The Viall Files - E1094 Ask Nick - I Like My Coworker… But I'm HR
Episode Date: March 16, 2026Our first caller has developed a massive crush on her coworker and is ready to shoot her shot, except she works in HR. Our second caller is dating a genuinely great guy, stable, kind, everything on he...r checklist, and she feels absolutely nothing. So what does that mean? And our third caller is done swiping and getting nowhere. She wants to know if she's the problem or if the apps are just completely broken. "You can't have high standards and like everybody." Listen to Humble Brag with Cynthia Bailey and Crystal Kung Minkoff every Monday. Available wherever you get your podcasts and YouTube: https://www.youtube.com/@humblebragpod https://podcasts.apple.com/us/podcast/humble-brag-with-crystal-and-cynthia/id1774286896 https://open.spotify.com/show/4NWA8LBk15l2u5tNQqDcOO?si=c03a23d537f94735 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. To Order Nick's Book Go To: https://www.viallfiles.com If you would like to get some texting advice, send an email to asknick@theviallfiles.com with "Texting Office Hours" in the subject line! To advertise on this podcast please email: ad-sales@libsyn.com or go to: https://advertising.libsyn.com/theviallfiles THANK YOU TO OUR SPONSORS: Coop - Let Coop help you show up feeling rejuvenated and ready to go. Get 20% off your first order and try Coop risk-free with a 100-night sleep-better guarantee at https://coopsleepgoods.com/viall . Ritual - Don't settle for less than evidence-based support. Save 25% on your first month at https://Ritual.com/viall Neuro Gum - You can find Neuro at CVS, Amazon, and at https://NeuroGum.com. For a limited time, you can get 20% off your first order at NeuroGum.com by using code: VIALL Article - Article is offering our listeners $50 off your first purchase of $100 or more. To claim, visit https://article.com/viall and the discount will be automatically applied at checkout ASPCA - To explore coverage, visit https://aspcapetinsurance.com/viall Eligibility restrictions apply. Visit https://aspcapetinsurance.com/amazonterms for more info. Timestamps: 00:00 - Intro 00:54 - Caller One17:16 - Caller Two 32:36 - Caller Three Episode Socials: @viallfiles @nickviall @justinkaphillips @the_mare_bare @izeweaver
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Discussion (0)
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All right, let's get to our first caller,
but not before you go on and give us a follow.
How's it going?
Hi, Nick.
I'm Mary.
I'm 25 and I have a crush on my coworker,
but I work in HR.
Oh, fun.
Well, what's your advice?
Well, so my,
My dilemma is, I know workplace relationships are pretty taboo in a corporate environment, and
HR is who puts all the policies in place.
So my question is, is this even worth pursuing?
And if so, how do I go about it?
I can give some background.
Yeah, give me some background.
Yeah.
So there's a guy I met at work a few months ago who I used to sit by, and our conversations have
always been really easy and fun and even flirty at times. Plus, he's like exactly the kind of guy
I'm looking for. Based off of what? So I've been single for a few years and I've gotten really
granular about what I'm looking for in my future boyfriend or husband. And he checks a lot of those
boxes and he's smart, he's respectful, he has good goals. We get along really well and he's just
really cute. Just to more accurately put that, he sounds like he checks some boxes. Well, we're still
getting to know each other. For sure. He might check all the boxes, but we don't, yeah, he's cute.
He has some nice things. I'm guessing you have more than four boxes is all I'm just putting out. Because I just
it's always important the things that we say to ourselves and out loud, the narratives we have
in our head become our reality. So be open to help you, I want to hear more of this backstory,
but in general, just as a, if we only had 30 seconds and you saw me in the elevator and I'm like,
Nick, I have a quick question for you. This is the advice I would give you, is just be more open
rather than right now you're giving the, I've taken my time, I spent the past few years,
being more discerning, learning about my likes and dislikes, and then I met this guy, he showed up
at my work, and wouldn't you know it, he's perfect? We don't know if he's perfect. We know that he has
some nice potential. And so I think just remember that as you explore the upside and the downside
of pursuing this guy. Absolutely. And just like with any kind of relationship, we're still just getting
to know each other. So it's just been surface level so far, but from what I've seen, he just is a
good guy. He's the kind of guy that I want to get to know a little bit better.
For sure. So yeah, my department recently moved to a different floor in my building. So I don't
see him as much anymore. So now whenever I see him, it's like when one of us is visiting each other's
desks. Do we visit each other's desks a lot? I probably see him at least once a day. And that's like
one of us having to go out of our way because we work in different.
parts of the building. So we've kind of developed a like a work friendship. And his relationship
status is single? Yes. I know for sure he's single. I'd never go after someone who's taken.
How old is he? He's 26. I'm 25. Okay. Yeah. And so this has been going on for a couple of months.
And I finally worked up the nerve and asked him to lunch last week. And it was really good. It was like
easy conversation. Like a work lunch?
It was, yeah, it was at work. Yeah, we have like a cafeteria.
I mean, at this, at this point, though, I mean, you know, works generally kind of boring.
I don't know what you do for a living, but like, I am sure people notice.
I've been careful about it and made sure that if any of our conversations were overheard or if we
never together. I'm not in any way questioning your professionalism. Obviously, you're,
you're hyper aware of it, which is part of why you're calling. I'm just simply pointing out, what's the average age of the people you're working?
with? Is it a spectrum? Yeah, it's a good mix. I would say it's average age is maybe like 40s.
