E1038 Ask Nick - My BFF Is Pregnant With My Ex

Summary

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The Viall Files – E1038 Ask Nick: "My BFF Is Pregnant With My Ex"

Date: November 24, 2025
Host: Nick Viall
Guests/Household: Natalie Joy, Leah, household members
Episode Theme:
A holiday-tinged "Ask Nick" edition, giving straight-talking, empathetic advice to listeners on complicated love, friendship, and life situations. This episode features confessions and questions about marriage readiness, friendship boundaries, and whether bad kissing is a relationship dealbreaker—all sprinkled with Nick’s signature wit, honest takes, and the group’s candid discussion.

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Episode Overview

This “Ask Nick” is set against a cozy, holiday backdrop, full of personal anecdotes, playful games, and honest listener dilemmas. The episode has three major calls:

1. A woman wondering how to convince her boyfriend of seven years to propose.
2. A fraught friendship dilemma—a woman’s best friend is pregnant by the same man she once hooked up with.
3. Whether a great-on-paper guy who is a “terrible kisser” can (and should) be salvaged.

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1. Holiday Warm-Up: The Household Gets Festive

Timestamps: [02:57]–[09:09]

Holiday Game: "This or That" (Sponsored by Starbucks)

• The group plays a rapid-fire holiday “this or that” game to get into the seasonal spirit.
• Topics debated with playful banter: turkey vs. sides, stuffing vs. green bean casserole, hot vs. iced drinks, gingerbread vs. sugar cookies, real or fake tree, and more.
• Natalie shouts out caramel brulée lattes, Nick stays loyal to peppermint mocha.
• Memorable Moment:
  • Natalie on starting Christmas early:
    [07:46] Natalie: “Definitely launch day... No, as early as possible!”
• Reflection: Family traditions, nostalgia, and small joys set the stage for the heavier calls to come.

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2. Caller #1: "How Do I Convince My Boyfriend to Propose?"

Timestamps: [09:22]–[37:41]
Caller: Kate, 25

Situation Recap

• Kate has been with her boyfriend for 7 years—they started dating at 18.
• She owns a home, is the breadwinner, they live together most of the week.
• She's ready for marriage; he's not. Vague reasons from him: “It’s scary, it’s a big commitment.”
• Kate feels insecure and anxious, “Why isn’t he ready?” She wonders if she’s enabling his lack of motivation.

Key Advice & Insights

Men and Marriage Readiness

• Nick:
  “There’s gotta be a thing… that’s stopping him from being like, this is the woman I want to marry. He lacks that certainty." [12:36]
• Nick highlights generational change: People settle down later, often waiting to “figure out their purpose” before big commitments.

Money, Purpose, Masculinity

• Kate’s BF is unstable career-wise (freelance videography, bartending), while she is secure.
• Nick's Analysis:
  • Men often want to have “their thing” figured out before marrying.
  • Sometimes it’s less about money and more about purpose and masculinity.
  • Unspoken traditional values (“men should provide”) may fuel his hesitation.

Action Steps for Kate

• Encourage him to share his dreams and uncertainties; create a supportive space for his vulnerability.
• Stop guessing his needs—have deeper, goal-oriented conversations.
• Quote:
  “You have to… be willing to maybe hear an answer that might hurt your feelings... It might feel almost like a personal attack, even if he doesn’t mean that... but you really have to talk with him and get him comfortable enough to open up.” [21:04] Nick

On Financial Enabling

• Kate frequently pays his car payments, provides materially.
• Nick’s Firm Advice:
  • “You’re giving him just enough to not want to figure his own shit out... You shouldn’t be paying his car payments.” [33:39]
  • Draws the “feed a man a fish, teach him to fish” analogy—she’s making his stagnation a comfort zone.

Should She Wait?

• If he gives her vague timelines (“two or three years”), Nick says he’s likely just “kicking the can.”
• Quote:
  • “He’s just hoping he’ll feel differently in three years, but he’s not doing anything about it that will make him feel different.” [36:02]

Nick's Bottom Line:

• Recalibrate expectations.
• Stop full financial support unless there’s an equal commitment (i.e., marriage).
• Focus on mutual dreams/goals as individuals and as a couple.
• Don’t “convince” him to propose—help him find purpose, then see if your paths align.

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3. Caller #2: "My Best Friend Is Pregnant With My Almost Baby Daddy"

Timestamps: [40:37]–[51:36]
Caller: Melanie, 24

Situation Recap

• Years ago, Melanie had a “situationship” with a guy—her long-time hookup partner, whom she considered an "almost baby daddy" until a paternity test said otherwise.
• Her best friend (since grade school) is now pregnant by this same guy. Melanie feels weird, hurt, and unsure if the friendship is over or if her feelings are justified.

Key Discussion Points

Sorting Out the Feelings

• Nick:
  “You caring about her getting pregnant with this guy is giving a little... like, you care about a guy you shouldn’t be caring about.” [42:28]
• Melanie is now in a relationship with another man, has two kids, and insists she wants to be happy for her friend, but the situation feels weird and loaded.

Assessing "Friendship Code Violation"

• The “almost baby daddy” was never a serious partner, just a long-standing college hookup.
• Nick emphasizes you don’t get to “call dibs” on casual hookups.
• Unless her best friend acted to spite her, it’s not a friendship-ending betrayal.
• If Melanie is still projecting “weirdness” or resentment, her friend will sense it, risking a drift.

Tools for Moving Forward

• Nick suggests Melanie reach out and affirm the friendship:
  [50:14] Nick: “I want you to know I’m just really happy for you... I value this friendship... and I’m always here for you and I don’t want you to ever feel like you can’t talk to me.”
• “Focus on what you have... This [energy] is a waste.” [51:02] Nick

Key Takeaways

• Emotional closure with flings/situationships is necessary—don’t project leftover feelings into friendship.
• If her gut says her friend was malicious, that’s a separate issue; otherwise, lead with warmth.
• Make space for honesty and mom-to-mom connection as their kids grow up together.

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4. Caller #3: "Is Being a Bad Kisser a Dealbreaker?"

Timestamps: [55:32]–[73:18]
Caller: Lindsay, 29

Situation Recap

• Lindsay’s first date with a guy who is "perfect on paper" (great job, clean apartment, similar values) ends miserably when he turns out to be a “disastrous” kisser.
• The kiss is described as: “Niagara Falls, if you were standing at the bottom with your mouth wide open... no coordination, like he was possessed by some... I’m serious. It was so strange.” [56:21] Lindsay
• She wonders if it’s salvageable or a dealbreaker.

