E1152 - My Best Friend or My Fiance? | Ask Nick

Summary

The Viall Files – E1152: My Best Friend or My Fiance? | Ask Nick

Host: Nick Viall
Date: July 6, 2026
Co-Hosts/Household: Natalie Joy, Sally, Sarah, Molly (Callers)

---

Episode Overview

This "Ask Nick" episode of The Viall Files centers on three callers’ nuanced relationship dilemmas—balancing loyalty between friends and partners, navigating post-hookup awkwardness with an old flame, and dealing with “that guy” in the family who causes everyone to tiptoe. Nick, joined at times by the Household, provides his signature direct, compassionate, and humorous advice. The episode explores themes of boundaries, conflict resolution, self-awareness, and the inevitable messiness of adult relationships.

---

Key Discussions and Insights

1. Molly—Should I Invite My Best Friend to My Micro Wedding?

[01:43–26:00]

Background:

• Molly (31) is planning a micro wedding (10–15 guests).
• Wants to not invite her high school best friend due to drama/history with fiancé’s friends.
• The friend holds a grudge from high school cliques and a complicated past involving her sister and one of the fiancé’s friends.
• Molly describes her friend as "abrasive" and worries about potential conflict at her very small wedding.
• The friend has also made odd, self-centered overtures about planning Molly’s bachelorette.

Advice and Discussion:

• Nick encourages Molly to have an honest but kind conversation with her friend before making a final decision—giving her friend a “chance” to promise adult behavior rather than an outright uninvite.
• Quote:
  • “Are you willing to uninvite her and be honest with her without at least giving her a chance? … I feel like if you want to keep this person in your life as a friend, she deserves an opportunity to at least hear that, you know, and … to say, ‘I can promise you I won’t make it about myself on your day.’” – Nick [08:35]
• Nick notes the value in facing discomfort for meaningful relationships, drawing parallels to his own willingness to confront conflict for the sake of authenticity and growth.
• Advises Molly: don’t let your aversion to confrontation ruin the friendship or wedding; your priority is your relationship and your joy.
• On wedding drama:
  • “I think people underestimate the value of a little drama and a good story at a wedding. … Your job on your wedding day is to not care about any of these people.” – Nick [12:03]
• Nick frames the situation as a chance for Molly to practice setting boundaries as an adult, not just in this friendship but for her life ahead.
• Action Plan: have the conversation, set the boundary, then decide.
• Concludes:
  • “As you move in this part of your life, you don’t have time for relationships that no longer serve you. … She needs to show up as your friend today.” – Nick [22:53]

---

2. Sarah—Is It Confident or Desperate to Double Text After Rejection?

[27:28–56:29]

Background:

• Sarah (31) hooked up with an acquaintance from the past (recently divorced), who then left her on read after she texted expressing her desire to sleep together again.
• Some continued surface-level texting, but he has not addressed or reciprocated her sexual overture.
• Sarah is a busy attorney, generally avoidant of “hookup culture,” and feeling frustrated about her dating life—wants a hookup but also struggles with finding a partner she’s genuinely interested in.

Advice and Discussion:

• Nick immediately tells Sarah: “It's definitely more desperate than confident." – Nick [27:43]
• He emphasizes that pursuing someone who is unresponsive signals misaligned intentions and possible neediness.
• Sarah unpacks her wish for “an easy summer hookup” but acknowledges she still has a longstanding crush and is prone to overthinking.
• Nick underscores gendered nuances—“If roles were reversed, it would come across differently…”—and urges her not to pursue or pressure.
• Notable Quotes:
  • “The easiest way to make a non-awkward situation not awkward is to not make it a thing. And you're trying to figure out how to make it a thing without making it a thing. And that makes it a thing.” – Nick [34:10]
  • “You’re a very busy, accomplished person with limited time. So, my advice is to do things in the dating space that help you get to your goal.” [48:11]
• Reframes Sarah’s desire: her search is less about sex, more about companionship and intimacy.
• Nick challenges her to examine whether her dating actions actually serve her end goal of a meaningful partnership.
• On dating effort:
  • “Busy people can still make time for what they want. … You need to put yourself out a little bit more…and you definitely will survive rejection.” [54:13]

---

3. Sally—My Best Friend’s Boyfriend’s Brother (Greg) Is a Problem. Who’s Actually to Blame?

[60:07–76:11]

Background:

• Sally (32) calls on behalf of her best friend, whose boyfriend’s brother, Greg, is a major source of friction.
• Greg introduced the couple, but now resents the relationship and exerts outsized influence within the family (e.g., the girlfriend is excluded from family events due to Greg’s discomfort).
• The boyfriend is passive; won’t stand up to Greg or assert his own boundaries.

Advice and Discussion:

• Nick swiftly reframes the issue:
  • “The brother's not the problem. The boyfriend's the problem.” – Nick [63:24]
  • “If she's being excluded by the family, the only one who's going to do something about it is the boyfriend. … There's no convo she needs to have with Greg. The only conversation she needs to have is with her boyfriend.” [67:00]
• Highlights the real red flag: the boyfriend’s unwillingness or inability to advocate for the relationship.
• Notes possible misaligned timelines and warns Sally’s friend may be projecting her own readiness onto a younger, less mature partner:
  • “There's a big difference between knowing you want to do [marriage] someday and being ready for it.” – Nick [66:41]
• Sally provides context that the family tiptoes around Greg, who’s always been temperamental. Nick calls out that every family has a “Greg”, and the best way to deal is not to engage with that drama.
• Action Steps:
  • Focus only on what the boyfriend does about the situation, not on changing Greg.
  • Assess whether the boyfriend is truly ready for commitment, or just saying what’s convenient.

---

Memorable Quotes & Moments

• “I think people underestimate the value of a little drama and a good story at a wedding... Your job on your wedding day is to not care about any of these people.” – Nick [12:03]
• “The brother's not the problem. The boyfriend's the problem.” – Nick [63:24]
• “You need to put yourself out there a little more. Busy people still make time for things that matter.” – Nick to Sarah [54:13]
• “Sometimes people say they’re not in a rush as an excuse to not do things that match their goals.” – Nick [50:01]
• Molly’s insight on friendship: “In good friendships, you should be able to tell them how you feel. This conversation is a good barometer for whether she cares about my feelings.” [22:28]**

---

Important Timestamps & Segments

| Time | Caller/Topic | Key Theme | |-------------|---------------------|--------------------------------------------| | [01:43] | Molly | Disinviting a best friend from wedding | | [09:26] | – | Molly’s struggle with conflict | | [15:07] | – | Micro wedding concerns/guest list | | [17:19] | – | Bachelorette planning drama | | [21:12] | – | Boundary-setting as adult skill | | [27:28] | Sarah | Is double-texting “confident or desperate”?| | [34:10] | – | Overthinking and mixed intentions | | [44:08] | – | Companionship vs. just sex | | [48:11] | – | Aligning time investment with dating goals | | [60:07] | Sally | Interference by boyfriend’s brother | | [63:24] | – | Problem is boyfriend, not brother | | [68:47] | – | Discussing the move-in timeline | | [72:31] | – | Family dynamics & Greg’s unchangeable nature|

---

Episode Takeaways

• Have the tough conversations: Even if you hate conflict, speak your truth to friends and partners. If they can’t handle it, they might not belong in your future.
• Who’s really the problem? When friends complain about “in-law” or family drama, look at how their partner is showing up (or not) for the relationship.
• Intentionality matters in modern dating: Actions should align with your true goals, not just your momentary desires or avoidance of discomfort.
• Some drama is inevitable: Whether in friendships, family, or romance—sometimes a little messiness or “bad behavior” is just part of the ride. Protect your joy and your peace, but don’t expect it all to be conflict-free.
• Boundaries are key: Lifelong friendships—or family ties—require evolving boundaries. Setting them is both a skill and an act of self-respect.

---

This episode is invaluable for anyone weighing friendship versus partnership, hesitant about confrontation, or wondering how to balance adult obligations with their own happiness. With Nick’s signature blend of candor and insight, listeners are reminded to protect themselves, communicate openly, and—when in doubt—put their real priorities first.

Transcript

[Host]

Insurance isn't one size fits all. That's why drivers have enjoyed Progressive's name your price tool for years now. With the name your price tool, you tell them what you want to pay and they'll show you options that fit your budget. So whether you're picking out your first policy or just looking for something that works better for you and your family, they make it easy to see your options. Visit progressive.com find a rate that works for you with the name your price tool. Progressive Casualty Insurance company and affiliates Price and coverage match limited by state law. Awkward time to ask this, but. Hey, did you download the trail map?

[Molly]

Yeah.

[Host]

No, I don't need to.

[Sally]

I don't understand.

[Host]

You're trusting your signal out here.

[Sarah]

I'm trusting T Mobile.

[Host]

They have the best network.

[Sarah]

And if we end up in bumtots nowhere, well, we've got T satellite for backup. Whoa.

[Host]

I don't trust my carrier that much. We'll just use your phone as a flashlight. With America's best network and T satellite, we're keeping you connected in places you never thought possible. And if you switch today, you get free phones for zero now and only 25 bucks a month per line for four lines. Find out more@t mobile.com or visit your local store.