Okay. Well, all those four-year-olds, they're noticing the young hotties flirting is all I'm saying. I'm just, you know, it's
probably fun. It's exciting for them. When I worked in an office space where I was on the younger side of
things, they talk about you. And all I'm saying is, I just certainly don't know the HR policies around this.
you know that better than me.
Sounds like there's a window here for you to pursue him,
but you're more worried about optics.
And I'm just telling you, they're already noticing.
You know, they're noticing two attractive people visit each other at work,
especially after one person moved to floor.
They're noticing a lunch.
And while they might wonder if you're just friends,
they are aware on some level that there are two single people of the office.
opposite sex who are attracted to the opposite sex, having lunch.
Is that not so innocent, just two coworkers having lunch?
I mean, the more innocent it is, the more fun it is to talk about.
I'm just talking about the 40-year-olds, many of which are maybe married with kids or whatever
in their life, are entertained by the single people, one of which is in HR.
You know, I'm sure everyone heard about the Coldplay story.
Yeah, exactly. That's what I'm worried about. He was married. It's just like he was married. I'm just saying,
don't dilute, like, they notice. And you don't need to do something about it. I don't think you
start acting weird. But like, let's not pretend that you're being so covert that no one notices
you guys hanging out and talking. Well, my company's policy clearly states it doesn't prohibit
relationships in the workplace unless there's a reporting relationship. And he's in an entirely
different department. The way my company is structured is that there's a different HR manager for
each department. And I don't work with his department. So I'd never have any kind of influence on
like his performance reviews, promotions, salary, nothing like that. How, what do you guys talk about
when, when you guys? We, we talk about, we've talked a lot about travel.
about like hobbies and our lives in general.
We talk a lot about work, but it's,
it's kind of gone beyond that.
Like at lunch,
we were just kind of talking about like our goals and stuff.
And like it just felt like more than coworkers.
Has you ever brought up women?
No.
That's good. Good.
Yeah.
And I know he's single because like we've talked about traveling for work.
And he kind of just like made a comment about, oh, like now is the time.
for me to travel since I'm single, no kids, that kind of thing.
How was lunch?
It was good.
And so I kind of want to take it outside of work.
I just want to see if there's something there, but that's where I'm struggling because
is that crossing a line?
Well, I mean, you tell me, is it crossing a line?
I don't know since the policy is not like stating that it would be.
but I just have never hung out with co-workers outside of work.
It's not something I would normally do.
Is that like the HR person you?
Because like despite your interest in romantically in this guy,
like coworkers hang out all the time outside work.
I think that is I just like to keep my work in personal life separate.
So this is all new to me.
And I don't know how to go about it.
Should I even be the one pursuing this?
Like, do I make the move?
Because I talked to my brother about it just to get a guy's perspective.
And he said, you kind of have to be the one pursuing him because as a guy, he's probably
not going to want to risk his job if he's worrying about coming too strong with the HR girl.
Your brother makes a valid point.
Yeah, I mean, yeah, especially in a workplace.
Yeah, I think a lot of young men in general are unsure.
unclear of when it is appropriate to make a move, regardless of the workplace and regardless
for this person who's in HR. I don't think that should be an excuse for men around the world.
I mean, like, you know, listen, just be a respectful guy, step up and make a move. It would be
my response to them. But just to give them a little grace and empathy, yeah, I think it's a little
trickier out there from them to know, especially young guys who are, you know, are an experience.
He's only 26. So, you know, it's all he knows is to be very, very difficult.
very aware of his surroundings and the surroundings of the women he's pursuing and to be respectful of
their boundaries. Like, that's, you're an HR and that's work. So, yeah, I think your brother's right
that, like, chances are. Yeah, there's a good chance he could be interested in and not do it out of
fear of the right or wrong thing to do. And, you know, there's a level of like, well, she's an HR.
She knows whether this is okay or not. So she'll ask me, you know. I know, but as a girl,
I've never been the one to chase after a guy or make the first move.
And it's just not the dynamic that I normally want.
And I definitely don't want to scare him off.
That's what I'm scared of too.
Because he's respectful and he's a little shy and he hasn't made any major moves.
But he's always...
So don't be so...
Don't be so...
I don't think you should walk up to him with a bouquet of flowers and say, well, you go on a date with me.
you could extend the lunch invitation from work to like,
what are you doing tonight?
There's this place I wanted to try, you know.
I'm so scared.
I have never done that before.
Good practice.
Listen, the days in which I never do this, I only do that,
especially when it comes to gender roles and things like that,
are outdated and antiquated.
I am guessing on some level you are a progressive, empowered, independent woman.
as you should be. Let's not cherry pick the handful of things that you're like, well, I am in all
those things, but this is the thing that I will never do. And this is a man's job. And he's,
you know, it's like, you can still, whenever, whenever you find your relationship, you can
define those roles and you can be when you want more demure and take a step back and you can
have your man lead. But I don't think when it comes to meeting your person, I think we should
be open to any possibilities. That's all I'm saying. And I think if you, being in the role that you are,
giving this situation and the dynamic of it, if you take it outside of work and you make the first move,
I don't think that makes him incapable of leading in the relationship if that's what you prefer.
There are a lot of situations I can think of myself, especially when it comes to dating, where I took a step back.
you know, I was nervous about making the first move or whatever it was. But I'm, you know,
I have a strong personality. In a lot of ways I lead in my marriage. There's a lot of ways in which
I default to my wife. I don't know. I think in 2026, the healthiest relationships have a balance
in terms of when people lead and things like that. And you will find that balance. And I think
it's just a little unnecessary for you to draw a very hard line because you've never done something.