The Bad-Kisser Dilemma

Can Bad Kissing Be Fixed?

• Nick:
  • Asks if she’s ever “coached” someone before.
    “You don’t want to jump to conclusions, but a 33-year-old man who’s this bad potentially isn’t coachable.” [60:21]
  • Suggests some men become “cocky” if they’re attractive and single too long; “Maybe he just needs to be checked.”
  • Sometimes porn or a lack of feedback leads to weird habits.
• Lindsay worries she can't “un-ick” herself; the kiss killed her attraction.

Giving Feedback for Growth

• Nick: Feedback is possible if the guy is open and coachable.
• “Kissing is like dancing… I want you to kiss with me… I feel like we’re not in sync when we kiss.” [64:22] Nick (suggested script)

Red Flags

• Lindsay describes a moment where he was “turned on” by excess saliva, declaring “that’s hot,” which she labels “freaking weird.” [67:12]
• Nick says every kink is valid, but introducing them too early, without consent, is “a bit aggressive” and self-centered.
• What matters: Is he “interested in what you like” and willing to listen, rather than just seeking his own turn-on?
• Nick: “The difference between whether he’s one of the good ones and not is his willingness... if you come in with kindness… if you make it about this is what I like and are you interested in turning me on?” [72:23]

Next Steps

• Nick recommends building rapport, trying a second date, gently addressing the kiss, and gauging how open he is to feedback.
• Lindsay is empowered to decide—if he’s defensive or can’t adapt, “that’s your answer.”

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Notable Quotes & Moments

• Nick on marriage expectations:
  “You’re not sitting around for a feeling, like he is. You’re paying his rent, supporting him… you’re doing just enough where he’s kind of comfortable with his lifestyle, but deep down, he’s not fulfilled.” [36:02]
• On friendship and closure:
  “Focus that energy on being present with your partner instead of, in a weird way, giving more energy to some hookup guy about what he means to you or doesn’t mean to you or whether you should have ‘dibs’.” [51:02]
• On giving feedback about bad kissing:
  “I want you to kiss with me… I feel like we’re not in sync.” [64:22]

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Timestamps for Key Segments

• Holiday Segments & Household Banter: [02:57]–[09:09]
• Caller #1 (Marriage Readiness): [09:22]–[37:41]
• Caller #2 (BFF Pregnant by Ex): [40:37]–[51:36]
• Caller #3 (Bad Kisser): [55:32]–[73:18]

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Episode Tone

• Warm, candid, sometimes blunt but always well-intentioned.
• Insightful takes and humor, even on tough topics.
• Nick leads with empathy, balances realism and optimism.

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For the Uninitiated Listener

This episode dives deep into real relationship messiness—commitment fears, friendship awkwardness, sexual chemistry. Nick’s advice is practical, often tough-love, but deeply human. Listeners can expect honest, actionable steps and permission to set boundaries, have tricky conversations, and focus on their own growth.

Key Takeaways:

• Don't put your life on hold waiting for feelings—seek clarity and shared goals.
• You can’t claim ownership over exes or hookups; friendships require directness and generosity.
• Chemistry matters—and so does mutual respect and communication (yes, even about kissing).
• If it’s hard to talk about, it’s probably a conversation worth having.

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End of Summary

Transcript

[A]

Okay, only 10 more presents to wrap.

[B]

You're almost at the finish line. But first, There, the last one.

[C]

Enjoy a Coca Cola for a pause that refreshes.

[B]

Hey everyone, just in time for Black Friday, we got something a little darker for you. The new Benedict Cumberbatch movie, the Thing with Feathers. Left to raise two young sons after his wife's unexpected death, Dad's life begins to unravel. Grief is messy enough, but when it takes the form of an unhinged and unwanted houseguest crow taunting him from the shadows, things spiral out of control. Critics are calling it memorable and haunting. See the Thing with Feathers starting November 28th. Only in theaters.

[D]

@ this stage of my life, I really focus on my sleep and my quality of sleep and romanticizing the small things in life like going to bed early and my nighttime routine. And that is always going to include a pair of skims pajamas because they are so soft, they feel like butter on your skin. They come in so many different styles and colors and designs and they're not even just good for like sleeping. Like they're good for all day lounging. I love to get ready for bed at around 6 o' clock and then put the baby to be then just like lounge and sit and be cozy and comfortable. You'll find me all season long in my skims. They have so many cute prints for holidays. If you are anyone in my family, stop listening right now because you will be receiving one for Christmas. You can shop my favorite [e-mail] after you place your order, be sure to let them know we sent you select podcast in the survey and be sure to select our show in the drop down menu that follows. And if you're looking for the perfect gift for everyone on your list, the skims holiday shop is now [e-mail] It's.

[B]

That time of year. From family gatherings around a warm fireplace to catching up over your favorite pepper mocha together is the best place to be. This episode is sponsored by Starbucks.

[D]

I have to say, every time I drink a peppermint mocha around the holidays, it always reminds me of when my family after Thanksgiving, the Friday after Thanksgiving, we always go downtown Savannah. We walk the little Riverside Market. There's always a Starbucks there. We like go wait in line. Yeah, you get your hot peppermint mocha. It's cold, you're cozy, you're with family. It's fun. It's one of my favorite traditions.

[B]

Delicioso. It tastes like Christmas.

[D]

It does. It's the most nostalgic feeling ever to like it. Be chilly outside. You have a hot Starbucks holiday drink, and you're like, with your family, there's nothing better.

[B]

Well, we love family time with a warm drink in our hands. Share the season with the peppermint mocha or caramel brulee latte from Starbucks.

[E]

You're crazy.

[B]

What's going on, everybody? Welcome back to another exciting episode of the V Files, Ask Nick Edition. I am your host, Nick. I am joined by the household in this special edition of Ask Nick. Well, it's holiday season. We got Thanksgiving coming up this week, and we thought we'd bring the household in, just talk a little holiday magic, you know, spend time with each other. That's what the holidays are all about in the household. You guys are like family to us, the people listening. And I just wanted to bring in the household. My wife is here and Natalie. I think this is one of your first Ask Nick's, I mean, intros.

[D]

At least I've done, I think a couple before.

[A]

Okay.