[Announcer]

Best Mobile network Based on analysis by Ooglo speed test intelligence data 2H 2025 with 24 monthly bill credits and 4 eligible port ins on essentials for well qualified customers with autopay plus taxes, fees and 35 connection charge per line. Credits and imbalance too. If you pay off earlier, cancel contact US Finance Agreement example 299.99 Moto Edge 5G required T Satellite available with compatible device in most outdoor areas in the US where you can see the sky included with experience beyond or $10 a month. However, news monthly cancel anytime Visit T mobile. Com.

[Molly]

You're crazy.

[Host]

How's it going?

[Molly]

It's going well. My name is Molly and I am 31 and I am calling today because I have to tell my best friend from high school that she is not invited to my wedding.

[Host]

Why do you have to tell her that? And why is she not invited?

[Molly]

Both great questions. So I feel like I owe her the courtesy of telling her that she will not be invited. She knows that this event is happening. She has tried to insert herself in my bachelorette party that I did not ask for. So I feel like it would be difficult to maybe not tell her because it's an invitation she will be expecting and she is not invited because unfortunately she really, really Dislikes. My partner's friends.

[Announcer]

Okay.

[Host]

Like. And what. What do you mean by really, really dislikes?

[Molly]

So this is my best friend from high school, and my. I also met my partner in high school, and he is with many of the people that he was friends with in high school. So we all know each other. And unfortunately, there are a variety of different reasons why she. She doesn't like them. I think on one hand, although this was a long time ago, we weren't cool in high school, and my partner and his friends were, and she holds some resentment about that. She thinks people still see her the way she was in high school, even though I. I beg to differ. I don't think anyone still thinks about high school anymore, except for. And on the other hand, we did have an incident back in high school where my partner's childhood best friend did get her younger sister pregnant.

[Host]

Your partner's childhood best friend getting your younger sister.

[Molly]

Okay.

[Host]

Did she have the baby?

[Molly]

She did have the baby. The baby has a great family. Her sister is doing great. She has a great life. She is married, has a great job. So everyone's lives turned out okay.

[Sally]

Okay.

[Host]

She married the guy or married a different guy?

[Molly]

She married a different guy.

[Sarah]

Okay.

[Host]

Are you still friends with this former best friend?

[Molly]

Yes. So we have maintained a friendship over the years to varying degrees. We, you know, didn't live in the same state for a long time, and then we did live in the same state, and now we live in different states again. So there's been varying degrees of closeness throughout the years, but we do still keep in touch.

[Host]

Are you ready to say goodbye to that friendship?

[Molly]

That is a great question and something I have been asking myself, and I think I go back and forth. This friend does have redeeming qualities. She is hilarious. Again, there's a lot of. There's a lot of history there because we've known each other for such a long time. I'm 31 now, and we met and became best friends our sophomore year of high school. So that's a lot of time that has passed. And I, you know, ideally would like to preserve the friendship, but I think I've reached a point where I'm just not sure that that's going to be possible.

[Host]

What do you think she's going to do if she comes to your wedding?

[Molly]

Part of the issue that I have with her is that she can be, you know, really abrasive, and at times, it's hard for her to essentially keep her mouth shut. So we've had some instances where even in front of my fiance. She has, you know, started saying negative things about his friends. It gets. In my opinion, it's very inappropriate. You know, she knows that they're good friends, and that's just not the time or place to talk bad about them. She's not going to change my fiance's mind about his friends, and I wish she would just keep it to herself and vent about that to someone else if she felt the need to do it. And so I do worry about her getting along with the people who are there. And she has said before that if she were in a room with my fiance's childhood best friend, she would find it difficult to keep her mouth shut and, you know, not say anything to his friend who got her sister pregnant.

[Host]

Is that. Is he still involved with his kid?

[Molly]

He is not. So the baby was adopted and lives in a different part of the country, and her sister just receives updates from time to time, but she's not really involved in the child's life either.

[Host]

Right.

[Molly]

But I think the issue was the. All the way back in high school, it was a very difficult situation. Of course, her sister was in denial, kind of lied about the situation, and then when she finally told this guy that she was pregnant about a month before she was due, he didn't handle it well.

[Host]

Okay, that makes sense. If there's any hope of not inviting her and still maintaining this friendship. And I get what you're saying. I get it. But there are people in this world who have thought I probably was abrasive. There's probably people in this world who thought that maybe I lacked tact in various moments. And I'm sure there are times in this lifetime where I've give my opinion about people at a time when it wasn't welcomed and not necessary and not helpful. And I can still, like, you know, recognize when a day is not about me. And we can all grow and evolve and yada, yada, yada. Which is all to say that uninviting her without. I mean, you're asked, like, how do I do it? And what do I say? Well, you know, you're gonna have to be honest with her. Are you willing to uninvite her and be honest with her without at least giving her a chance? And I guess by a chance by saying, listen, can I just. Can I. Can we talk? And I'm. I just want to be really honest with you. Like, I'm. I'm a little bit worried about inviting you to my wedding. Here's why. You've made it very clear about how you Feel about. Some people love you, but you can at least acknowledge that sometimes, you know, you like to keep it real, even when. And other people don't want you to keep it real. And there's parts of that I love about you, but, like, on this particular day, it's not. I need you to promise me you won't, because it's literally not about you. And I. I don't want to worry about any type of drama or conflict, you know, on my wedding day. And I. I feel like if you want to keep this person in your life as a friend, she deserves an opportunity to at least hear that, you know, and. And to say. She could say, well, that would be really difficult for me. You could be like, well, then maybe you should just sit when this one out. I won't be offended if you don't. Or she could be like, listen, I. You know, the. The correct response will be like, listen, I. I get. I put my phone in mouth. I understand sometimes, blah, blah. But like, listen, I hope that you know that, like, I'm just here to celebrate you in your marriage. And I'm just. That's, you know, that's. That's my only, like, that is. That's the correct response. And I. If she can't do that, then maybe you shouldn't be friends with this girl. But I just wonder if maybe she can be invited and you can just talk to her about your concerns and she could just be normal. You know what I'm saying? Is that possible? Do you see. You know, do you. Do you think there. That there's a lane there?

[Molly]

That is a great question. And that's something that I have wondered myself. I think at times I've been so scared of the fallout, and she is very confrontational. I am not confrontational. And I've sometimes worried that saying something might not be worth it, because I have wondered if it would do any good. But I have wondered that if, you know, she is my friend, does she and I consider her a good friend, does she at least deserve the opportunity to hear the truth and hear my feelings and have the opportunity to react correctly?

[Host]

Yeah, well, listen, I. I say this as someone who's comfortable with conflict in the way that your friend is. And I. And I also acknowledge that your wedding day is not a day to. To with. So to speak. But on the other side, I think this is an opportunity for you to have a conversation that makes you a little uncomfortable, that you certainly can survive, and she's not going to hurt you. It just might be a little uncomfortable for you. And I think that's probably worth having. You don't know how the conversation is going to go, but you can certainly survive it. And that might. And the willingness to have that conversation, there's a good chance that's the solution because you do have reason on your side. And unless she is just full on, I mean, like, I guess my point is like saying, do you really want to be with someone who can't possibly get out of her own? Like then, then you're talking about someone who's just incredibly self centered and selfish, you know, because for example, like when I was like, I've, you know, I've been that person, blah, blah, blah. And like every once in a while you're just like, you're around a group of people, you decide to be a little messy and you speak up, but it's just like another Saturday night and like whatever. And your friend clearly is comfortable with some people not liking her, at least to a certain extent and whatever. But on any Saturday night it's not about her. And I, again, if, if she's so self centered and so selfish that like on someone else's wedding she can't just let bygones be guy bygones and, and you know, when she's like, oh, I, if I saw them, I've had a hard time not saying anything. Well, that's fair. You can say that. That's, you know, whatever, your choice. But like, what if it's literally not about you on this particular day? You know what, like, would you like, is there any situation in which you couldn't keep your mouth shut? You know, like, you know, you know what I'm saying? Like, is she that unreasonable? There's also just, I will say something and I don't know, you've probably heard me talk about weddings before, but I think people underestimate the value of a little drama and a good story at a wedding. Because your job on your wedding day is to not care about any of these people.

[Molly]

True.

[Host]

It's not your responsibility to focus your energy if they're having a good time. You obviously are going through some wedding planning. I'm sure it's stressful as fuck as it is for everyone dealing. You're putting in the work now to plan the party for your guests to have a good time to celebrate you and your future husband. But on that particular day, I truly hope for you and your husband that you guys are so connected that you're really just not worrying, like they're, you know, shit will be happening that you're gonna hear about later, you know, and it's all. It's all makes for a good story, because how you feel about your wedding day is gonna be the experience you feel with your partner. And I do think sometimes some good drama makes for a good. Like, it makes for some good memories. There was a little bit of drama at our wedding. It did not stop it from being an incredible wedding.

[Molly]

Those are all very good points. And I agree. When I am at weddings or I don't attend weddings, but I, you know, ask other guests, you know, was there any drama? Like, it's always fun to hear, you know, what's happening behind the scenes.

[Sally]

Yeah.

[Host]

It doesn't ruin the wedding. The only thing that's gonna ruin your wedding is not feeling connected to your partner. And the only thing that's gonna. You know, the only part of this story that's gonna stop that is if you have your energy focused in the wrong direction. If you wake up worrying about what's Mandy gonna say to Eric, you know, so it's just like. But you shouldn't give a fuck. You know? That being said, it is definitely worthy of a conversation with your friend. And you have a right to ask all your guests to just, like, not make that today about them. But for someone who's not comfortable with conflict, I honestly think the easier choice is to have this conversation to try than to just be like, you're not invited, because I think you're crazy and selfish.