And if anything, when you say out loud, well, I've never done something like that before,
it might be a signal for you to try it. You know, it might be a good practice. So if the only thing
that's stopping you is your lack of experience of asking them out outside at work, then I think
you should give it a shot. And again, I think you can do it in a way that's not too much pressure,
doesn't necessarily make it weird. You could even be like, I didn't ask him on a date. I had.
I asked him out to lunch. I have a friend at work. And I was like, there's this cool place I wanted to
try and pick a spot that's not overly romantic or dady. I don't could be literally anything. I don't know.
So how do I open that door? How do I like casually slip that into a conversation?
Where next time someone visits each other, maybe you wait for him to visit you. And you could be like,
I'm just kind of, I'm feeling a little like spontaneous. I really like, I don't know,
I want to get out. I want to feel the energy. There's this place.
want to go grab a drink. I don't know, maybe you don't drink. Whatever, whatever, whatever it is.
What are you doing tonight? He might be, he might have plans. Assume he has plans. But that will,
if nothing else, be an invitation for him that you wanted to hang outside of work. And if he's
remotely interested, he will be like, oh, sorry, fuck, I can't tonight. But what do you, you know,
like, I'm definitely down another time. You will know whether he is into it or not.
Yeah. And he has given signs, like, that he is interested. Like, his schedule's always busy,
but he never cuts our conversation short.
And if he's busy, he suggests the time when he's free to catch up.
And when I asked him to lunch, he immediately was like, yes, I'm free at this time tomorrow.
So he's definitely interested.
And I can just tell there's something.
So ask him.
It sounds like he's waiting for you.
Oh, my God.
I'm so scared.
Of what?
Of rejection.
Well, you know, it's good for you.
I mean, in general, failure.
I mean, I know not ideal in relationships, but it won't kill you.
And, yeah.
I think there's also just another layer to it because I would still have to see him.
No, you wouldn't.
If there are people, correct me if I'm wrong, on his floor, you never see or interact with.
You guys are going out of your way to see each other.
And it's not that hard because it's only a floor away.
Yeah.
But it would be just as easy to never see him.
or talk to them. Exactly. Like the stakes are pretty low. I just like get in my own head,
but there's just so many layers to this and lots to consider. Uh, probably no, no,
there's a couple layers. So try to get out of your head. Try not to add unnecessary pressure. There's one
layer, really. I'm in HR and we work together. And that makes things a little different than
any other guy I might be interested in dating. And I just need to make sure that I'm being professional,
which you are, so that if things don't work out, I'm not in any way affecting my or his
career or standing or brand at our place of work. Other than that, he's just a guy,
and this is how he met and I'm interested in, and it may or may not work out, but don't make it
more complicated than it needs to be. Yeah, I just need to go for it and not get in my own way.
Well, let us know. Yeah, I absolutely will. When are you going to do it?
I don't know, maybe tomorrow.
Great.
Love that.
Yeah, I will keep you guys posted.
So thank you so much, Nick.
Thank you guys for having me on.
Thanks for calling and good luck.
I think it'll go the way you hope.
And if not, you will be okay.
It'll be fine.
It won't be the worst day of your life.
It won't be the most embarrassing moment of your life.
It will suck for a brief period of time.
I hope it goes well, though.
I think it will.
I think it will.
Okay.
All right.
Wish me luck.
All right.
Take care.
All right.
Bye.
Bye.
Bye.
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How's it going? It's going really well. How are you? Good. What's your name?
My name is Sarah. I'm 29. How can I help Sarah? Well, I have been dating a guy for about 10 weeks now.
And we get along really well. Our values really, really align. We enjoy the same kind of
of things our timelines match up where like I am at a point where I'm ready to find a person I would love to have children and get married and he seemed to align with all of that I just I'm wondering like after eight weeks should I be more excited about him and I'm worried that if I'm not like excited about it like does that mean it's not right what do you mean by excited like when he comes over
I'm kind of relieved when he leaves.
When I know he's going to call me at night,
I kind of get anxious about it.
Has that always been the case?
Or has that a feeling that has increased over time until recently?
I think I was a little more, like, excited when it, like, the first date,
maybe the first two dates because, like, it was brand new.
And as I, like, got to know him, I felt like,
I should be feeling a little more comfortable with him than I am, and it just feels a little awkward.
And we started hanging out very regularly, almost like every weekend we would hang out a night or two.
And then Valentine's Day, like, was coming up, and I got him some things for Valentine's Day.
I knew he would get me something.
And I got him a card because I know they're super important to him.
It's something that he really likes and values someone writing down their feelings.
And I couldn't write in it.
because I can't I can't lie and like I don't miss him when he's gone and I don't know is this like
am I just experiencing something very healthy and I'm just not like excited and it's like I'm
confusing it for being boring maybe I don't know what do you mean what do you think how does this
compare your past relationships well that's the thing is I've been really trying to look at my
past relationships and I don't think I really don't think I chase like toxic
relationships. I don't think. I mean, I've been in toxic relationships, but I think I'm pretty easy to
recognize it and get out of it. And in whether it's been a healthy relationship or a toxic one,
I'm always usually like excited, kind of giddy. But thinking about the ones that you kind of
identify as healthy, but you were also excited. How is that different than with this guy? Because I was
excited to meet their families. I was excited to like see them and even if it was just like hang out
and watch a movie like I was pumped up about it and how like looking forward to it. Okay. When you
think back trying to as much as you can compare apples to apples here in terms of like timelines,
which I know is difficult to do. In these quote unquote healthier situations in which you felt
excited. Do you remember where you stood in terms of the certainty that this person really liked you
compared to how much you felt for them? I feel like in those situations, it was very equal.