[B]

We just want to get you guys into the holiday spirit, you know, like you're about to embark on some family time and hopefully that's going to be enjoyable for you. But like, sometimes, like everything else, it's almost like improv. You have to do a little warm up, you know, when it comes to being with family.

[D]

Yes.

[B]

And.

[D]

And before I let Nick get to his collars, I thought it would be really fun for us to play a little game of this or that sponsored by Starbucks.

[F]

Yeah, I don't know about you guys, but my family, we take games very seriously.

[G]

Yeah, there's always a game going on during the holidays. Me and my family get into it.

[F]

It gets pretty crazy competitive at the Globerman household.

[B]

Well, we're going to play a little game of this or that, like Natalie said. And here's how it's going to work. We're going to go round table, have our this or that, you know, hot or cold, you know, snowy or not snowy. And then for the rest of the household, and if you are listening, you want to join along, you're welcome. But if you agree with the person asking the question, you take a sip of your favorite coffee drink. We're going to be drinking our Starbucks holiday drinks. If you want to play along, press pause right now. Pull into your local Starbucks. Grab your favorite holiday drink. I'm drinking the peppermint mocha. Natalie, also a peppermint mocha.

[D]

No, no, no, no. I'm a caramel brulee. Caramel brulee latte kind of girl.

[G]

Leah And I are also popping off with our caramel braise.

[B]

I guess I'm just a classic man, you know? I'm going with the old Faithful, but super reliable. Okay, are we ready to kick off this or that holiday style sponsored by Starbucks?

[G]

Let's rock and roll.

[D]

Okay, I'm gonna go first. I've got turkey or sides. I'm definitely, definitely going to be meatballs.

[B]

Included in the sides.

[D]

Absolutely not.

[B]

If you know, you know.

[D]

No, no, no. I'm going sides.

[G]

Sides for sure.

[D]

Have you ever had a green bean casserole?

[B]

I'm gonna go turkey.

[E]

Yes.

[G]

Oh, my God.

[C]

You're going turkey.

[B]

If my meatball in the sides, and I'm gonna go sides. But I'm not a stuffing guy.

[E]

You hate turkey.

[D]

Nick doesn't do casseroles or stuffings or stuff like that.

[G]

It's just such a good thing.

[F]

Can't help yourself. I'm gonna drink every time.

[G]

I know. I think it's so good. Okay, wait, wait, wait. So stuffing or green bean casserole?

[D]

Green bean casserole. All day, every day.

[E]

Green bean casserole for sure.

[B]

I'd go green bean casserole.

[F]

I don't.

[B]

I'm not. I don't. I don't stuff a stuffing.

[E]

I love stuffing.

[C]

Stuffing.

[G]

But like the little French fried onions you put on top of a green bean cassero.

[B]

You kidding me?

[D]

So good.

[E]

You kidding me?

[F]

I like when the stuffing gets, like, overdone and it's crispy. Okay. I have a really good one because I literally contemplate with this every single day of my life. Iced or hot?

[B]

Always hot. I'll get hot in 95 degree weather. I am the same way in the holidays.

[D]

Definitely hot.

[F]

I always want hot.

[G]

I'm. I'm iced most of the time, but occasionally it is like a holiday drink. I do like a mocha. An iced mocha. Doesn't feel right in my soul. I have to get like, a steamy, hot mocha.

[D]

Well, peppermint mocha or caramel brulee latte. I'm definitely. You can't. You have to agree with me and drink. You're just forgetting the rules and you're just drinking.

[B]

That's good. I made up the rules anyways. Who cares?

[F]

Were you going to say caramel brulee?

[D]

Of course I'm saying caramel brulee.

[F]

It's a hard choice. They're both really good. In this moment right now, I'm going caramel because that's what I'm drinking and I'm loving it.

[B]

Gingerbread cookies or sugar cookies?

[D]

What is yours?

[B]

Sugar cookies.

[D]

Sugar cookies.

[A]

Sugar cookies.

[D]

Real tree or fake tree? We are fake tree family over here because we start decorating in October, I.

[G]

Think because I never really had a real tree growing up because I was in Florida. Real trees, like, are so exciting to me.

[A]

Ooh.

[G]

Coffee with festive music or coffee with a festive movie?

[B]

Coffee with a festive movie. Music.

[F]

Music.

[B]

Yeah. I want to drink a coffee. I want to, like, you know, start a fire, get some chores done, have my Starbucks drink in hand, you know.

[D]

Have, like, some Frank Sinatra Christmas music in the background, you know?

[A]

Yeah, yeah.

[F]

Or like, driving around, looking at the lights, like you said.

[D]

Driving around.

[B]

Can you imagine, like, waking up in the morning drinking your Starbucks drink and having some jingle bell rock going on in the background?

[G]

Oh, my God.

[D]

Yeah.

[G]

A little Christmas wrapping.

[A]

Okay.

[F]

Eggnog or hot cocoa?

[D]

Definitely hot cocoa.

[B]

Holiday launch day or wait until December?

[D]

Definitely launch day.

[F]

I mean, as early as possible, right?

[D]

No, as early as possible.

[F]

Like, let's get it started. Let's get the holiday season. It's November.

[G]

I do enjoy waiting till December. I'm sorry, you guys.

[B]

When the Starbucks holiday cups come out, you know, it's ready to party the holiday style.

[D]

Well, how about this? New holiday drinks or the classics at Starbucks?

[B]

I kind of like the classics.

[D]

The classics are just like, they hold up.

[B]

Yeah, but the holiday drinks make it, like, again, it just reminds you of the holidays. It mixes it up. You know, you can feel like you're, like, joining in on the fun.

[F]

You know what's fun sometimes, too, is to take a classic and then to put, like, a little holiday spin on it.

[A]

Yeah.

[F]

Or even a classic in a holiday cup.

[B]

How about. What about going out shopping after Thanksgiving or online shopping?

[F]

It depends. Because there is something to like going and getting a coffee, walking around, seeing the lights, being with your family.

[E]

Yeah.

[F]

When I'm online shopping, I'm just like.

[B]

Yeah, you can also have a Starbucks drinking your hand when you're doing that. But I really enjoy going into the store, grabbing my holiday drink.

[F]

I guess it depends if I want an experience or if I actually want to buy things.

[B]

Like, my favorite thing to do with Natalie is going to New York, grabbing coffee and walking around the city.