[Molly]

That is fair. Yes. And I think that is a good point to at least give the opportunity to see what she says before, you know, taking the. The most dramatic option.

[Host]

Yeah. And then, you know, you could. You could talk to her. She could be like, no, for sure. And then the wedding day could happen, and she could not do the things she promised not to do. But that's. That's a. You know, then you can just deal with that. It still won't impact your wedding. You know, I don't. I mean, do you mean she. Is she gonna make a scene? Is she a big drinker? Like, is it gonna get so bad that, like, the. The wedding stops?

[Molly]

I don't think so. I don't think that would happen. I think I'm a little bit nervous because it is going to be like a micro wedding. Like, there will be, like, 10 to 15 people there. And so there's just less of a buffer.

[Host]

That's an element. You didn't meant.

[Sally]

That's a.

[Host]

That's. That's fair. That's different. That's A little different.

[Molly]

So I would worry less if it was a big wedding and there was going to be a lot of people there to buffer. I think I would be a lot less worried about this. But I think because there's going to be so few people there, it just increases the opportunity that she's going to have to interact with people. That's.

[Host]

That's fair. That's a good point. Yeah, that does make it tougher. I still think the advice still stands that, like, listen, if you can't have this conversation, what's the point of being friends with this person if you have that little faith in her? And if she can't get out of her own goddamn way for one afternoon, then it's just. And as a friend, as someone who, you know, I don't think I've ever been this bad. I don't think anyone's been that worried about me. Like, you're worried about your friend. But as someone who, you know, can be a little unafraid of conflict and a little, like, sometimes, you know, I've been that. Certainly in my younger years, I would have appreciated the opportunity to be like, listen, I know I can be that way, but, like, please have a little faith in me that I'm not a total disaster. Was she curious as why she. She were. She was not included in the bachelorette party.

[Molly]

So it wasn't that she wasn't included in the bachelorette party when I. I ended up telling her in a text message that I was engaged because I actually wasn't sure that she would have the best reaction to me telling her I was engaged. So when I told her a long time ago, now that I was dating my fiance, she, because she was so upset about my fiance's attachment to this guy from our past, she is single and she sometimes has a hard time getting out of her own way to be, like, happy for other people. And so I did not tell her she wasn't a friend that I FaceTimed and was like, oh, my gosh, guess what? You know, my fiance proposed. I told her in a text message. And when I sent her this text message in a group text, she, the other person in the group text already knew that was a friend who I have FaceTime to be like, oh, my gosh, I'm engaged. She immediately messaged me one on one and said, hey, I want to plan your bachelorette. Because I wasn't able to plan so and so's bachelorette because I was poor and living in a different city at the time. And this will be my one chance to plan a bachelorette. So I really want to plan it. And also, your sister in law is not invited.

[Host]

That's crazy.

[Molly]

And it is a little crazy.

[Host]

What did you respond with? Because it's funny, because it's. I mean, I imagine her. The initial response was surprising that she was positive about the engagement and then hit you with the. But I'm still not over it.

[Molly]

Yes. So she. I just responded and I said, you know, thank you for offering. That is very nice. I just got engaged. I don't have any plans for anything right now. So if, you know, I decide even to have a bachelorette, I will keep you posted. And she's brought it up a few times and I've just tried to put it off because at this bachelorette, I might want to include the wives and girlfriends of some of those people that my fiance is friends with. And I don't know that she would be okay with that. She had kind of said like, hey, wouldn't it be fun if your bachelorette was just me and our one other friend that I like? And no, you know, I don't think that would be fun. And so I've. Someone tossed out the idea that I could have two bachelorettes.

[Host]

That's crazy.

[Molly]

A normal. Yeah, it's just getting a little crazy.

[Host]

You need to have this conversation with your friend because she is way too comfortable suggesting crazy shit. And there's no way she hasn't gotten this comfortable without knowing either consciously or subconsciously that you don't actually push back. You just kind of avoid.

[Molly]

That's a really good point.

[Host]

You know, you're just kind of like, she's never heard how crazy she is and just like, yo, at least not for me. So you just need to do it in a way that is upfront, honest, but not mean. You know, you're just like, yo, come on. Like, you can't. Maybe you were kidding, but like, if to whatever degree you weren't kidding, like, I can't. You can't ask. Not to exclude. I'm getting married to this person. I hope it goes without saying that this is the most important person in my life. And with that comes like, listen, you've been one of my closest friends for a really long time and that's a friendship I want to still matter. But we are adults now and I can't keep holding on to shit you haven't let go. And I'm not telling you to get over stuff, but again, I just want to be up front, like, I'm having a really small wedding. A lot of people aren't invited. And you've made it very clear how you feel about these people. And I am not telling you to get over it, but, like, this is my day, and I'm just need to ask you if. If you can, like, check yourself on my day. And I'm not here to silence you, but if you can't promise me that I can't have you come to the wedding. And that's a very reasonable conversation that, like, I think you just. You, as a person who can acknowledge you're not good with conflict, needs. Needs to have that. It will. It will be like, this is more about that to me. For my advice is coming from a. You can do this. You need to be good at doing this. It is a life skill. If you're so bad at conflict to the point you let people in your life get comfortable with saying crazy to you, that is not. Not. That's not good for you.

[Molly]

Yeah, no, I think. I think you're exactly right. And again, I think that I've just established some really bad habits in this relationship because we have been friends for so long. Right. I did not meet this person in my adulthood when I was kind of better at setting boundaries. I met this person when I was really young and in high school. And I, you know, really didn't know how to handle conflicts and really didn't know how to set boundaries back then. And I think I just established some bad habits that I never addressed or fixed. And now it's really, like, coming to a head, and I do need to say something.

[Host]

I think. Yeah, there we go. We have a good plan. So that way, you know, maybe she's. Maybe she's invited, maybe she's not invited. But I have the conversation first and then. And then decide because, like, just.

[Molly]

Okay, I think. I think that's fair.

[Host]

Okay. All right, cool. Well, I'm dying to know how this

[Molly]

goes, so thank you. I appreciate. I appreciate the advice. I think that is really, like, a good middle ground of, you know, letting everything kind of rest on her shoulders and how she reacts to just me bringing up some very honest feelings and concerns that I have.

[Host]

Yeah. You know, listen, she's valid to feel how she feels. As a friend, you would suggest to maybe be more like, listen, a lot of time has passed. We are. None of us are the same person as high school. So, like. And I'm not telling you how, you know, to let things go, obviously, like, this was a traumatic time in your family's life, but. And I Want to respect that, but this is not your day. And. And you can say to some level it was a little concerning, and maybe you were joking, but I honestly don't think you were. That. You tried to make my. You made my batch. My. My potential bachelorette. More about you and your comforts and what you wanted or what you didn't want than about me. And that's just not how my wedding's gonna go.

[Molly]

Yeah, I think that's all fair.

[Host]

Worry less about how she's gonna react and really see this as an opportunity to feel good about, you know, speaking your mind with someone you really haven't spoken your mind to. Hopefully it feels empowering for you.

[Molly]

Well, thank you. I think that's a really good way to look at it. And I think you're right. I've kind of let this relationship go far too long without setting boundaries and being able to tell her how I feel. And in good friendships, you should be able to tell them how you feel. And so this will be a good test. I don't. Well, not necessarily test. I don't like that word, but just like a good barometer of, you know, is this someone who's going to be caring about my feelings or not?

[Host]

Yeah, because, you know, you're 31, and you already, I'm sure, have known this, but as you move in this part of your life and you're. You don't have time for relationships in your life that no longer serve you, and you care less and less about relationships existing because of how they started and more about, like, what they do for you today. And so she needs to show up as your friend today and not. Not. It's. It's. You know, we were friends in high school. Doesn't get you very far these days, and you'll. You'll just. It's just not worth your time or energy.

[Molly]

I think that's true. Thank you.

[Host]

All right, well, please give us an update if you have one to give.

[Molly]

I will for sure. I will keep you posted.

[Host]

When's the big day?

[Molly]

We. We are going to have a long engagement, so we are thinking September of next year.

[Host]

Awesome. Cool. Don't put off this conversation more than you need to. Don't let your long engagement extend it, you know?

[Molly]

Yes, I agree. I would rather stop worrying about it, especially as I'm in the planning process and thinking about who's going to be there and how many people, you know, we need to accommodate for. Think it would be. Take some stress off of my shoulders just to have this conversation and you know, get things figured out.

[Host]

Just out of curiosity, why does she blame the entire friend group for something that happened with her sister?

[Molly]

I, I think it's, I think it's a mix of things. I think she doesn't like that one guy because of what happened with her sister. And for the rest of the people, a lot of her insecurities are rearing their heads when she, I think for the rest of the people, she says, you know, I don't like those people because I feel like they didn't like me in high school and they still see me as I was in high school. And I think what's actually happening is she still has some leftover insecurities and she might still see herself to some degree as she was in high school. Because in my opinion, if she had really changed and you know, felt confident she wouldn't care about what anyone thought of her in high school because she could be like, yeah, I'm a different person now.

[Host]

Or maybe she's not. Or maybe she was a pain in the ass then and she's a pain

[Announcer]

in the ass today.