Okay. Like, they liked me as much as I liked them. And in this, I, like, I know he liked me more.
Yeah, I mean, that part's clear. There is that. I think, whatever, I don't know what is where it comes
from, I think when we feel like someone's really excited about us, but we're still exploring,
you know, our feelings, even if it's nothing else. They don't give us the ick. They're not toxic,
whatever it is, but we're just like, at best, we're just not there yet, but we feel that they are.
That's a lot of pressure, you know. Yeah. And I, if nothing else, and I don't know, I'm not saying this is what's
causing your anxiousness, but it would make sense. The reason why you're not excited and feeling a little
anxious when he calls and when he shows up is because you feel this pressure to do something.
You feel like he has an expectation, the card to write something. You don't know how to meet
that expectation right now. So you feel anxious. And right now you're spending a lot more time
trying to meet his expectations in a way rather than evaluate how you feel. And obviously,
you've been evaluating it. You're here talking to me. You haven't been able to evaluate
it by just kind of being with him. And listen, it easier said than done, you know, I'm sure you've
heard mine of my wife's story, Natalie's story about how we met and, you know, first nine, 10
months, so Nick didn't want to date me and things like that. And certainly, there were a handful of
moments where Natalie was like, yo, what's up? In between those moments, I don't know how she did it
or what her mindset was. Maybe if you get a chance to ask her, you can tell her, she can tell you
someday. But she did a great job of not making me feel like there was pressure. It wasn't like,
it wasn't like after a couple months. She's like, hey, I'd really like to date. And I was like,
I don't know. I'm just not sure. You know. And then she was like, okay. But then like, you know,
but like whether she said or not, it always felt like she didn't always feel frustrated with me.
She wasn't making comments. She wasn't doing X, Y, or Z. She made me feel like she, I guess,
accepted my answer or accepted my boundary. And then a certain amount of time passed where then she was
like re-evaluated how she felt brought a new expectation or standard of the table and yada yada yada.
If nothing else, his expectation or how you are feeling or how you are internalizing his
expectations, maybe he's not doing all that much. But if nothing else, this anxiousness that you
feel is a result of this pressure that you have placed or he has placed on where this relationship
is going i would say another question like to bounce off of all of this is that i don't think he's like
a two but i also don't think he's like obviously a 10 and like i he's a five so he's a five
and that's fine and i don't have like i don't think the looks thing is like the problem for me
it's more of like when he kisses me like i i'm just not into it and i don't know if like that's something
that i should like work on with him and like try to make things better but then at the end of the day i
feel like i'm like nitpicking and like trying to hold this person into well i mean is he is the
chemistry when you kiss off by chemistry i mean like maybe the tongues aren't tonging you know like
maybe you guys aren't dancing the way you guys need to dance
And if that's the case, sure, give him a note.
But, like, if you're like, oh, no, he's actually a great fucking kisser, shockingly.
So I'm just not into it.
Yeah, I guess I don't know because he's not a good kisser.
So I'm just, like, very turned off by those things.
And it's just like every little thing feels awkward.
Why are you still hanging out with them?
Well, that's the thing is, you know, we're always told, like, hey, there's no perfect person out there.
And you are going to have to have, like, a give and take and a compromise when it comes to
somebody and that's why I'm like I need to know I want to know from you is attraction and feeling
like that chemistry that like pull to like lean in versus lean out something to compromise on
I think you need something all the other things what are the other things um that the fact that we value
the same things we live the same sort of lifestyle we care about being healthy and active and family
people and you know we are around the same age we're both looking for marriage and kids and
he was so so there for me on the toughest day of my entire life and i think that like i know he
cares i know he has interest i know that he puts forth effort and like takes time out of his
day to do certain things and like i value all of those things so much i just
just feel myself leaning out versus in.
And like I like him more when he's not around versus like I try to like shut my brain off and like just.
Are you guys boyfriend and girlfriend?
I mean, he asked me like two weeks ago to be his girlfriend and I said yes.
But I mean, it's like I said, it's a very new kind of thing.
I don't see this as like we're not in a serious relationship at this point.
It's the beginning.
I'm just curious how you would respond to finding out that he met someone else and started dating them and is interested in them.
I think the only reason I would feel any sort of way about it was because he asked me to be his girlfriend and there's like those things.
And because he and I have been exclusive.
But other than that, I don't.
I mean, I think maybe there's a better person out there for him than me.
Okay.
That sounds kind of like you have your.
Like,
someone who can, like, love him more and, like, be, like,
if someone's telling me, like, I want to take pictures with you and post you,
and I want you to meet my family and stuff like that,
I would hope that your person you're seeing is excited about those things.
And, like, I think he deserves that.
I mean, if Natalie would have told me that, I mean, hell,
even after we were boyfriend and girlfriend a month in,
I would have been, like, a little, like, anxious about that.
I'm like, okay, calm down.
And that, honestly, it was probably more of a me thing.
You know, I was, as we've discussed, he is excited about you in this relationship.
And so these things that he is asking are normal and okay.
You're not ready.
That's fine, you know, and that's why it feels a certain way.