[G]

It just makes you feel like really, really present and with, like, the person you love.

[F]

And the holidays also always feel nostalgic. Shopping and coffee, no better combo. Literally.

[B]

It's the. It's the best combo in the world. Well, thanks for playing along. Hope you enjoyed this holiday segment. Don't forget to get your Starbucks drinks this holiday season. Now it's time to get to our first caller. How's it going?

[E]

Hi, I'm Kate. I'm 25 years old, and how do I convince my boyfriend that it's time to get marri.

[B]

Okay, why. Why do you have to convince him? Well, I guess let's start. Let's start with why do you feel like you're ready? And despite him not being ready, why do you feel like he should still ask you?

[E]

Yeah. We've been together for seven years.

[B]

Okay.

[E]

So I just feel like time is of the essence now. And so we started dating when we were 18, and now we're 25, and I have a house. He primarily lives with me.

[B]

You own the house?

[E]

Yeah, I own the house.

[B]

What do you mean by he primarily lives with you?

[E]

He stays there, like, five nights a week, and then, like, one or two nights, he goes back to his place. Yeah. So I just feel like, obviously, like, our lives are in sync, like, we're financially stable, and I guess I just don't see the point of continuing to wait until some magical time for him.

[B]

So what conversations are you guys having about your future?

[E]

Yeah, we honestly talk about it a lot. We even did, like, couples counseling earlier this year. And our relationship is really great. I feel like, for the most part, like, we're just very in sync with one another. We're pretty codependent on each other. Obviously, we're very involved in each other's lives, being seven years in. So we've had lots of different conversations, honestly, pretty much weekly about marriage. And he's always reassured me that he wants to get married, he wants to be married to me, he wants to have kids and a family together, but he just doesn't feel like he's ready yet.

[B]

And have you asked him what he needs to get ready?

[E]

You know, Yeah, I have for sure. And he never has, like, a very, like, clear, direct answer. He's always just kind of like, well, you know, I just feel like it's really scary. It's a huge commitment, and I'm like, well, obviously marriage is a big commitment, and. But clearly, like, you're not afraid to be committed to me for seven years and to have our lives, like, completely codependent on one another. So, yeah, that's pretty much the only answer that I get is that it's scary, but someday, like, for sure, we'll be married.

[B]

What if he told you, Jim? Just hypothetical, I'm assuming. Are you guys, like, each other's firsts in A lot of departments. Okay, what if he was just like, hey, like, listen, I just. The idea that you're my only girlfriend or the only person I hooked up with kind of freaks me out. What if he told you that?

[E]

Yeah, I mean, I guess I would understand where he's coming from. But I mean, I feel like if you got it right on the first try, then that's great.

[B]

Yeah, I mean, listen, I just don't. I mean, the thing is, is like I totally get where you're coming from. Right. You years is a long time. You're pretty content with the relationship. I don't mean content in a bad way. I just mean like you're just. Sounds like you're really happy with how things are. And yeah, as a 25 year old dating a guy for seven years, like if I'm in your position, I would. The logical next step would be to, to want this for whatever reason. He, he doesn't yet. Why is he not ready? Right. Yeah, there's gotta be a thing, an actual tangible thing, whether he is aware of it or not. But he probably is that, like that's stopping him from being like, this is the woman I want to marry. Like that we, you know, I love her. Like the only thing I want, that I know I want in my life is her. And he lacks that certainty. I don't know where you're, you know, where you live, where your community is and what you're like the people around you are doing with their lives. But in general, our society is settling down later in life and having dated someone since you were 18 and staying together only to get married is less common than it is common these days. Used to be more common back in the day. So it might just be as simple as that where he's just, he's not sure what he wants to do with his life. You know, where is he in his career?

[E]

So that's kind of another point of contention a little bit. I'm the breadwinner in the relationship, which that's not like anything that I'm upset about by any means. Like I'm totally secure in my career. He's in the interview process right now for like a full time job, but the last couple of years he, he does videography. So it's kind of just like weddings and gigs and social media stuff for other people. And then he bartends at a local restaurant too.

[B]

Okay, so probably safe to say that he's not like living the dream when it comes to his career.

[E]

Yeah, I would say so.

[B]

Is he like career motivated? Is he, does he not care? Is it. Do you, do you sense a frustration from him about like just not being exactly where he wants to be professionally at this stage?

[A]

Yeah.

[E]

And honestly I've thought about that a lot. He hasn't necessarily come out and said like, money is a factor for him, but I do feel like he kind of has those like, traditional values like men should be able to provide in the relationship and stuff like that. And so I feel like maybe that could be a point of contention for him too.

[B]

It might just, it might be less about money and more about him feeling like he doesn't have his purpose yet. And I understand, I'm sure on some level you want to be like, well, I want to be his purpose and his. And listen, like I've said this many times since I've gotten married and have a kid. Like, they are certainly the center of my universe, but I definitely waited until I figured my out, so to speak. And it's a lot easier to feel the way I do, feeling secure about, you know, where I am professionally. Right. And I think that is the case for a lot of men. And you know, there is a level of like, less freedom that comes with marriage. I don't know what your guys plan is in terms of like having kids and things like that, but it wouldn't surprise me if there's a part of him that's just like, I haven't figured myself out yet. I don't know as an individual, as a man, I'm not where I want to be. And then once we get married, it, this life becomes less about what I want and what I want to do and more about us, which is, is right there, there's a truth to that. You want your, you want each other to feel that way to a certain degree. Right?

[E]

Right. Yeah.

[B]

And then you guys start having kids. All of a sudden you're the breadwinner. You're like, well, you be a stay at home dad. And you know, I don't know, maybe he's down for that, maybe he's not. Right. But it could be coming from that place, right. You know, that he hasn't really figured his shit out yet. And I think there's a desire for people to want to do that before they, quote, unquote, settle down. Because there's definitely this idea that once I do that, like you kind of lock into the life that is that you exist. Now that doesn't have to be the case, you know, like you could be a supportive partner and just say, hey, you know, like, you know, I don't know what I would ask him what his dreams are, what does he want to do, how can I support his dreams? I don't know, like how, you know, you guys should be asking each other that. But if that, if that's the case, right, if, if that's what's going on, it might make him feel more secure to choose a life with you if he feels like you will you really have his back and that you are interested in hearing the things he aspires to do and be for himself and that he would have your support. You know, maybe he wanted to go back to school. I don't know, maybe he like, I don't know, I don't know, you know, but you know, part time freelance videography work and bartending is probably, you know, he, I'm guessing hopes to accomplish more than that on an individual basis. Do you have any idea what, what some of his professional dreams and aspirations are?

