your job? I mean, I don't know how he is as a boss. How long have you worked there for? Just six months, less than that. Okay. But it's six months. So you have a rapport with him. Do you like him as a boss?
Starting point is 01:27:00 I do. I haven't had that much interaction, which I think is why I'm a little, I feel a little more separate from it just because I haven't been in the office. I've been basically work from home. I'm pretty self-sufficient. So I think that's why I'm not having like, even you're completely correct in what you're saying. I think it's just, it's not registering as much because I don't have that normal. And is the working from home, like, let's say, okay, you go on a date with this guy, you report to HR. They're like, okay, cool. Well, thanks for letting us know. He can't be
Starting point is 01:27:31 your boss anymore. We got to switch you to a team. Would you still be working from home, regardless of who your boss is? Yeah. Okay. Are you familiar with any of the other potential new bosses? Not fully, but there's a bunch of different teams and industries within the realm that I work in. And I know we are hiring. So I know that there are options. My biggest question, because I too got advice from my friends and had the thought process that he should probably make the move. But i was almost wondering if it's a bigger risk for him because it's like if if i make a move and he rejects me it's like oh this will be awkward but if the person in power makes the move and i reject it i feel like i have a pretty strong hr
Starting point is 01:28:18 case if that was the case so i think that was you're not gonna reject him no but i he doesn't know that he might that's the that was the back and forth in my head because i agree i would love him to make it but i don't know if he has more to lose if it goes awry than i do i mean yeah he for sure does yeah it's like it's tough because it's like there's you're at the kind of like the flirty banter like cat and mouse like I think we stigmatize game playing so much in dating and granted like there it's there's many ways that it's so unhealthy and shitty but there's also like the reason it exists at all is because it's like a fun like it's that chemistry and the way you get propelled so it's like hard being at that stage while also in a
Starting point is 01:29:04 kind of delicate situation that seems like it requires a lot of like communication but it also feels like if he was that concerned about hr he wouldn't have matched with you to begin with or he wouldn't be sending these messages back and forth yeah i mean not not everyone is me that's for sure but short of me being like you know what i don't this this person i'm obsessed i wouldn't i wouldn't even mess with it i would not have matched with you even if i would have thought you were cute even if you would have been someone that you know in a different situation i might be interested in going on a date because like why not no i would have to be super into it. I definitely think, listen, I definitely, the safe bet is to wait.
Starting point is 01:29:49 And I think there's things you can do in the meantime to like encourage him to take the risk. And you're one-on-one, you know, you could bring it up. Then like, yeah, it's tough out there, you know, or whatever. I guess whenever you have a chance, I think the line, the line of, I'm just waiting for the right person to ask me out could be good. I like that. So if he asks you about the app, yeah, it's been a bit slow. Honestly, I'm just waiting
Starting point is 01:30:13 for the right person to ask me out. Give him a little twinkle. Right. I am trying to subtly plug it. Yesterday, we were going back and forth about something that i had to do and he told me that my work was beautiful and i was like don't be too nice to me it'll go to my head just trying to like be a little bit more playful back and forth yeah you might have a little bit more direct than that yes i just didn't want it in writing no super smart yeah do that in person for sure do you think he's going to mention something okay so I'm assuming what if you're just like at some point at the end of the 101 you're like so hinge
Starting point is 01:30:50 that's a wild place that's what I was going to say are you going to acknowledge that at all like is this meeting recorded or is this just like a zoom between the two of you it's just a zoom and it's usually pretty light hearted because like I'm pretty well supported in my job function.
Starting point is 01:31:06 So I usually don't have that many questions to ask him. So we usually just talk about life. Like in our last one on one, we ended up talking about like tattoos and this new bar that was opening up. So it usually does end up being pretty lighthearted. So I feel like I could definitely just kind of bring it up and see see what he says. Yeah, just be like, so it's just of bring it up and see, see what he says. Yeah. Just be like, so a wild play, a casual fun way,
Starting point is 01:31:28 not a, I really want to just sit down with and talk with you about X, Y, and Z. Yeah. You just kind of, you literally just say the word hinge. I don't know if this would be too subtle,
Starting point is 01:31:36 but like referencing, I think you should leave. Could also be a gateway. Yeah. There's, there's a quote about like, I hope you don't have a bad time at work something like that that i was gonna work in in the future depending on how it went but i wanted
Starting point is 01:31:51 to get the experts advice first because this is this is my first foray into uh being attracted to the boss i think uh just kind of play around with it But whenever he asks you about how it's going for you, that's when you hit him with the, well, you know, it's been a little slow. Just like, I just been waiting for the right person to ask me out.