It overall sounds like, listen, you have the answer, which is like you don't, you're just not feeling it.
A lot what you're describing is you have a lot of compatibility.
You have a lot in common.
That is really important.
but chemistry is really important too.
You know, I think we all vastly overweight chemistry.
Yeah.
And ignore compatibility.
There are some relationships out there are solely based off of how two people felt when they first met,
or the first couple weeks of dating.
And their entire relationship is solely based off of that and the fantasy that they built in their head of what the relationship should be.
And then that, and then, you know, it's not.
But listen, you've challenged yourself to at least explore this for eight weeks.
That's not nothing.
You'll never know for certain.
There's always a world where I guess you could miss him.
I do know that when Natalie and I were dating and I was having a hard time letting her in,
when we would try to have some distance, it would be very difficult for me.
I would definitely miss her.
And that was something that was pretty obvious to me.
So listen, if you let him go and that will be really sad,
for him. But if ultimately, if you're not feeling regret and if you're feeling relief and a few
weeks go by and you don't miss them and you're not feeling any type of jealousy or wondering
what he's doing, and then you'll have your answer. Yeah. Just one more little question is like,
you know, I do think most people do, like you said, value that chemistry, like maybe way more than
somebody should, but do you think that that's like a necessity for a relationship?
I think it's a personal preference. I'm sure you've heard the anecdotes about how the success
rate of arranged marriages and the cultures that still practice those marriages, you know,
there's a reason why. If this was an arranged marriage, if you were part of a culture that
did this, you would be one of the lucky ones, so to speak. You'd been like, this is a really great
guy. He treats me well. We have a lot in common. Like, he found a friend. And then
over time, you would probably grow that emotional connection and you would grow to care about him
and you guys would form a bond and you would probably work on the sex and the kissing and things like
that. And, you know, there's a world where like you could really grow to love him. I don't know,
but you're not in that culture and you don't want to have an arranged marriage and you want to pick
your partner and you want to find someone where you at least feel a little chemistry and some,
you know, a little bit of excitement. But part of that maturing is discerning the difference between
how much of this is pulled by a chemistry and you convincing yourself you have a lot in common
or being pleasantly surprised. You know, for me, I got it, you know, like, it's in a weird way.
My reluctance around our age difference, I think, helped me, you know, and I think, like many people,
was often choosing partners mostly based off of chemistry, only to find out we didn't have a lot in
common. But chemistry, you know, if you, you know, I always joke when we were watching love is blind.
and love is not blind for me.
I could not do that.
That's kind of what I was thinking last night as I was watching that.
And I got lucky enough that I met someone who I did have a ton of chemistry with,
but I obviously there was a reason why I was unwilling to kind of pursue that.
And then while we stayed each other's lives but kept a little bit of distance,
I realized, despite my insecurities about things,
how much we enjoyed each other's company, how easy it was to hang out with her,
you know, her timeline, her values, all the things that you described. And it was like, wow, I was able to
discover that over time. I didn't do the thing that I had done in the past where I didn't really,
I didn't care about compatibility as much as I should or, yeah, it just kind of happened. So listen,
it'll work itself out. It doesn't sound like if, listen, if you break his heart and you end things
and you do it respectfully and with gratitude, if you change your mind, chances are, he will be glad that you did.
And you will probably, you know, it probably won't take you long to realize whether you felt like you made a little bit of mistake or not.
Chances are you probably didn't.
You've given it eight weeks.
You hung up with him multiple times, but something isn't feeling right.
And you found a nice friend.
You respect them, but like he's, you know, not your guy.
Oh, thank you so much.
I really think that I, I don't think I value chemistry too much.
I just have realized that it is something I do need is like a pull towards each other.
And I think that just goes along with like the things I want as in like compatibility and timeline and all of those things too.
So this is really helpful.
All right.
I really appreciate your time.
All right.
Thanks for the call.
Thank you so much.
All right.
Take care.
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How's it going?
Good. How are you?
Good. What's your name?
My name is Bree. I'm 23 and I need honest third party advice on how to date better in my 20s.
What do you think you're doing wrong?
Well, I'm on the apps and I also like do go out here and there and like try to meet people in
person, but I just don't know what the issue is like for me specifically with the apps.
I feel like when I go in person, maybe people don't recognize that I'm like of age because
it look like younger and I don't drink.
So maybe that hasn't to do with it.
Okay.
Well, just like, give me an example of kind of an experience.
I mean, it sounds like you're calling in because you've had a couple of experiences that
didn't go your way.
And now you're feeling a certain way about dating in general.
I've been on, I've been on hinge since August.
But basically on the apps, where I've experienced is people, they match with me.
They don't say anything.
They either don't match back with me.
They match with me.
They say, like, one, like, sentence.
And then I don't hear from them again.
they match with me, I get their number, then I talk to them for like a day, then I never hear from
them.
And then the other day, I literally got an argument with somebody from the app.
You argued with someone on the apps?
They, okay, so they basically, I asked them what their Instagram was and where they lived,
just to make sure, like, that they lived in my area because I didn't recognize the location.
And they said, I was asking all these pressing questions.
And then they gave me a whole spiel on how I need to communicate better.
So, and that my communication sucks.
they're helping me for my future husband.
You were asking them questions and they said your communication sucks?
I asked them what their Instagram was and like where they live.
And I stated like, I don't like long distance.
So I'm just curious like, do you live here because I don't recognize the location in your profile?
And then the guy literally said to me, you're asking me all these pressing questions.