[E]

Yeah, I think he would love to do just like anything social media for businesses or videography. He's so passionate about that. Yeah, I guess maybe like to be more clear, he's loved like he's done a lot of concert videography and so. And he also loves the idea of travel with that still kind of vague.

[B]

You know, I mean if I'm, you know, I'm not, I'm not critiquing your answer. I'm just like, if that's all you, you know, if, if he's telling me that I'd been like, well, that's not like, if you like, great, you like videography, you like social media, you want to do something in the content, content creation, you know, do you want to start your own business? Do you want to, who do you want to serve? Is it like, you know, you mentioned weddings, Is it small businesses? Like do you want to start your own company? Like the idea of travel, I mean, I guess, sure, you know, depends on, you know, for vacations or for work. Traveling for work. It's pretty old, pretty fast. Yeah, you know, but like I'm not, you know, listen it 25 years old, I mean I was 25, I didn't know what I wanted to do with my life. And that was 20 years ago, you know, and I think a lot of, a lot of young people, Gen Z, so to speak, are, are maturing and growing up later in life, you are, you're ahead of the curb. You know, you got your house, you sound like you have a job that you enjoy, you're making good Money. You feel like that's partly why you're so ready, you know, because you're like, I. My logical next step for me is to get married and have kids. You know, I don't know if you want to have kids, but, you know, but for him, he's just like, I don't know, man. You know? And I think that's probably your biggest hurdle. And so that's not to say you have to wait till he figures it out, because, hell, he might not figure it out for 10 years.

[E]

Oh, gosh.

[B]

But what you need to do is just sit down with him and just, you know, because, like, I, you know, commitment's scary. You know, all those things. You guys have to find some common ground, and it can't just be you pressuring him to propose to you. You have to, you know, you really have to get him to open up about as a couple. Like, what are some things? Like, get them. You have to be willing to maybe hear an answer that might hurt your feelings. Right. Because, like, I am. I'm assuming on some level you just. You don't want to hear any doubt about his desire to propose to you. You know, you've been together for seven years. You. You have a good relationship, so it might be hard to hear. I just wor. If I. You get married, then what am I supposed to do? Blah, blah, blah. You know, I don't know. It might. It might come across a way that it sounds unsexy, certainly not romantic, and it might feel almost like a personal attack, even if he doesn't mean that. But you really have to talk with him and get him comfortable enough to open up about what his real, real feelings are about. Your future.

[E]

Yeah.

[B]

And just be like, hypothetical. Let's play a game. Let's say we got married. You know, let's say we got engaged. What? You know, and just like, you know, you can tell me anything, but, like, what are some. And maybe you open up with something that, like, makes you nervous about the possibility of getting engaged or getting married. You must have some, like, you know, you're a human being. You know, you should have some, like, nervousness doesn't mean you're not ready or you're not going to. But that vulnerability might get him to be vulnerable. Right. And then maybe, you know, it's just like, maybe he can open up, but you have to find out how you can support him. And he needs to hear that, like, it is okay for him to be vulnerable with you and you're willing to listen and you're Willing to say, okay, well, let's figure this out together. I believe in you. I want you to be happy with like what you do for, for your career outside of us, you know, like, I want you to have a fulfilling life. I want both of us to be able to chase our dreams, you know what I'm saying? Like, have conversations like that where you feel like you can operate as a team, you can be his cheerleader, he can be yours. And if you haven't had conversations like that before, he's probably separating his relationship with you and thinking about and feeling a little less than in general or even compared to you because of where you're at with your career and really feeling like he wants to figure his out but having a hard time doing it, maybe doesn't have a lot of guidance. You know, he wouldn't be the first 25 year old person to be like traveling sounds cool. Which is like, you know, we don't know what we want to do. You know, we want to do something that we're passionate about. We want to make some money. It's like we don't know, you know, but he does have to really put himself out there and he has to try and he has to be able to take some swings and have some misses and, and you, you know, very difficult for anyone's psyche. And it's a little easier to do as a single person because you don't feel like you're letting anyone down other than yourself. So you're going to have to. For him to be able to do this while he's in a serious relationship with you, you really have to show that you support him and believe in him and then failure is okay and things like that. Because that's a, probably a big reason what's driving him from feeling as ready as you are.

[E]

Yeah, yeah. And I feel like we've had a lot of conversations like that over the years. And I also kind of wonder if part of it might be the fact that he like his parents were never married and he didn't really experience like an up close, healthy relationship, much less marriage.

[B]

Maybe.

[E]

I mean I certainly, yeah, I grew up with a very healthy example of marriage. My parents are still together.

[B]

I wouldn't assume that. I wouldn't assume that. I mean, it's possible, it's definitely possible. The fact that his parents ever got married isn't like necessarily helping your cause, but it could go both. Like in those scenarios it can go both ways. Right. The, the child who didn't have your traditional upbringing might really Crave that, you know, and want that from themselves and. Or. Or at times, they want exactly what they had, you know, growing up, it's possible that definitely could be playing a role. I also think it's probably just more likely that he. The I'm not ready. Is more centered around. He has other things as an individual to figure out. And if you want to get. And if you want him to prioritize your relationship while simultaneously feel like he can still figure out his out, you have to create a space that makes him feel like that.

[E]

Yeah. So even if I have, like, that safe space for him and we have great conversations about this, you feel like I just kind of need to back off on the subject a little bit, or do you feel like it really.

[B]

Comes down to your approach? Right. Like, it's. If you focus on the engagement and you're like, why haven't you asked me yet? Why aren't we engaged without having any other kind of conversation. Yeah, he might be very resistant. You're definitely like. It's like, this is a. Definitely a threading the needle conversation. But I think this is more about, like, you want to get to a place where I'm asking these questions and you're not guessing that you really understand where your partner's coming from and his point of view and his insecurities and what his goals are and what his dreams are. Now, granted, he might not know exactly what those dreams are either, but, like, you also helping him get there, really, you know, you're guessing, you have an idea, but you don't really know. You know what I'm saying?

[E]

Yeah. Yeah, I do.