[Molly]

I, I think that I, I don't want to admit to myself maybe that that's true, but just with the way things are going, I think that might very well be the case.

[Host]

Well, you know, I've been a pain in the ass. I can be a pain in the ass. I will say the pain like they can also grow and change and it sometimes takes a good friend to have a tough conversation to just say, listen, you're like, you just don't. You, you can let you know you don't like. You can pick and choose your battles.

[Molly]

Really good advice.

[Host]

All right, well, good luck. Keep us posted.

[Molly]

Thank you. I appreciate it. Have a good one.

[Host]

You too. Bye bye. What's up everybody? Don't forget that all Vile Files plus content is ad free. Plus for all you ask Nick listeners out there, your update specials are ready and waiting for you. I know you are very interested on the follow up calls. What has happened to these people after they heard my advice? Did it help them? Did it hurt them? Has their life changed? Well, you can find out on update plus and you can get update plus behind vile files plus. So go to vilefiles.com to sign up. You will be glad that you did. Furnishing your home can feel overwhelming and that's why people love article. They love it because it's simple and has everything you could possibly need to furnish your entire home. Any room that you want, indoor or an outdoor. They have you covered? Article offers thoughtful curated collection inspired by mid century modern, coastal and Scandinavian design. Their pieces are designed cohesively so it's easy to mix and match. Every piece is built for craftsmanship, design and long term value. No filler, no throwaway furniture. And I can speak to that. We have articles furniture that we've had for going on three or four years now. It's incredibly great condition. Even it's sitting outside in the hot intense sun in la. But doesn't matter. It's made with love and and just quality. But the prices you can't beat because they cut out the middleman. And also what I love about article is they have stuff in shock too. Many times we've bought furniture other places where you have to wait so long for the furniture and it's frustrating. Not with article. Most of the pieces are ready to ship for you when you order it. Article's customer care team is also available seven days a week and even helps advise with complimentary interior design services. Article offers a 30 day satisfaction guarantees to help ensure that you will absolutely be in love with your furniture. And if for some reason you're not, they make the whole return and exchange process incredibly easy and pain free. Article is offering our listeners 50 off your first purchase of 100 or more. To claim, visit article.comvill and the discount will be automatically applied at checkout. That's article.comvill off your first purchase of $100 or more. How's it going?

[Sarah]

Good. How are you?

[Host]

Good. What's your name?

[Sarah]

My name is Sarah. I am 31 and my question is, is it confident or desperate to reach out again to a guy who left you on red after saying you want to have sex with him?

[Host]

It's definitely more desperate than confident. Forget about what it looks like to anyone else. Like why, why are you wanting to reach out after this person has left you on red? Are they like, is it the sex? Is it that good?

[Sarah]

It's fine.

[Host]

It's fine.

[Sarah]

So backstory is, although he left me on red after I. I sent him that text.

[Host]

What was the text then?

[Sarah]

We have communicated after. So he's just ignoring me on that front, which I find very annoying.

[Host]

All right, so tell me, give me the, give me the context of this relationship. Give me the, give me the one minute version story of this relationship.

[Sarah]

Yeah. Long story short, we went to school together, we worked together, we hooked up on and off for years. Back in the day.

[Host]

Back in the day when, When Back

[Sarah]

in the day, the last time I saw him before the recent hookup was eight and a half years ago.

[Host]

Okay.

[Sarah]

After that go around, I had shot my shot with him and he rejected me.

[Host]

How long ago was that?

[Sarah]

In a nice way, I'll give him that. I said I wanted more than just a hookup, and he said, no, thanks. So we went our separate ways. No harm, no foul. He ended up getting married, having kids, the whole nine. I live in a different city now, so I didn't think about him again for the longest time. And then two Christmases ago, he DMed me after I posted about my cat dying on Christmas. I'm sorry. Thanks. It's, you know, it happens. And we just chatted a little bit, and he kind of was like, oh, well, turns out he was getting divorced and having a bad time as well, so obviously wanted someone to, you know, commiserate with. And at that time, I was kind of like, good for you. It's been way too long. I'm over it. And then, you know, I was dating somebody else. After that didn't work out. He seemed like an easy option to have some fun with. So we started chatting again, flirting back and forth, and then we just could never make a time work since we live in different cities. Two months ago, I was home visiting my parents. He still lives in our hometown. And I just messaged him, was like, hey, are you free for a drink tonight? He said, yes. We got together, we hooked up, we're getting there. And then he finishes very prematurely and was embarrassed about it. And I did everything I could to make him not be embarrassed about it. It happens, obviously. But we ended the night after that, and then I sent him a text the next day that was related to something we had talked about and was like, so are we gonna do this again? And then he was like, I don't know if I want to embarrass myself again, was the text. So my text to him was, okay, well, if it's not abundantly clear, I want to have sex with you again. So he did not respond to that text message. And then I responded to something else related to sports, and we kind of went back and forth about that. And then I texted him, happy birthday. He said, thanks, and that's where we're at now. I never responded to the thank you.

[Host]

There's nothing to respond to.

[Sarah]

What's the point?

[Host]

What would you want him to do if you were in his shoes? And vice versa. So you're him. He's you. I mean, let's say forget about the finishing fast or whatever, but sure, what would cause you to not reply to a. A proposition of sex via text. Like, what do you think? I mean, what's the simplest answer to that question?

[Sarah]

That he doesn't want to, obviously.

[Host]

No. No. Well, yeah, maybe you don't want to. Or maybe, like. Yeah, but even the why you don't. Maybe you don't even know why you want to. You know, or you don't know what to respond with. So to answer your question, like, is it confident or is it desperate? Would you want someone to follow up? Let's say you just didn't know what to say. You know, Would you want a guy to pressure you to have sex?

[Sarah]

No. Obviously.

[Host]

And what would him asking again without you replying feel a little bit like, pressure?

[Sarah]

I don't think that I should ask him again to have sex with me, to be fair.

[Host]

Fair, okay.

[Sarah]

But I would like to get together with him again and just kind of get over the embarrassment.

[Host]

Wow.

[Sarah]

But I realize I can't, like, force someone to. To do that.

[Host]

The way to get over the embarrassment is to not make it a thing fair to not have to meet for coffee to get over it.

[Sarah]

That's fair.

[Host]

Maybe he was literally busy. Maybe he was in the middle of something. I know. We just always assume because we're on our phone so much that everyone else is just sitting there waiting for our texts, but he could have been in the middle of something and then Simon. And also just. Also, he could have just been like, I don't. I don't know, man. I don't know what the. How do you. How do you text back? No. And, yeah, I mean, like, maybe he just was more like.

[Sarah]

I don't know.

[Host]

Like, I just. You guys have done this already multiple times. It's like, what's the point? How old are you again?

[Sarah]

I'm 31. He's 33.

[Host]

Yeah. So, like, you guys are certainly old enough to know, like, you guys have gotten laid before, so it's not like you're young and horny and there's clearly, like, some kind of friendship here. He's already turned you down romantically in the past, and it sounds like your goal is to get over the awkwardness so that maybe it could happen again.

[Sarah]

Yes.

[Host]

And I think, yeah, I guess that's what. That's the part you should. And again, just, you're not a guy, and he's not a woman. I'm not. And I don't think those dynamics are always equal. Nevertheless, I do think it is fair to just point out that if the roles were Reverse. It would come across differently if it was like him trying to figure out how to sit down and have a conversation with you so that he could keep having sex with you even if you didn't want to have sex with him.

[Sarah]

That is fair.

[Host]

And then maybe it's just better, better, better to let it go.

[Sarah]

Yeah.

[Host]

And you guys have already hooked up and chances are like. And forgetting about that, this easiest way to make a non awkward situation not awkward is to not make it a thing. And you're trying to figure out how to make it a thing without making the thing. And that makes it a thing.

[Sarah]

Yeah.

[Host]

You know, and you're kind of in your head about it and you're kind of, you're. There's a little bit of like, correct me if I'm wrong, but you're like, oh, he finished fast. So I'm worried that he's in his head. But like, I bet you, I bet you're in your head too about what he thinks about why that whole experience went the way it did. And this is more about just making sure he's okay. You're trying to make, you're like, you want to make sure you're good too.

[Sarah]

Yeah. Fair. What I find frustrating is that I do not like, generally participate in hookup culture. I am a pretty risk averse person, so I realize that. Sure. Can I, like, go out and find somebody else? I guess. But like, I would selfishly like an easy summer hookup. I obviously can't, like you said, force someone to be interested in that situation either.

[Host]

Well, it sounds like maybe you just kind of. You've always had a crush on this guy and it's just you haven't landed that plane.

[Sarah]

Yes. And I, I think at this stage in our lives, to be fair, I think we're in such different places that it, it just literally couldn't go any farther than.

[Host]

Yeah, but you say that maybe the objective person in you is saying that out loud because you recognize the truth. But the hopeful person or whatever in you is trying, you're trying to do the thing that many of us and we've all do is to convince yourself that you're seeing this with a level head by acknowledging most or part of the truth, but then doing the mental gymnastics to try to convince yourself how to still kind of also at least get some version of what you want and calling it something different like you're calling it. I just want to. I just want a casual summer hang fling, right? No, you want to have sex with a guy. You kind of like, even though you acknowledge that maybe at this stage in the game that ship has sailed.

[Sarah]

Right.