We just met.
And I'm like, I don't think my questions are like that ridiculous.
Okay.
They're not.
So I mean, are you like relatively new to dating?
you mentioned you got on the apps not too long ago. What is your dating experience been like up into
this point? So I've had two previous relationships. One was the seven-month relationship when I was in my
freshman year of college. And then one was a year and seven months. That one, I've been single since
that one for like a year now. Okay. In between that, have you just been kind of enjoying the single
life and hanging out with your friends? Have you done not much dating in between? I've gone on some
date. One was the really nice guy, just the distance and like his work schedule was just
it didn't work out. And then one, the date went well and it just didn't work out. And then I went out
with a different guy. He thought I was moving too fast and I thought he was moving too slow. So we
were just on totally different wavelengths. Okay. What else? I mean, I guess when you wrote in,
is it mostly your frustration on the apps or just dating in general? I guess dating in general because
I feel like I go out when I do go out and I haven't been out in a bit because sometimes
my friends don't always want to go out. They want to have a night in, which I absolutely understand.
And so when I go on the, when I go out, like, I sit here and I'm out and I'm trying to like
maybe see like if a boy will approach me. And I've gotten approached by a couple guys and they're like,
oh, I don't live here. And I'm like, and then one of the guys I went out with, I met out,
but that was like the only guy I met out. And I've done the happy hour, gone to the bars and things.
and just because I've gotten nowhere.
Okay.
And how long do you feel like this has been going on for you?
I went on the app in August.
So I've had really not much luck there.
And then I started to go out more because I used to not go like out really at all.
And my mom's always like, you need to go out.
Like the other day, she's like, if you don't go out, you're going to, she's like,
do you want to be single for the rest of your life?
And I was like, no, well, no.
Is your mom like giving you a hard time about your dating life?
No, she just wants me to be happy and find my person, which I can
really understand but she's like you need to go out that's another way you can meet people like
yeah that that's really that's really it and I'm just I guess I wonder like is something wrong in my
dating profile is like what's on your dating profile I feel like I'm very like open and like
very clear with what I want and like just very true to myself and so when I'm on the app what is your
dating profile say well I can go through it but basically um on the app I have in my profile I have like
my photos, like, of myself.
And then...
Mostly just you?
I have my thing, like, my love language on there.
And, like, my friend's advice and my sister's advice was get rid of, like, all the
multiple repeated selfies that basically are the same thing, like, change your photos
a little bit.
So I did that.
Do you have any, like, activity photos?
I don't, but I have a photo of me and one of my friends.
So I have that up there.
And I kind of just, like, put that, like, and like, I get, like, positive feedback on, like,
certain things I have like dating me is like I said like being in a romantic relationship where
you're like love 24-7 and like it's full of making memories and that a last lifetime it's like being
beloved and at the same time being like supported and like being a relationship full of happiness
like that one always gets like the most hits and then I see I have one that's like my simple
pleasures are spending quality time in my person getting sons spending time my friends of
family my two dogs watching reality TV going on walks and then like the way to win me over
like respect, honesty, kindness, being on the same page, sharing common interests.
So that's huge for me, wanting kids, being, and by being a provider and a protector.
So I have that on there.
And then I have, like, photos of myself and then the prompt of, like, my love languages
are this and this, although I really kind of like all of them.
That's kind of on there as well.
So I think part of my issue is I have a very specific type, and I have, like, very high standards,
I feel like.
So when I go on and like I see like I have like certain matches, I'm always just like no, no, no.
And then like if I do have interest in somebody like I said, my problem is that like I get their number.
I talk to them once.
I talk to them on the apps and have like one conversation and they don't hear from them again.
I like them.
They don't like me back.
I match with them.
They don't even message me.
They just match with me.
Don't even say anything.
Yeah.
I'm glad you're getting this all out.
You know, you're defending.
It's good.
What do you think I'm going to say?
Take a break from the apps.
If you want to.
I think more specifically, I think you just need to maybe take a breath.
Okay.
You know, I don't think you're doing anything wrong.
I mean, like, you know, if I, like, shadowed you for a week, I'm sure he'll give you a note or two.
The problem isn't you.
I mean, there's a lot of problems when it comes to dating in 2026, hookup culture, the apps, things like that.
I think right now, you know, the way you talk about the apps is it's like everyone's on the
apps, which they are.
It's the only way to meet people, which it isn't.
It's certainly where most people are meeting each other these days.
It has a lot of obstacles.
So I think for anyone who goes on the apps nowadays, especially if you're trying it for
the first time and you don't really have, you're not like a seasoned vet on the app where you've
kind of, you've realized what it is and what it isn't, and you kind of have an objective
expectation of it is to have the lowest of expectations of the app. And at this point, I do think
the apps, they're not designed to help people find love. They are designed to get people to stay
on the apps. That's all apps are, you know, they're there to make money and they only make money
when people are using them. And if everyone in the world found love tomorrow, there'd be no one to
go on the app. So you're like, you know, you're only 23. I'm sure it doesn't necessarily feel like,
I've said this all the time.
Today is the oldest you've ever been.
And when you think about your age, especially when you get into our 20s, it starts feeling
like you're like, oh my God, I can't believe I'm 23.
And you've never been this old.
And I'm sure from your perspective, you don't feel as young as I look at you and say, oh,
she's only 23.
She's got this whole life ahead of her.
And so I think, you know, it's great.
You know, I think your mom's right.
Get out there, meet people.