[B]

And as someone who wants to be his life partner at this stage in the game, you probably should have a more clear idea of what that is or at least, you know, where he's at. And I just. I can't help but wonder if that's playing a role. I mean, if I think most people, men or women, feel that way, and men especially for all the, you know, and for. For the feeling of. Yeah, a lot of men, you know, their love language is acts of service. They want to feel like they're at least contributing equally, if not more. And they want to enjoy. We all want to enjoy what we do. We all want to, you know, have a sense of, like, you know what? I figured it out, you know, and I. I really. I enjoy waking up and With a sense of purpose for work, and I. I'm proud of the money I make, and I can always aspire for more. But I really. I figured it out rather than like always kind of being, you know, and I remember being in your, you know, boyfriend's shoes, you know, it's just like you're kind of doing fine. Maybe you're making okay money and bartending. You can make really good money. But like, maybe, but you kind of hear what people are doing. And when you meet people who are making good money and like their jobs, there's a sense of like, envy. There's a sense of like. And they like, you know, you really. They seem content with where they are rather than like, I still haven't found my thing, you know, and if he doesn't feel like he's found his thing, it's difficult to feel like you're ready to settle down, so to speak. Because settling down means every, you know, kind of everything else is in place. So you have to create an atmosphere, an environment where getting engaged and getting married isn't. Doesn't exactly mean settling down for the two of you. You know, it's like we commit to each other, but we still have a lot of goals as a young couple, you know, what are your goals? What do you want to do? How can I support you? Here are my goals. This is what, you know, what you two should understand what as individuals, you guys want to feel to accomplish how you guys can support each other as individuals and then what your goals are as a couple and how you guys can support each other as a couple. And that should be a conversation you guys have where you're not guessing.

[E]

Yeah. Yeah. So even if he says something like, I'll be ready to get married in two years or three years or something.

[B]

Like that, that's just him kicking the can. That's him guessing and hoping more realistically if I'm right, you know, that he will have found his thing. He might not even realize that he feels the way he is. Right. He might not like have, you know, again, like, you got to get him to open up. He might not have admitted to himself, like, I'm not where I want to be professionally. You know, he might be somewhat content. You know, it's like, I don't know, I get, make good money, I'm bartend, I'm doing this freelance stuff. Haven't, you know, hasn't really thought about it. But there is something that's stopping him. You know, despite a seven year relationship that is good. There's what's stopping him because you're right. Like, you know, hell, it's been seven years. What's next?

[E]

Yeah, and just without like that Lack of clarity or direction. I feel like I'm just left guessing a lot. And obviously, like, I know he loves me. I know that we're committed to each other and like I said, our relationship is really great otherwise. But I just can't help but feel like this sense of like, insecurity almost of like, why are you still not ready after all these years?

[B]

Yeah. And, you know, don't, don't, don't be like, hey, I sense this insecurity. Why are you insecure? It's. You just try to sit down with your boyfriend and, and be interested in what his passions and dreams are and be motivated to try to support him and be that friend and be that partner who wants to help your partner accomplish his dreams so that you can be proud of him and he can feel proud in himself. And I wouldn't, you know, it's, you know, it's not rocket science like, you know, most people, and especially men, you know, it's like I felt a lot more ready to settle down after I bought my first house. After, like, thing, you know, when I was still dating, you know, when I moved out to LA and I was living with my buddy. But like, I definitely wasn't. Like, it's just hard to really commit, you know, when you haven't figured your shit out. And once you do, then you're. Then all of a sudden it's just like, oh, I want all those other things, you know, And I think that plays a big role and why people want to settle down later in life because I think they're having a harder and harder time finding out what their thing is now. I mean, you know, listen, you know, the job market is. There's a lot of things that make things more difficult for younger generations these days. But also partly is just like, people are also less practical too, you know, if you're, for example, if your boyfriend. I don't know, there's a lot of trades that like, I mean, people can make a ton of money being electricians and plumbers in the trades that are very under. We're lacking. People aren't trained and not skilled. And if, let's say he, I don't know, I'm not saying he might hate that. He might be like, oh my God, I can never picture him doing that. But if you want, if again, I don't know what his passions are. If it's just like having a good reliable job he can be proud of or can be, you know, like, I, you know, I think any electrician, for example, like that's that's a skill set that most people don't know how to do. And you can make good money and people are in need of electricians and like, if you're like, I'm an electrician, I think a lot of people are like, oh, cool, that's a cool ass job. I can't do that. You know, and you make good money. And then maybe he could do freelance on the side, I don't know. But maybe, or maybe his passion is really like, you know, social media and things like that. But he needs to have some kind of plan and purpose, like what is that going to look like? You know, so he has to, he has to hold himself accountable, you know, from being just a dreamer, but.

[E]

Right.

[B]

It's not shocking. I would. My guess is whether that's the only thing. Maybe the parents and never getting married is playing a role. But I don't know. A lot of people, especially men who are excited about getting engaged and married and settling down, if they still feel very unsettled when it comes to like what they want to do for themselves or their career early in life.

[E]

Yeah, a lot of my friends too have said, like, I might have a little bit of like an enabling issue with him and I wonder if like that might have any impact on the situation just as far as like really kind of providing for him financially and maybe like obviously physically for a home and like sometimes I'll pay his car payments and stuff like that.

[B]

Yeah, you shouldn't be paying his car payments.

[E]

Yeah, yeah.

[B]

I mean, listen, if you make it easy for, if you make it just, you know, like, not to get into deeper conversations but like, you know, you heard the feed a man a fish, feed him for a day, teach a man how to fish, feed him for a lifetime. You are giving him just enough to not want to figure his own shit out, you know, and it's a detriment to you and him if you're doing just enough to make him feel comfortable with his lifestyle. And even if he's like a little deep down, not like, you know, where he wants to be, he might not even fully realize that, you know, he's got you to rely on. So you're not married, you don't live together, he doesn't have a commitment to you, you shouldn't be paying his car payments, you shouldn't be paying for anything other than like, you know, the occas dinner and maybe the nice gift. But you're not supporting him and he shouldn't be benefiting from your financial support. Or hard work.

[E]

Yeah, I think I have a hard time with that because I know, like, he struggles more financially and I feel financially secure.

[B]

You know, that's a. His, that's his problem. But like, again, like you, it's, it's not your job to do that. And, and to that point, if he wants that security, then he should, you know, that's, you have that going. You know, he should want to marry you. Like that's what a married couple does. And if he doesn't want to marry you, that's fine. Maybe he's not ready and you don't want to force him if he's not ready, but he, to stop giving him the benefits of what A, of, of a marriage without committing to a marriage.