[Host]

And you're hoping the part of you that says it's not practical or probably not possible, you're hoping that part's wrong. And you want to get yourself into this hookup situation with this guy in hopes that you're wrong.

[Sarah]

Yeah. So do I just, I guess, leave it alone and.

[Host]

Yeah, yeah.

[Sarah]

Move on. I mean, I don't really think there's anything to move on from other than,

[Host]

you know, you're probably right. And that's a good thing. The good news is this is not something you need to get over. You're not like obsessed with this guy. I just think it's just more you're. Yeah. You're just kind of creating a scenario that doesn't really exist. And listen, there's a good chance you'll hook up with him again.

[Sally]

I don't know.

[Host]

But like, not right now. But I also think like, it's just gen. He's genuinely. He's generally a waste of your time because you're probably not wrong. He's probably not your future. If you really just want a summer hookup, you can find one. It might take a little bit of work. Also, like, if the sex is just fine, then why like. And I'm not saying yeah, I mean sex was. But you can be genuinely not a risk taker. You can practice safe sex. You know, there's no guarantee, but you can be, you can still, you can. You don't have to be a risky person to participate in this hookup culture. I understand that by nature it's generally riskier than not, but I think you can prioritize safety still.

[Sarah]

Yeah, I guess I just, I meant more of like an emotional risk, I suppose, which I guess there is one. There you go here in, in your point that, you know.

[Host]

Well, there's more of an emotional risk here than, than. Than having sex with a person. You didn't this make believe at this point. And yeah, I think it's always risky for people to. Even for men, but especially for women, just because biologically how our bodies respond differently to sex is that, you know, there is the. We can, we can say all we want that we're not emotionally connected to people and it's just, it's just sex, but it often is not just sexual. Right.

[Sarah]

And I guess I was thinking of it in, in such a way that like I don't need. Need to. Need to deal with that for. With a straight stranger to your point. But I Guess it's not, it's not any better to do it with someone you already have that, that connection with. To be fair, I just have a hard, hard time prioritizing dating and meeting people in general. I, I lead a fairly active, busy life. So I was again selfishly hoping for,

[Host]

you know, how active and how busy.

[Sarah]

I'm an attorney, so I travel a lot for work to court and different cities for trials and arguments and things like that.

[Host]

So what kind of law do you practice?

[Sarah]

I do appellate law, which is convoluted, but essentially it's the next level of after a trial happens or a decision is made by a court or a jury that somebody doesn't like, you come

[Host]

in and you're looking for other people's mistakes.

[Sarah]

Yes.

[Host]

Yeah.

[Sarah]

And try to fix them.

[Host]

Do you like it?

[Sarah]

It's a fun job. I really enjoy my co workers, they're the best. And I enjoy traveling and meeting new people and seeing new places and practicing.

[Host]

Yeah, I mean, you know, I was curious what you would say, but it sounds like that's pretty time consuming. I imagine that could make dating more difficult.

[Sarah]

So, you know, I mean, I do date and I go out and I meet people when I'm home. I have a harder time meeting, not that I couldn't, but a harder time meeting people while traveling just because I'm generally speaking in court all day and then I have to report and things like that afterwards. So that, that is more or less half of my month. And then when I'm home, if I go out on a date or two, there's nothing wrong with the guys. It's just like they don't capture my attention enough to want to see them longer than the hour or two that we get together for a coffee or a drink or whatever. And if I do want to see

[Host]

them, well, to be honest, if you are just looking for summer sex, you want the person who you don't aren't captivated by the opposite.

[Sarah]

Problem in my head with that is I can't seem to find any sort of excitement about that. And personally I feel I have to have some sort of attraction or.

[Host]

That makes sense.

[Sarah]

Looking forward to getting.

[Host]

That's the paradox, I suppose.

[Sarah]

Yeah. I don't usually find it worthwhile to go through the effort of getting naked with someone if I'm not excited about it and all of the, again like risk factor that comes with it. So I obviously am a fairly logical borderline.

[Host]

Is it really the sex that that's important?

[Sarah]

No, no, it's.

[Host]

It's the Companionship.

[Sarah]

With the original guy, it was just. That was an easy avenue to get in there. That is not to say that, like, listen, not to be crass, but, like, you know, I can most of the time do it better myself. Sometimes, though, you want a partner, so.

[Host]

Yeah, I hear you. You know, I totally get it. But. But I also. I guess what I'm saying is, to that point, knowing that, like, five burgers exist and shit, and is that, like, it's really just the companionship. I mean, this whole conversation has been like summer hookups and, like, about the sex and a. I think if you just take sex off the table with this guy, don't make it a thing. I'm sure he'll reach out again. Sounds like you're already still talking.

[Sarah]

Yeah.

[Host]

And I would just let that go. And the thing that you're maybe, like, wanting the most when it comes to is companionship. I mean, the sex, Gray, that's like, you know, who doesn't want to have some occasional sex if it's on the table?

[Sarah]

Right.

[Host]

But when you're. When you're talking about intimacy, you're not focused on the physical aspect of it.

[Sarah]

Right.

[Host]

Which is, I think, something you should note that it's not the sex that you're looking for as much as the companionship.

[Sarah]

For sure. And as you, I'm sure, know, the. That is the hard, hard thing to find. Right. Especially if you have, I don't know, high standards or too high standards, whatever you want to call them. Of. Of. I sometimes think that I can come off rather, again, like, cold and too logical for a lot of men. But I. I very strongly believe that, you know, I don't. I don't need to be in a relationship with someone unless they enhance my life. Like, I have a pretty solid, good, exciting life all by myself.

[Host]

Yeah. As far as this guy goes, I would let that shit go, especially the sex part. I think you should take sex with this guy off the table. It doesn't seem like it's. It sounds like what you described, which is like, someone you're comfortable having sex with. And it's nice to have sex every once in a while.

[Sarah]

Right.

[Host]

But it also sounds like it makes a relationship with the person you like are comfortable with more awkward. And it sounds like you do enjoy his company.

[Sarah]

Yeah.

[Host]

Yeah. No. Yeah.

[Sarah]

I mean, yes, I think we would be friends if we were in the same place. We're just not in the same city. So. Not that I couldn't reach out or he couldn't reach out, but I Can't say that I post about when I'm home or that I'm really home visiting my parents all that often for anything other than a specific purpose. So I don't have a ton of free time to just be like, hey, or he can't necessarily see, hey, I'm in town. So it would have, like, if I were to be. Develop a friendship with him at this point.

[Host]

But let me ask you this. Like, the last time, I don't know, you hooked up, what did you enjoy most? The sex or the time leading up to it?

[Sarah]

I enjoyed the anticipation of what was to come, but I knew that was to come with him. That's the, I guess, disconnect of meeting random people on a dating app or out in the wild or whatever for a date is that I can't say that I've like, felt that excitement or that anticipation with them, any person in a really long time.

[Host]

But the excitement that you guys were gonna have sex that night.

[Sarah]

Right.

[Host]

What was the last time you slept with someone else?

[Sarah]

It's been years. Not necessarily. I. The last time was not with this man, but like, I haven't slept with anybody in several years other than this guy.

[Host]

Okay. And why? By choice, obviously.

[Sarah]

Yeah. For a long time while I was in law school and then starting practice, I just actively did not have time. I was working in school and just didn't care to foster any of those signals that may or may not have existed. And then the pandemic hit, so I was stuck home and I lived with people at the time, so I wasn't inviting strangers into my house or going to their house. That is not something I'm interested in, that wasn't interested in during that time. So, yeah, it's just been like post, post pandemic that I've been actively dating and out there and lollygagging while dating, but I just this. I just haven't been interested enough in somebody to want to get naked with them.

[Host]

But what do you think's the difference between him and them?

[Sarah]

I just know that, like, I've already done it with him before. I'm comfortable with him and like, it's. It's easy. Okay. But I guess, like, even though there's the. I just say even though there's like the, I guess, embarrassment factor or whatever currently, I mean, I don't. I'm not embarrassed. I couldn't. I don't.

[Host]

I get it. Yeah.

[Sarah]

Either way. But not that it was an expectation, but there was enough of a history there to know that the night Was going to lead there. Right. I don't. Generally, I haven't had that interest or excitement or anticipation with any guy I've dated or gone out with on random dates or met out in the wild, like I said, in the last several years.

[Host]

But you. You kind of admit you kind of have a crush on him or you did, right?

[Announcer]

Like, you.

[Sarah]

Sure, yeah. Yeah.

[Host]

Okay. So that obviously seems to play a role. Do you have any insecurities or fears about, like, putting yourself out there with other men or, like, fear of rejection or anything like that?

[Sarah]

I don't think that I have a fear of rejection. I tend to be more challenging to, I guess, like, open, not open up. Like, I'm a pretty open book. But to be fair, I'm having a hard time, like, figuring out how to articulate what I'm looking for in a partner, which is why dating is challenging. Like, I'm not. It's not a priority for me to get married. I do not want to create my own children. I would like to adopt children. So there's not like a time crunch biologically to kind of get any of these things rolling.

[Host]

Are you looking for, like, a boyfriend? Would you like a boyfriend?

[Sarah]

I would like a partner. I don't want a boyfriend.

[Host]

I mean, we're getting into semantics, but, yes, I would. Yeah, a partner is definitely better. I mean, a boyfriend is just a label, right? A partner is a description of hopefully something you have and a. Like a partnership type of thing. But, like, that's a semantics. Are you looking for a committed relationship? Ideally, by looking, I don't. I don't mean. I don't mean like you're desperate. I just mean, like, is that something that you are open and wanting?