But I think you just need to take a breath when it comes to finding love.
I think there's a difference of being intentional to like tell your.
yourself that you are focused on meeting your person and you're open to meeting your person
without like applying so much pressure on yourself and making it an obsession where every,
you know, every time you go out, it is to find a guy as opposed to I'm going to go out and
hang out with my girls. I'm going to have a good time. Maybe I'll meet a guy. I'm going to open to
meeting a guy. I'm certainly not closed off to meeting a guy. And maybe I'll be surprised. You know,
you kind of always have to go out with this kind of like curiosity and open to being
surprised rather than going, whether it's on the apps, whether it's going out to the bars,
make it your whole mission so that if it doesn't happen, you leave disappointed. You should have
zero expectations on the apps, right? Like it's just a bunch of strangers. You have no idea
who these people are. Hell, you don't even know if they're real. You know, you don't know how updated
their pictures are. It's really important for you to trust your gut. So when you are saying,
hey, can I see your Instagram?
And he comes back with a, that's too personal.
If you're like, well, no, it's not.
Immediately at that point, save all the energy that you wasted with this guy and just know
that, yep, this stranger, this person I don't even know is real.
For all I know, it's a bot is not my guy.
I'm going to move on.
You just immediately unmatch.
You know, you knew nothing about this person other than a couple pictures.
You asked a very basic question.
He took it.
exception to that and let you know that you guys weren't on the same page. Before you even met this
guy, he was like, we're not on the same page. I mean, immediately just unmatch, you know, not,
you know, it's not to be rude. You don't have to like, you don't have to be mean about it. You could just,
oh, okay, well, if he thinks that's personal, I think that's normal. I mean, I've known,
I've communicated to the stranger for five seconds and already, we're not on the same page,
you know? So like, don't waste, don't get in a fight with people. You're fighting with strangers.
For all you know, you're fighting with a robot.
Do the little things to help yourself out, right?
Because, again, dating is frustrating.
It's exhausting.
This paradigm, I don't know if a paradigm, you know, whatever.
I mean, sometimes they just throw out words.
I don't even know the meaning.
And the most frustrating thing about love and dating, especially in 2026, is that we still
want to find something special.
We still want to find something unique.
We still want to watch the notebook and feel like, yep, the love I found with my,
person is as euphoric is these crazy characters in this movie. But we also like don't want it to be hard.
You know, we don't want to have to write 365 love letters in one year and, and wait 20 years to
find love like they did in the notebook or whatever. Like we want it to just happen. We want,
you want to go on the apps for a couple months, swipe a few times, go on a couple dates, and you
want to meet your guy and have it be like amazing, which I get. I mean, we all do, you know,
but that's just kind of not realistic. So dating is about going on 10 dates just to like one person.
I mean, that's dating. And that one person doesn't mean it's going to be your guy. It just means
it might be the person you, like, are interested in it. And maybe they're not interested in you.
And it might take 20 dates or 20 matches at least to find someone who's like there's a mutual
compatibility and then you date that person for a period of time, only to realize, while they were good,
they weren't great. You know? And that is, unfortunately,
reality of dating. And that does sound exhausting. And it is exhausting. But the thing that you can do
to help yourself is to not waste your energy on things that you know are a waste of time.
Like the guy who's like, that's a personal question. You're like, that's literally, you think
that's personal? We're not, you know what I'm saying? Like to not get frustrated, you know,
like going on the dating apps, just know, you're going to see a lot of bad options. And instead
of getting discouraged by all the people you don't like. You yourself said, I'm picky. I'm
picky. I'm particular. I have high standards. That's awesome. Well, you can't have high standards
and like everybody. High standards requires patience and high standards in anything, whether it's,
you know, if you had high standards at your job, you know, you would take a little bit more
extra time to make sure it's done right where other people might be like, yeah, I'm done. I don't
And you might be a little bit more patient to check your work, to make sure it's right, to review it.
And yeah, high standards requires patience.
And a lot of people in dating like to say, I have high standards.
I'm picky.
And that's true, but they also don't have the patience.
They're like, I've been on the app for four months.
What the fuck?
You know, I think overall, you're doing everything fine.
You're over-analyzing your dating app.
You're like, well, this one got the most engagement.
I mean, like, listen, it's hookup culture to the max right now, not to discourage you,
but I would venture that most of the guys on the app, you know, they might read that and go,
oh, that's sweet.
And maybe they want to get married someday.
But most of them are probably looking for a hot date and maybe a fun hookup.
The energy that you are using to be like, to find validation and people liking,
your profile isn't doing you any good, you know?
Again, use the apps, but just have a very low expectation.
Most people are on it playing hot or not.
I would maybe check in.
I mean, I would limit your time on it and just, you know, again, you know, have fun with it.
Just goof around.
It is a silly thing.
It's become comical apps, right?
But you can still meet people, right?
Like, I met my wife on Instagram.
So, like, it can still be possible.
But, like, you shouldn't be like Instagram or the dating apps are,
my key to like finding, you know, it's, it, there are doors and windows to rooms you want to fill.