[E]

Yeah, that's, that's probably true.

[B]

That's. No, I, you know, definitely something. I wouldn't, I wouldn't try. I wouldn't, like, you know, I mean, I would stop doing it right away, but I wouldn't, I would try to do that more subtly rather than, I mean, granted, if he asks, you can just tell him, but I wouldn't use that as a pressure for him to get engaged. More importantly, you want this guy finding his purpose and feeling fulfilled on his own. And yes, if you think he's a little lazy and has a lack, lacks direction, I would stop supporting that.

[E]

Yeah, yeah. No, you might make a great point. I feel like that makes sense.

[B]

Okay, now you have some stuff to work with.

[E]

Yeah, I feel like I have a lot of things to work with.

[A]

I don't know.

[E]

I feel like a relationship is very good, but there are just like some key components that just don't seem to be adding up.

[A]

Right.

[B]

But yeah, it can be very good with some things that you guys need to work on. But it sounds like this whole, you know, the call started with like, how do I convince my boyfriend of seven years to propose? And it's like, right now, I don't think that should be your primary objective. Your primary objective should be recalibrating expectations. Stop supporting him financially and most importantly, having an understanding about how you guys can support each other as individuals and the dreams that you have and what are your goals as a couple. And make him feel like he has value and that you believe in him, but you're also challenge him that he has to get a shit. You know, that he's going to have to make this happen, but you're not sitting around for a feeling. Like, you know, like he is sitting around for a feeling. You're paying his rent you know, you're supporting him. You're doing just enough where he's kind of comfortable with his lifestyle, but deep down, he's not feeling fulfilled. And that's why it's just like, I don't know, I'll be ready in three years. Like, no, he's just hoping he'll feel differently in three years, but he's not doing anything about it. That will make him feel different.

[E]

Yeah. And he definitely has said in the past, too, that he is, like, he's used those words, that he's waiting for a feeling, and he's waiting to feel like some sort of, I don't know, magical moment that he's ready, which.

[B]

I don't know. It's never gonna happen. It's not gonna. It's not gonna. Yeah, yeah. He's wearing. You're waiting for a miracle. Well, good luck. Hopefully this is helpful.

[E]

Thank you. Yeah, thank you so much. I definitely have things to work on, so I'll be doing that and.

[B]

All right, well, keep us posted how it's going.

[E]

Okay, Sounds good. Thank you.

[B]

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[C]

It's good. How are you?

[B]

Good. What's your name?

[C]

Melanie. I'm 24.

[B]

And how can I help?

[C]

Melanie, my best friend is pregnant with my almost baby daddy and I am baffled.

[B]

What do you mean by almost baby daddy?

[C]

So I got pregnant in my ho phase and so it was between one of two guys and it wasn't him. So almost.

[E]

Okay.

[B]

You thought it might be. You didn't know for sure.

[C]

Okay, yeah, yeah. I got a paternity test.

[B]

And then your now best friend has since hooked up with this guy and is now pregnant with him?

[C]

Yes.

[B]

Okay, is this like, are you just having a hard time processing it? Are you feeling betrayed by your friend or like, what, what can I help you with other than like you telling us a couple crazy story and us being like, oh my God, she doesn't.

[C]

Fully understand that, like I'm upset about it and I don't know if I have a right to be upset about it. Like, is this something that, like, is this a friendship ending thing? Because, like, it's so awkward, like, even being around her anymore. So, like, I was just hoping to get some advice on, like, how I move forward and just, like, the awkwardness.

[B]

What's your current relationship status like, personally?

[C]

Like, I. I have a house, I have a family. I have two kids.

[B]

You have two kids? Okay.

[C]

Yeah. So I've had a second one since.

[B]

You have a partner?

[E]

Yes.

[B]

Okay. Are you guys married?

[C]

No.

[B]

Okay. What is. Are you happy?

[C]

Yeah, for the most part. All right, we have our issues, but.

[B]

I mean, everyone does. But you feel like you're work for. Feel like you're working on your issues?

[C]

Trying.

[E]

Okay.

[B]

I mean, like, yeah. So I. Let's just start with, do you have a right to be upset? I mean, you caring about her getting pregnant with this guy is giving a little. Like, you care about a guy that you shouldn't be caring about.

[C]

Yeah.

[B]

And to be clear, did you, like, really date this guy, or is he just some guy you're kind of hanging out with? He was, like a hookup buddy for a period of time.

[C]

Yeah. So a little backstory. Him and I were hanging out all summer. We never, like, put an official title to it, but we were basically doing everything boyfriend girlfriends do without the title. And this girl also, like, hung out with us. Like, she would third wheel with us on dates every once in a while. That's something like her and I used to do. So, like, she was, like, fully a part of our situationship. And then also I would talk to her about everything. And then him and I continued hooking up for, like, multiple years after this, like, summer fling. So we hooked up for probably, like three years. And like, the most recent hookup was in, like, within a year of her getting pregnant with this guy. Sorry, I can slow down if you want me to. Like, how long you've been.

[B]

How long you been together with your current partner?

[C]

A little over a year and a half.

[B]

Okay, so. So who is the baby daddy of your firstborn?

[C]

He's not in the picture at all. He wants absolutely nothing to do with.

[B]

Okay, gotcha. So you're not with that guy. So you didn't cheat on your current partner with this guy, right?

[E]

No.

[C]

No.

[B]

Okay, so you were hooking up with two guys, one being this guy that your friend now got impregnated by, and then the oldest's father. You weren't sure who the father was going. It was. But you took a paternity test and realized it was this other man who has peaced out in your life, the guy that you thought it also might be. You kept hooking up with him after you had your firstborn.

[E]

Yes.

[B]

Okay. Did she know that?

[C]

Oh, yeah. I mean, she fully was. Like, I talked to her about everything. Like, she's been my best friend for, like, since third grade.

[B]

What? Ha. Why did that end? And then how did you meet your current partner?

[C]

It kind of ended because of my current partner. We would hook up unless one of us was. He was never in a relationship. We would just hook up unless one of us was me, unless I was talking or dating somebody else. So that's how it stopped, is I started dating somebody else.

[B]

All right. I don't think you have much of a right to be upset here.