[Sarah]

Yeah, I think that's the goal with. Well, that is my goal with dating. Great.

[Host]

So that's good that you know the goal, because oftentimes people don't know the goal, but you're off. You're also, like, I would put you in another really large bucket. Is that despite your goal, you're doing things that, like, kind of go against your stated goal. And we've been talking for 33 minutes, and this is the first time you've said, hey, I just want to make it clear, like, what my dating goal is. The goal that you kind of led with is a summer hookup.

[Sarah]

Right.

[Host]

Or to get to this. This guy who you've stated isn't your guy to have sex with you again. So I. And you're busy and you're, you know, you have this very incredibly Demanding profession, and your time is limited. So in your limited time, my general advice to you is to do things in the dating space in your very limited time that help you get to your goal. The only part about that is it's a little scary because sometimes there is the fear of failure and there's the fear of rejection. And it can be scary to be intentional, because by definition, you're doing something that is trying to lead to something that you want. And then along that journey and that path, there's always ups and downs. And that's why I asked the question, is there any fear or insecurities around dating or finding your person? Because sometimes when we have a goal, we're doing things that kind of go against that. It's mostly based off of that fear of failure, that fear of rejection. So I would just be mindful about. You're a very busy, accomplished person with a limited time. And while you're young, the easiest way to get to a place where you are not as young as you used to be, but still haven't met your goal is to do things that don't help you meet your goal. Because time does fly. And there's a lot of people who do things that aren't doing that, helping them meet their goal. And that's when you wake up and you're 45 and you're like, not where I want to be.

[Sarah]

Right.

[Host]

But the good news is you're only 31.

[Molly]

No.

[Sarah]

Yeah, like I said, I'm not in any rush because it's not necessarily the priority.

[Host]

But not in a rush is not an excuse not to be intentional with how you move as it relates to your dating goals.

[Sarah]

Yeah, I guess.

[Host]

And sometimes we say I'm not in a rush as an excuse to, like, not do things that match our goal.

[Sarah]

Right? Yeah, I guess. Like, the summer hookup idea with this particular guy was just an more or less an easy break. Right. From dating. The time that I would be spent, I would spend otherwise dating would. Would be utilized for that purpose.

[Host]

What purpose?

[Sarah]

Just to see that other guy.

[Host]

But as you said, you mean you're. Most of the time, you're better at doing it yourself. So in terms of the. Any meaningful moments you spend with his guys, technically, by definition, a waste of your time.

[Sarah]

Right.

[Host]

I think there's a part of you that doesn't want to believe that. True.

[Sarah]

Yeah. Well, sure, nobody wants to waste their

[Host]

time, but no one wants to waste their time. But that's what I'm talking about. I think you. You've acknowledged there's a bit of a crush here. And I think you say that. I don't think. I think that ship has sailed. But there's the hope that it hasn't.

[Sarah]

Right.

[Host]

And if you are going to pursue this guy, I don't know if you necessarily should, you might as well at least be honest with yourself that that's what you want, rather than tell yourself, I just want a summer fling.

[Sarah]

Right. I'm sure you know from talking to 800 people all the time that, you know, dating is hard and sometimes, sometimes you just want the easy, the easy way out.

[Host]

I hear you, I hear you. But when was the last time you really put yourself out there?

[Sarah]

I mean, I was in the midst of all this. I've dated, gone on dates with other people. I am 90% of the time the one who asks them out the first time, which, you know, is fine.

[Host]

I hear you. Not ideal.

[Sarah]

I try really hard not to think about dating as a chore. Right. Or like another a to do list check off box, because I don't, I don't need to feel that way again. The goal is not to just find an okay person to get married and have kids with. So challenging to get excited about those, those people who, you know, dating obviously is a numbers game, but, you know, I don't want to get so bored of it that it, it becomes boring. You know, I have no problem meeting new people and talking to new people. And that's kind of the. I don't know where the difference is, but I have, I have plenty of new women friends that I've made in the last year that I'm excited to see and hang out with and, and go to coffee with or go to dinner with. And I, A lot of the men that I've. I've gone out with, I just, you know, after 1, 2, 3, 4 dates, I'm like, you know, there's nothing wrong with you. I just, I. If I never talk to you again, it would be fine. Which I usually tend to make the sign that it's not somebody I need to spend my time prioritizing.

[Host]

Yeah. But that is definitely, you know, normal.

[Sarah]

For sure. For sure. Yeah. So it's just, it's just one of. I think it's just one of those times. Well, it's not just one of those times. It's been years. Obviously there's been no one who I've been excited to commit to, and that can be draining.

[Host]

Outside of this guy, when was the last time that you, like, what was the most you've Spent time with someone.

[Sarah]

I mean, I've, like, you know, kissed a date or whatever, but nothing more than that. It's. I have yet to feel excited enough to want to take it home. So that also, again, to me, feels like enough of a. Not that you can't. You know, I don't necessarily believe that the spark is instantaneous. Like, I think you grow feelings of love and things like that, But I

[Host]

think in general, after talking to you, I can't say this for sure because I haven't talked to you for that long, but I get to get a sense that you need to put yourself out there a little bit more than you are. And I think maybe sometimes you hide behind the. I mean, I don't. You. Your job sounds incredibly busy, but busy, busy people can make time for things they want to do. So I would maybe just put yourself out a little bit more. And at the. At the risk of getting rejected by someone you might be interested in.

[Sarah]

Right.

[Host]

Because you will definitely survive that. It's just a little bit of an ego bruise.

[Sarah]

Yeah. Yeah.

[Host]

There's a difference between, like, being generally interested enough with someone to, like. If you're. If you're interested enough to have sex with this guy, then I don't know. You know, it's like. It's not like you're. I need to be in love with someone to date them, you know, and it sounds like you're just not putting yourself out there enough to get to know someone enough. Like you've gotten to know this guy and you're just. You're just comfortable with him just because of. Time has passed for sure. So I would just. I would try to put yourself out there a little bit more. And then as far as this guy goes, it just sounds like you should just, you know, stop. Stop having sex with him.

[Sarah]

I mean, fair. You know, it's not that challenging.

[Host]

And if he. If he was like. And if he's like, yo, like, let's go, and you're. And you're still down, go for it. But I would. I would stop trying to make him feel okay about it. I'm sure he feels fine about it.

[Sarah]

Right.

[Host]

He just.

[Sarah]

Not.

[Host]

He just might not be down.

[Sarah]

Yeah. Nor does he have to be.

[Host]

It's, you know, I mean, yeah, I don't know who this guy is and how he moves, but generally speaking, like, they never end well, you know, these casual hookups. And maybe he's just old enough to be like, I just don't need to do that with her. I don't wanna I don't. And maybe this last instant, like, what? You know, I don't think it's the end of the world. Some guy climaxes a little too quickly, whatever, like, but maybe it was just slightly awkward enough to be like, I don't know, maybe we should just not do that.

[Sarah]

Right?

[Host]

But yeah, I don't think it requires a sit down and a cup of coffee to let him know that he doesn't need to feel, you know, like just, it's totally fine. Just let it go, okay? Pretend it didn't happen. If he wants to bring it up, by all means. But there in the meantime, you know, just get out there. Challenge yourself to put yourself out there, maybe to go on a few more dates, maybe go on another date with the same guy. I will say there's like, every time I talk to people out there dating, it's always like, I get it, you want the spark, you want to be excited, but maybe it can grow into something. Remember what your dating goal is.

[Sarah]

Right.

[Host]

And make sure, generally speaking, you're doing things to meet that goal more often than you're not. It does sound like you're doing the opposite right now. Yeah, you say that this is my goal, but most of your decisions in your daily life right now are not helping you meet that goal.

[Sarah]

Right.

[Host]

And to whatever agree that's accurate. If you think that's fair, then I would just consider that.

[Sarah]

Yeah, no, it's fair. It's fair. It's just, you know, it's just, you know, then you just think about all the other things I have going on that I could prioritize. But to your point, like, I need to maybe prioritize being willing to put this dating goal higher on my list than it is.

[Host]

Yeah. And you can do that for a period of time. Maybe you can say, you know, this summer I'm going to do that. Maybe you need to take a break. Maybe you need to like, deprioritize it for a period of time. Ebbs and flows, you know, it's like it might have been a while where you actually said out loud what your dating goal is and actually thought about how you're moving it. It relates to that goal. Maybe. Maybe this is the first time. So yeah, in the future, it's something you can check in with yourself from time to time. Cool.

[Sarah]

Yeah, thanks.

[Host]

All right. Good luck out there.

[Sarah]

Thanks for the time. I appreciate it.

[Molly]

All right.

[Announcer]

Appreciate you.

[Host]

Have a good one.

[Sarah]

You too.

[Host]

All right, Bye. Bye.

[Sarah]

Bye.