So leave them a little cracked open, you know, don't close yourself off, you know, be open to meeting
people. I really think we're going to, you know, like, I saw this graph like, you know, how people
met their partner, you know, from like 1950 to now, right? And it was just kind of talking about how
the internet has taken over. And at this time, it was like, you know, zero people met on the line
because online didn't exist, right? And then most people,
met people through friends and family, church, school, college, whatever. And obviously, now it's like,
now 60% of people are marrying their person online. And I think over time, there'll be a bit of a
renaissance for a shift. I think your mom is right. I think the more you just can get out there and
engage with people in the real world and slow down and just try to meet people and have fun
with people, not with the expectation of finding a husband, but just to meet friends. And when you
find a spark, lean into that, ask questions. But like, just know.
that even in the real world, like, as a picky particular person, you are not supposed to like
everyone and they are not supposed to like you. Don't get discouraged when you go out on a Friday
night and you don't meet a guy. You're probably not going to meet a guy. When I was the
bachelor or every bachelor or bachelor who's ever gone on that show, the show is, you know,
they're saying, we have found the 25 or 30 most eligible people in the world. And then every
lead who like goes out there, they're like they may be like to. And that's because, you know,
because we all are all picky and we're not just going to fall in love with anyone. It doesn't matter
if they're all attractive people. It doesn't matter if they're all like fairly like good catches,
you know, for a lot of us out there. The bachelor casking can go out and find like the 25 most
eligible people and that one lead is still like, I don't know, maybe two, you know. So think
about that when you go out to the bars. You know, you could walk into a bar and have a bunch of
guys and you're not supposed to like fall in love with any of them. If you do, great. And that's why when
it does happen, you have a hard time sleeping because you're so excited, you know, you're just like,
this is, oh my God, this is this person real, you know? And even then, you might find out to
be a total piece of shit. And then they may not like you. But like, I think you just have to
slow down and enjoy the journey a little bit. Have some fun. And stop being so hard on yourself.
And when things don't work out, whether it's online, certainly online, or out at the bars,
you don't have to overanalyze what am I doing wrong.
It's just part of the process.
You should just be like it's just dating and kind of take it easy and yourself.
Yeah, I think I need to focus on doing that more.
Like I said, when I go out, I do try to, you know, just have fun and whatever.
And I go out to be with my girls.
I don't go out to like, well, I go out with the intention of like wanting to meet someone, but like,
not with the end, like the end goal of it, obviously.
So, yeah.
So again, you're doing all things right.
The only thing you maybe need to change is your, I guess, analysis of the results of these evenings and just be patient.
Honestly, that's to sound corny, but just keep a positive demeanor, have good energy, be engaging with people.
and I'm saying this is someone who's more introverted
and I don't walk outside in the public rooms
like being like like you know focus on being the friendly as purpose
I mean I'm married you know it's like but if if we want to meet people
we have to we have to show up into rooms with like a welcoming energy
a friendly demeanor and that will attract people we don't want to talk to you know
so again there's that catch 22 but again you just you know try to just make connections
with people and I promise eventually to work out
out, but you just have to practice patients.
Yeah, because I feel like I'm very outgoing.
I can make friends with kind of like anyone.
And I don't have a problem like approaching people.
Obviously, like if I'm looking, if I'm out, like I want a guy to approach me.
Like I don't really want to approach them.
But like I can make friends with anyone.
Like if somebody approaches me, I can be friendly.
Like it's not a problem for me.
So I don't think that that's really my issue.
I just wonder like, do people think I'm not of age because like I do look younger and I don't
drink?
Like, do is that part of my issue?
Like, do people not just...
You're over-analyzing.
I mean, you look 23.
I mean, if you told me you were younger, I'd also believe that.
I mean, your age ambiguous is it relates to like being, yeah, I would have guessed somewhere
in your early 20s.
I don't know.
You know, and again, I wouldn't listen to people in their feedback of whatever they say they do.
Most people are just, if they meet someone in a dating situation that they don't want to
continue, think about what you would do.
You would probably, you're just trying to get out of it, right?
So you're trying to say the thing.
that you think would be the least offensive
that sounds legit.
And, you know, so like, I wouldn't listen to the feedback
from people you barely know.
And I wouldn't listen to the feedback
from anyone online because you don't know them at all.
Listen to your friends, listen to your mom,
but most importantly, listen to yourself.
And I think trust your gut,
you have good instincts, and just be patient.
And really just, it's having the patience
so that you don't constantly critique yourself
and second guess yourself.
and definitely stop over-analyzing and listening to the feedback of strange men.
I'll definitely take that advice for sure.
Was this helpful?
This was definitely very helpful.
I'm definitely just going to let things happen naturally.
That's really my goal at this point because I'm on the apps and I'm just kind of like
it hasn't happened yet.
And with what's been going on, I'm kind of like, I don't really have like, oh,
it's going to happen tomorrow kind of mindset anymore.
I just kind of sit there and I'm kind of like, I'll keep the apps because you just never know.
but at this point, I'm not going to fully rely on them because it's just not working.
You're only 23.
So enjoy this.
Have fun with your friends.
Like don't waste 23.
And this advice I would have given to my younger self, being pressed that you haven't found the one yet.
Okay.
Be intentional.
Be open.
Be positive.
It'll happen.
Okay.
All right.
Thank you so much.
All right.
Take care.
Have a great day.
I love your show.
I'm a huge fan.
listen to Ask Nick all the time. Well, thanks for listening. I already listened to Monday's episode. I loved it.
I appreciate you. And I tell all my friends about it and I tell them to listen. I love that.
I appreciate it. Making my car rides to work somewhat better. Well, thank you for listening.
And as you continue dating, if you have a meaningful update where you feel like, you know,
this was kind of a nice moment, let us give us an update. I definitely will. Thank you so much, Nick.
All right. Thanks so much. Have a great day. You too. Bye-bye.