Starting point is 01:32:17 I like that. That's pretty fucking direct without giving anything away. Do you think I should definitely do this? Like keep it to the one-on-one and kind of leave the hinge messages alone for now uh well i i wouldn't yeah i wouldn't send him another message was he did he send the last one no it was me yeah yeah then we gotta leave it for now leave it for sure yeah this is this is helpful because i i try i don't i've never been in a relationship i don't i feel like i don't like people you've never been in a relationship i
Starting point is 01:32:52 mean i've been on dates and stuff it just never progressed so i find myself sometimes getting self-aware and over correcting to the point where i'm like do i actually like this person or is it just you know he's nice so sometimes I feel like I overcorrect. Well, you know, but why do you, like when you say you've never been in a relationship, what's the longest interaction with, uh, someone you've dated you've had? Um, two or three months. Okay. And then what happened? Um, well, that one was when I was 22. We were together. I just jumped in it way too
Starting point is 01:33:25 fast because I think I was excited. Someone wanted me to be their girlfriend. And then we got into it and I was like, oh, this is not it. So I broke it off. But no, I mean, nothing major has ever happened. I feel like I'm in a much better place in my life now going to therapy and having gone to therapy for a lot longer to understand what I want. But I think I was just, I would get to a place where it would start to go well and I would self-sabotage. So. Okay. Well, good for you for being in therapy. Yeah. I wouldn't think too much about the never had a boyfriend type of thing. You've been out there, you've been dating, you have experience. Yeah. I i would but i think the next move is definitely on him both on the apps and you know all you can do is continue to kind of give him the
Starting point is 01:34:10 as many non-verbal green lights as possible right but i also yeah but i also would just be willing to like let it go absolutely yeah like it might be nice to really try to go on a date in the next week or like week and a half with somebody else just so that way like you don't have to be like super reactive about it. Like I can't think about him. And it seems like you're in a really good headspace. You're like kind of intrigued and you're like interested. And like for me, I know when I'm in that headspace, I can either like maintain it or I can go off the deep end and get very invested. maintain it or i can go off the deep end and get very invested and so i think like having another like pot on the burner so to speak just to kind of take some of your attention away so he's not monopolizing it accidentally it could be helpful provide perspective i'm you know the more i think about it too like this guy is your boss i would just slow play this what you know there's what's what's the rush?
Starting point is 01:35:06 He's not going anywhere. Exactly. I mean, who knows? I guess he could quit tomorrow. Well, listen, if he quits his job, then you could ask him out immediately. So there's that. Right.
Starting point is 01:35:19 But assuming he continues to be your boss for a period of time, or you guys continue to work at the same company, he's not going anywhere. And I guess he could find a girlfriend or not, but if that's the case, then so be it. Yeah. But in the meantime, I think you want to be mindful of kind of the energy you give out to him.
Starting point is 01:35:41 So be careful about complaining about dating around him i want you to give off the impression of highly successful dater be very confident and have a level of mystery that you're very desired and and things like that you know you don't have to really even say anything but just kind of the energy you want to give off to him um and let him if he is thinking about you let him continue to think about you let him wonder about you let him you know let him ask you questions about your personal life and be be open to being not super open at first you know you can be a little cagey and a little yeah you know flirtatious that way because that's you don't want correct me if i'm wrong but i'm assuming you don't want to go on a date with them
Starting point is 01:36:31 fuck and then have like you know i don't you don't want this to be like a fuck boy situation or just a random hookup no because like what's that that's not worth it right so while you guys work together use this as an opportunity to actually get to know him more because you don't really know him that well so if i'm him if i'm interested in you at all you know i don't just let's say i just think you're attractive you know if i'm thinking about asking you out i'm just doing nothing for a while and I'm just getting to know you. And I'm seeing if there's something to build there. You can almost date without dating, if that makes sense. Maybe that's a reason to get into... Can you go into the office a little more often?