[Host]

Finding a great bottle of wine can sometimes feel impossible. And that's why We Love First Leaf I signed up for First Leaf because I just got tired honestly of lugging bottles of wine from the grocery store grocery store to home. It just became really inconvenient. Also like I was always just buying wine like most of you do, which is just like the color of the label, not knowing much about wine or what I was drinking. That all changed with First Leaf. They send those wines directly right to your door and they give you a great assortment of wines that you usually can't find at grocery stores. Plus they give you information about the wine you're drinking, which is just fun. It's always fun to have a little bit of knowledge of the wine that you're drinking. First Leaf works directly with wineries members get access to award winning wines that may not be available at local stores. First Leaf allows you to manage your delivery schedule so it fits your life. It's just also really convenient. We always have a couple of wine bottles on stock cause of First Leaf and it's always our go to thing to grab, especially if we're going to like a housewarming party or just a friend's dinner. You never want to come empty handed, but usually you're running late. At least we are and instead of having to drive by the grocery store to get a bottle of wine, we usually have one in stock. Thanks. The First Leaf Stop selling for wines that don't quite hit the mark. Head to try firstleaf.com V I A L l to sign up and you'll get 50% off your plus free shipping for an entire year. That's try firstleaf.com T R Y F I R S T l e a f.comv I a l l try firstleaf.comv I a l l if you've ever had an unexpected vet visit, you are not alone. Today's episode is sponsored by the ASPCA Pet Health Insurance Program. The ASPCA Pet Health Insurance Program offers customizable accident and illness plans that can fit your budget, your lifestyle, and even your pet's particular quartz. Because, let's be honest, vet bills can really add up fast. ASPCA Pet Health Insurance has been around for almost 30 years and has covered over 1 million pets. When it comes time to submit a claim, just use their app and receive reimbursement for eligible vet bills directly into your bank account. It's incredibly easy and boy do we love it. We signed up for the ASPCA after two individual experience where Jeff and Steve had to go to the emergency room for eating Something they shouldn't have done. And boy, that was a scary time. And we obviously you want to take care of your dogs, but those vet bills really do add up. But it makes it so much easier and gives you the peace of mind because when that happens, you want to be focused on your pet health and not the bills that are going to come. To Explore coverage, visit aspcapetinsurance.com v I a l l that is aspcapetinsurance. Com v I a l l Again that's ASPCA pet insurance.com v I a l l this is a paid advertisement. Insurance is underwritten by either Independent American Insurance Company or United States Fire Insurance Insurance Company and produced by PTZ Insurance Agency Ltd. The ASPCA is not an insurer and is not engaged in the business of insurance. How's it going? Good.

[Sally]

How are you?

[Host]

Good. What's your name?

[Sally]

My Name's Sally. I'm 32.

[Host]

How can I help Sally?

[Sally]

I want to know how to help my best friend with her future loser brother in law.

[Host]

Okay, so what's, what's going on that it. It's so bad that it's your problem?

[Sally]

It's not my problem, but she's my best friend and she asked me.

[Host]

She is asking for your help?

[Sally]

Yeah. Okay. She did not want to call in herself.

[Host]

Did you suggest that she did?

[Sally]

Yes, I did.

[Host]

So you're like a surrogate basically.

[Sally]

Yeah, we're kind of like one person. So she has been dating her boyfriend for about a year. And the brother in law.

[Host]

Are they engaged?

[Sally]

No, but they're very close to it. They are about to move in together. They. They know it's their person.

[Host]

Okay, so then why don't they get engaged and they move in?

[Sally]

Well, he's still finishing school and I think they will okay. Very soon. They're also not in a rush. It's more about the way it was set up. And he, the Greg. He is actually our co worker at a restaurant.

[Host]

So. And is Greg the boyfriend or Greg the brother in law?

[Sally]

Greg is the brother in law.

[Host]

Okay.

[Sally]

He is the one who set them up.

[Host]

Greg set them up. Greg set them up and we hate Greg.

[Sally]

We liked Greg before. We really liked him.

[Host]

Why don't we like Greg anymore?

[Sally]

He's very arrogant and now he does not like them being together at all. He said it ruined his life and it makes his blood boil that they're together.

[Host]

Why?

[Sally]

We don't know why. We've asked and he just says he hates it and that he can't believe this is happening. I know that he likes keeping things separate, like his work life and his personal life and his friends. He doesn't want anything to mingle.

[Host]

So wait, how? Well, how does work involve this relationship again?

[Sally]

He's our co worker, the brother, and he's been. So he's.

[Host]

You guys all work together? You, your best friend. Yeah, the boyfriend and Greg.

[Sally]

Not the boyfriend.

[Host]

The boyfriend doesn't work. You guys work with Greg?

[Sally]

Yes.

[Host]

This sounds a little almost silly.

[Sally]

Yes, it is very silly. But it also seems like her boyfriend will not say anything to his brother.

[Host]

What's he supposed to say?

[Sally]

Well, it gets to the point where, like, on the boyfriend's birthday, he was going out with his family and he couldn't go out to eat with the girlfriend. They. They excluded her because of the brother because they are, like, worried about what he's going to think.

[Host]

Is he like the manager or something at the restaurant? No, no, he's just another bartender, server. He just works with you guys?

[Sally]

Yep, he just works with us.

[Host]

And so the boyfriend doesn't invite the girlfriend when the brother isn't around?

[Sally]

Yes. They can't be, like, in the same room together. His family's really small. They're from a different country. And so it's just the four of them. The mom, dad, and two brothers. And they will not include her in anything. And, like, he's come to all our family stuff, and so that's like a whole different situation.

[Host]

Well, okay. Well, I mean, I have your answer.

[Sally]

Okay.

[Host]

The brother's not the problem. The boyfriend's the problem.

[Molly]

Okay.

[Host]

Because, like, I don't know, like, she's not marrying or doesn't want to marry the brother. And I can make a bunch of guesses, like, yeah, why? Why? You know, why Greg is annoyed is, you know, Greg is being selfish. I don't know. It's. It's somehow some way. Got it. Weird for Greg that he's working with, you know, his brother's girlfriend, and as they get closer, he just feels, I don't know, like, either. Either it's, like, annoying for him at work where, like, maybe he feels, like, less respected by your friend or something. I don't know. Because, like, I don't have to listen to you. I'm dating your brother. I don't know. Not that he's your boss or anything, but, like, some way, somehow Greg's allowed it to get weird for him, but she's not dating Greg. And she doesn't even work for Greg. She just works with Greg. But for Whatever reason, Greg has some power, he doesn't deserve the person she wants to get engaged to. And the person she's moving in with is, is, is giving Greg that power that he doesn't need to give it. And I don't know if the parent, the parents plan any role, but, like, you know, if he's going to allow Greg to have that much power, then that would, that's a, that's a huge red flag for your friend.

[Sally]

I agree. We've tried to kind of tell him, but like a couple weeks ago he had an opportunity to say like, he was going to move in with her after he graduates. And instead of saying it, he just said like, oh, yeah, I'll definitely need to get roommates.

[Host]

What does that mean?

[Sally]

He said, like, oh, we need to. Once I move out here because we're in the Bay Area, so it's like, you know, expensive. Once I move out here, I'm going to need to get a roommate. And then he's like, yeah, you're going to need roommates for the rest of your life. And instead of saying, yeah, I'm planning on moving in with my girlfriend, he just said, I'm gonna need roommates.

[Host]

Yeah. What does your husband think?

[Sally]

My husband, he's an angel and just thinks that everyone's crazy and that they should both get over it.

[Host]

In fairness to your friend, I don't know, I don't think she's supposed to get over it. I honestly think more than anything she's not paying attention to what are some big red flags and the fact that like, you are, you know, and it sounds like you're just again, being the surrogate here. And she, and I'm guessing she would say the same thing. I'm sure she's probably said my future fiance or my future brother in law. And I think that's a little delusional at this point given how much of a wussy her boyfriend seems to be. Or, or maybe he's just blaming it on the brother. I don't know. But yeah, there's some, like, they're a long way away before getting engaged. And the fact that he's being a little weird about moving in together, which also, like, how old are they? I don't know.

[Sally]

She's 27 and he's 25.

[Host]

Him being only 25, it's not that weird for him not to want to move in with his girlfriend. Is he actually ready to get married?

[Sally]

That's a great question.

[Announcer]

I.

[Sally]

They talk about it and they talk about having kids. They just babysat my 10 month olds.

[Host]

I talked about getting married and having kids when I was 18.

[Sally]

Okay.

[Host]

I didn't get married and have kids until I was 43. I'm just saying there's a big difference between knowing that you want to do it someday and, and being ready for it.

[Sally]

Yeah. I don't know if he's ready. I know she's ready.

[Host]

Yeah. No, that, that makes. I believe that. I think she's so ready, she's projecting her readiness onto him.

[Sally]

Yeah, that could be.

[Host]

And if that's true, it wouldn't surprise me that the Greg feels that a little bit.

[Sally]

Yeah.

[Host]

And there's a possibility that maybe even Greg, as much as he sucks for her and you, that maybe he's not, I don't know, maybe just from brother standpoint, he's just like, it's like, hey, I'm glad you like each other and I'm glad you're really in love. But like, this is moving at a speed that I'm not. You know, again, it's, he's, he only has a right to have an opinion, you know, but it makes sense that as his brother, he has an opinion. That all being said, you know, if she's being excluded by the family, the only one who's going to do something about it is the boyfriend. And there's nothing she can do to Greg or with Greg. And there's no conversation she needs to have with Greg. The only conversation she needs to have is with her boyfriend, which is like, where do we stand? And I think it's a really tough question to ask herself, but a good question is to like, am I projecting what I'm ready for or wanting right now onto this relationship? And, and more than he's ready, I just think she needs to acknowledge that she is dating a man two years younger than him. And listen, my wife's obviously a lot younger than me, but I was more like, I don't know. And she was like, well, you know, listen, you can date me or not, but this is what I'm ready for in my life. And I'm. And, and she was really assertive about that. And it was definitely never a. I definitely wasn't like, do you want to move in with me? And she wasn't like, well, I definitely need roommates. Like, that didn't happen. And I don't think that's something you ignore that he said it the way he did. It was a choice. It was not only a choice, it was probably a statement. It was probably a very Indirect, slightly immature way of communicating to this girlfriend that he's not sure if he's ready to move in with her.