Starting point is 01:37:20 Yeah, absolutely. So there's that. You can play with that. So yeah, I would definitely not make any moves and just focus on getting to know the guy. Ask him questions. See what he's willing to give you. Nothing. And yeah, honestly, I think that's what you do. Not that I'm more I'm thinking about it. I think you do less to try to get to that question.
Starting point is 01:37:44 I mean, listen, if he sets it up, you can always say it, right? But I wouldn't force it. For the time being, I would just get to know him. He's only been your boss for six months. You haven't really spent a lot of time with him. Most of your time at this company has been working from home. You've had a couple of one-on-ones, et cetera, et cetera. You've talked to him maybe even more on the dating apps than you have at work. So change that. You have access to him, you know? And so you can utilize that access
Starting point is 01:38:11 by getting to know this guy, getting familiar with him, getting to know his jokes, you know, talk about stuff, have that kind of office boyfriend, if you will, without, you know, and just be careful about, you you know how people don't be flirty around it be very careful about your surroundings um even when you are just hanging out with them uh at work um and yeah i think you can get a lot more information about one another so that if you guys do decide to do something you're doing it with a lot more information you have right now because right now i honestly think it with a lot more information than you have right now. Because right now, I honestly think it's pretty risky for both of you
Starting point is 01:38:47 to just be like, hey, do you want to go on a date? And it's kind of nuts when you think about it. To have almost no rapport, match on a dating app, you like his hair, he likes your face, and you guys are willing to go to HR and completely change bosses
Starting point is 01:39:03 just because someone you think is cute. Yeah. That's, that's not very reasonable. So I, I would, I would invest more time on just getting to know each other and seeing if there's chemistry and a connection and a familiarity where you're at the
Starting point is 01:39:19 point of, you really know each other, you become friends and coworkers and that passion, that desire is there. And if you guys end up going on a date, you're definitely going to be fucking on the first night, but only after you guys both mutually decide that this is worth it. Yeah. I think that's a great point. That's something that I'm telling myself too, is I don't know him. I like what I see. I like what I know, but I don't know him like i like what i see i like what i know but i don't know him so to like obvious like you're saying to throw this all away potentially for nothing i definitely
Starting point is 01:39:51 don't want to do and i do i was supposed to go on a date yesterday but i found out the guy um i'm in a dating support group and he apparently has a record and has undisclosed std so i canceled that um but i am trying to like stay active uh so in the city it's like for women this one is for women uh to post about men that they've had bad experiences with some of them are legitimate some of them are oh he texted me in a tone i didn't like so i try to take it with a grain of salt but there's definitely some legitimate red flags in there so I'm really glad I trusted my gut and checked but yeah
Starting point is 01:40:31 I've seen them before like people will post you know anyone who's potentially concerning it's like a Facebook group yeah helpful to an extent you could definitely get lost in there with people that are just like oh he ghosted me which I don't think is reason enough to write a whole human off. But there are some legitimate concerns. But yeah, trying to keep myself busy, go on dates, not put
Starting point is 01:40:54 all my eggs in this basket. But I recognize my downfall is I need to take it slow, let it go, and almost kind of just slow play it. Yeah. I would just get to know him, you know, see if there's actually some reporter there, some chemistry. Yeah. Because at this point I could go on a date with him, hate him, and then we've blown up our lives for nothing. Correct. All right. Well, it sounds like we have a plan. Awesome. We do. I appreciate it. Thank you guys so much for having me on. Oh, I will. If there's any update, we would love to hear it. I will. I'll let you know.
Starting point is 01:41:30 I don't think this one-on-one will probably won't be too juicy, but if anything comes up, I'll definitely keep you guys posted. For sure. Yeah. But come in with a couple of like, just questions about like, Hey, how's, how's life? You know, watching you. What are you binging? What are you watching? You know?
Starting point is 01:41:42 Yeah. All right. We're excited for an update. Good luck. Absolutely. Thank you guys so much. Thank you for your time. Take care. We're excited for an update. Good luck. Absolutely. Thank you guys so much. Thank you for your time. Take care.
Starting point is 01:41:48 Thanks. Take care. Thanks. Bye-bye. Take care. Bye. Thanks for listening, guys. Don't forget to check out Vile Files Plus for your update special that dropped last Friday.
Starting point is 01:42:01 Get ready for an amazing week. We'll see you back tomorrow. Bye.

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