[Sally]

Yeah. Do you think that she should ask him to, like, talk to the brother or should she not even do that?

[Host]

What does she want to talk to him about is the question.

[Sally]

Just like, I think she was hoping that her boyfriend could say, look, we're pretty serious. I want you to, like, just give us a shot at work. He pretends like they're not even together. They, like, keep everything separate and they're, like, friendly at work and everything. But it just. It's awkward because, like, he comes to our cabin with us and, like, he babysits my kids, and I just have to pretend that he's, like, not a part of our life.

[Host]

Wait, wait, what do you mean? Who babysits? Whose kids?

[Sally]

The boyfriend and my best friend. They babysit my kids.

[Sarah]

Okay.

[Sally]

And, yeah, they, like. Yeah, they're very involved with our family.

[Host]

Okay, that's cool. And why is that an issue for. With Greg?

[Sally]

Just because, like, we can't talk about it at work. Like, it feels like we have to, like, hide it because he gets very angry.

[Host]

How so? How does he get angry?

[Sally]

He, like, shuts down and doesn't talk, or he'll be like, can you stop talking about my brother? Like, it's really annoying. And then he, like, goes home and talks to his brother and says, like, can you stop talking? And he's like, have you asked the

[Host]

brother, your friend, your babysitter, and your best friend's boyfriend why his brother is the way he is or why is he acting this way?

[Sally]

Yes.

[Host]

What's the answer?

[Sally]

Yes. He said he always. Their whole family, like, always just, like, tiptoes around everything he does. And, like, he just has a temper, and he's always been this way. And, like, if Greg is in a bad mood, then they all are worried about him, and they all, like, cater to his every need, and it's always been that way. So they just, like, they don't do it a different way.

[Host]

I don't know what your. Your. Your family dynamic looks like in terms of brothers and sisters, but, like, I don't know, like, brothers and sisters are like, you know, they're my brothers and sisters. I don't even. I don't even have to like them. They're still going to be my brothers and sisters, you know? And, like, sometimes when you have a sibling that is just a certain way and you've just accepted who they are, sometimes it's just easier to just Accept it rather than trying to change it because like they're just not going to change. And it's like you kind of choose peace over constant conflict or over being right, you know, back to again. I don't know how productive a conversation with Greg is going to be.

[Molly]

Okay.

[Host]

But you know, because Greg is great and like the information you got back from your friend and her boyfriend is. I don't know, he's been my brother my whole life and I haven't figured out to get through to him, so I'd stopped. Yeah, but what's important is how your friend, her boy, her, you know, feels about their relationship. So she has a right. I don't. I don't know what she's unhappy about or not happy about in the relationship as it relates to those two. But that's the only thing she can't control. The only thing that matters. She doesn't have to ever like Greg. And if Greg's kind of a temperamental guy, like, is it ideal that you guys work with him? No. But he has no power over you. What do you need to talk about with Greg that you can't talk about? That really irks you?

[Sally]

Nothing really. It's just like we all used to be kind of friends, so that's. It just seems like a bummer now that we don't get to like talk to him like a friend.

[Host]

Yeah, totally. But that's Greg's choice, you know. I don't know. You couldn't have been that much of a friend that you can't even been like, why are you being so fucking weird about your brother?

[Sally]

Yeah, he, he likes to cause fights too. So like he's always been an argumentative person.

[Host]

Right. So he's just that guy.

[Sally]

He is that guy.

[Host]

And let's call him Eric the boyfriend. He's confirmed that, you know.

[Sally]

Yeah.

[Host]

To answer how do we deal with him? Is you just don't deal with him. You just have to make sure he can't be the excuse for how Eric moves in the relationship with your friend.

[Sally]

Okay.

[Host]

And she has a right to say I want to feel included by your family. Like, doesn't mean she'd be like, I have to go to every family trip. But like it can't like, like you're not invited because of Greg is like kind of weird. And then like on a one off it's fine. But like, you know, but also like how long have they been together? Only a year.

[Sally]

Yeah, just a year.

[Host]

I think she needs to chill out about marriage. That's great. She's found someone she sees a life with. That's awesome. But, you know, outside of the, like, I've met my person, which is, you know, I guess it's fun to say, but. But, you know, and that's, you know, they're not engaged. It doesn't. And it sounds like he might not be ready to move in. It's also. Okay, I empathize with someone in your friend's position. Knowing that, like, it's never fun to move, like, knowing you need a roommate, not having the idea roommate to move in with, and then also being in a relationship with someone you like, are excited about and you. It's going in the right direction, that can put a lot of unnecessary pressure on the relationship because you're trying to, like, thread that needle. Right? And like, because, you know, you'd much rather move in with your boyfriend than a stranger or, like a casual friend. And, you know, you kind of financially need to. You know what I'm saying? And so you kind of convince yourself you're ready before you actually are, which is like, you know it all. It sometimes works out, but a lot of times it's, like, not great for the relationship. And it just adds unnecessary stress because she doesn't want to. She doesn't even want to consider that maybe they're not ready. And what, like, when I say is a red. Like it's not a red flag. He might not be ready to move in. It's just what he's saying. I don't. I don't know. It just. I. That to me sounds like someone who's not ready and maybe afraid to say that to his girl.

[Sally]

Yeah, I could see that.

[Host]

And I don't think that's Greg's fault. Yeah, I don't think there's the problem solved with Greg because Greg sounds like that guy, you know, And a lot of. A lot of families have that guy. And the way to deal with that person or that guy is to just not deal with him. Let them just kind of be out in their own world and, I don't know, not engage with the person who kind of starts and is argue. Genuinely argumentative. You just kind of avoid that, you know, just. You don't deal with them. That makes sense. Is that helpful?

[Sally]

Yeah, no, it really does. That's kind of. My whole family has been telling him to just suck it up and, like, invite her to stuff. It's really weird that he's not. So I hope. I hope for her that he starts like.

[Host]

And she has a right to say that you, I feel like you're excluding me, but I do feel like there is a more honest conversation they need to have and maybe she needs to have with herself where she can just be like, maybe we're. They've only been dating for a year. He is two years younger than her. And I'm not saying that, you know, but like, you know, in general there's. I see it with my daughter and boys at the playground, like girls mature faster than boys. It's just like, you know, and you know, and you're not describing a highly, you know, emotionally intelligent 25 year old man. So he just might not be ready yet. And, and if she wants to date a man who's two years younger than her, who has a lot of potential, she can. But she, it might require patience. She hasn't accepted that she needs to have.

[Sally]

Yeah, that's great. Yeah, I will let her know. Thank you.

[Host]

All right, well, thanks for the call. Hopefully this is helpful for you and hopefully when she hears this, hopefully it'll be helpful for her.

[Sally]

Yeah, cool. Thank you so much.

[Host]

All right, thanks for the call. I appreciate you. Insurance is at one size fits all. That's why drivers have enjoyed progressives name your price tool for years now with the name your price tool, you tell them what you want to pay and they'll show you options that fit your budget. So whether you're picking out your first policy or just looking for something that works better for you and your family, they make it easy to see your options. Visit progressive.com find a rate that works for you with the name your price tool. Progressive Casualty Insurance company and affiliates Price and coverage match limited by state law. Awkward time to ask this, but. Hey, did you download the trail map? Yeah. No, I don't need to. I. I don't understand. You're trusting your signal out here.

[Sarah]

I'm trusting T mobile.

[Host]

They have the best network.

[Sarah]

And if we end up in bumtots nowhere, well, we've got T satellite for backup.

[Host]

Whoa, I don't trust my carrier that much. We'll just use your phone as a flashlight. With America's best network and T satellite, we're keeping you connected in places you. You never thought possible. And if you switch today, you get free phones for zero down and only 25 bucks a month per line for four lines. Find out more@t mobile.com or visit your local store.

[Announcer]

Best mobile network based on analysis by OOKLA speed test intelligence data 2h 2025 with 24 monthly bill credits and 4 eligible port ins on essentials for well qualified customers with auto pay taxes, fees and 35 connection charge per line credits and imbalance to if you pay off earlier. Cancel contact US Finance Agreement example 299 29.99 Moto Edge 5G required T satellite available with compatible device in most outdoor areas in the US where you can see the sky included with experience beyond $10 a month. Auto renews monthly. Cancel anytime.

[Molly]

Visit t mobile.com Summer is here, which means we all want to look and feel our best. A GLP1 may be right for you. Visit orderlymeds.com to learn more about which GLP1 you could be eligible for. Getting started is fast, easy and happens virtually through telemedicine from licensed professionals. Check out it out for yourself. Go to orderlymeds.com podcast that's orderlymeds.com podcast. Taking care of yourself feels great. Compounded medications are not FDA approved. Eligibility required and determined by a licensed provider. Individual results may vary. See website for details.