[C]

I mean, I'm happy for her, and I want the best for her. It is just. It's so awkward to me that.

[B]

It's only awkward because you are choosing to make it awkward. Right? I mean, listen, you have two kids, you have a partner, you're living with each other, you're playing house, you're not married yet. But, like, everything about your lifestyle is a family unit, and you have. You have a, you know, a beautiful thing going. I think that's where your priorities need to lie. You had a hookup buddy that, you know, sounds like if. My guess is you kind of had some feelings for or, you know, it dragged out. You felt a certain way, but, like, I don't know, it never, never happened. And then you met your partner, and I'm assuming and hoping that you. You were busy being a mom and busy in that relationship. And I don't know, your friend was single and she knew this guy. There was a comfort level there. I mean, like, it's not a crime that they, like, had a night where they went out and hooked up. And I'm sure he pursued her just as much as she pursued him and got pregnant. I mean, like. But, like, you don't get to call dibs on this guy, you know? And I understand it. You can feel a certain way about it, but, yeah, it's not like, it's just weird for. For you to hold some. Like, she stabbed me in the back. And I'm not saying you are, but, like, whatever weirdness you're feeling, there's a feeling you clearly have some kind of, like, did she betray me? Like, was she supposed to do that? Like, is it kind of fucked up that she did that? And, like, you know, again, I don't know. Her situation. Maybe, you know, maybe she did it to spite, you know, like, if you think, unless you think this girl has some secret jealousy for you and is more of your frenemy than your friend, and you really think that's what she's all about, and she hooked up with him because she wanted to have what she suspected you wanted to make her feel, then, yeah, I mean, if that's who you think this friend is, then you should have a problem with it. But if that's not what this is, if this aside, she's a good friend with a good heart who wants love and, and wants a connection. And like you and everyone else out there who's had, you know, a difficult time with dating and, you know, everyone's just kind of very slapper daters that she ended up hooking up with this after you were in a relationship with two children playing house, you know, that she, like, you know, met up with a familiar guy and things went down and she got pregnant. I, I, yeah, I think you should just be happy for her.

[C]

And I am happy for her. Like, I just was at her baby shower and like, it's just everything changed. Like, I found out she was pregnant on Facebook and I don't know, like, when I was, got pregnant with both of my kids, she was my.

[B]

Yeah, but like, you, you've acknowledged that you, you think it's kind of weird, and she might think it's kind of weird. So, like, if you really value this friendship, you know, she's the one who's pregnant right now. She's in a vulnerable, probably state of mind. I don't know. But like, if, if you're comfortable with it and you value this friendship and you want the weirdness to go away, then you should call her up or take her off her coffee and just say, you know what? I want you to know I'm just really happy for you. And like, and I know him and I have a past, but, like, I'm happy with my, like, like, I just want to know that, like, I value this friendship. I wouldn't even, you know, but like, I'm really happy for you and I'm always here for you and I don't want you to ever feel like you can't talk to me, you know, and make it safe for her to open up. You know, she might be feeling weird. She might have been worried about what you were going to say or feel about this. So let her know you don't care, you know, but like, she's, you clearly weren't sure and aren't sure if you care. She's not, you know, so she wouldn't be wrong for worrying about you caring and feeling uncomfortable with calling you up and being the first person she told. Like, you know, it's like, you want to be the first person, like you told her, but, like, she was, like, kind of hooked up with the guy that she was hooking up with. And, you know, there's definitely some weirdness here. And again, like, you know, this person, hopefully, certainly I don't know who this person is. If your gut tells you that she had alternative motives and that she's a little shady, then, you know, that's a different story. But, you know, this wasn't like your ex boyfriend, certainly not your ex husband. It was your hookup buddy, you know, and you moved on with your life, and she hooked up with a familiar friend.

[C]

Yeah, I think just having that conversation of, like, I hope you know, you can still, like, come to me is gonna be important, just. Cause I do want her to know that. It's just.

[B]

I'm so excited you're having a child, and we have both young kids. I. I'm really excited to spend time with you and have our kids play, and I'm here for you. And being a mom is hard. And, like, if I can ever, like, whatever. Whatever I can help with, like, advice or just, like, be there for each other, you know?

[C]

Yeah.

[B]

But if you are at. If you're feeling like it's a little weird, then you're projecting that weirdness and she can pick up on it, and then she senses it, and she's wondering if you're mad at her, and then you both kind of, like, get weird around each other, and you both kind of stop talking, and it's just not worth it over a guy who's, like, not your guy. And the only thing that would stop you if you think she's a bad person who. You think she's kind of shady and deliberately did this, and I'm not sensing that.

[C]

And from you, no, she's. She's definitely not. Yeah, Somebody doing it deliberately. That helps a lot.

[B]

All right, good luck, hopefully. Yeah, let me know. Let me know how it goes. But focus on what you have. You're. Don't. You're. This is a waste of your energy. You know, you asked you how your relationship's going, you're like, okay, you know, listen, focus that energy on. On being present with your partner instead of kind of, in a weird way, giving more energy to some hookup guy about what he means to you or doesn't mean to you or whether you should have dibs. Focus that on, on your family.

[D]

Yeah.

[C]

All right, that makes sense.

[B]

Okay, take care.

[C]

All right, thanks.

[B]

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[D]

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[B]

How's it going?

[A]

Hey, I'm Lindsay. I am 29 years old and I'm curious to know if being a bad kisser is a deal Breaker.

[B]

Who's the bad kisser, you or him?

[A]

Well, I must. I'm coming on here because it's not me. It's another guy that I met. And let me tell you, it was quite possibly the worst experience of my life. The issue at hand, though, is that on paper, he's perfect. He's perfect.

[B]

Well, other than on paper. What like. Like, paper doesn't mean much. But what about in life?

[A]

Okay. Oh, beautiful. Like, he's got a great job. I did go to his apartment. Like, everything was good up until our lips touched, basically.

[B]

How? Like, describe the kiss.

[A]

Okay. Have you, like Niagara Falls, if you were standing at the bottom with your mouth wide open.

[B]

He was in this picture, so it was too aggressive.

[A]

It was no coordination. It was like he was possessed by some. I'm serious. It was so strange. And I've had my fair share of smooches. I've. I've had bad kissers. I'm sure I haven't been great in the past too, but, like, this was exceptional.

[B]

Like, how long could you go about.

[A]

Kissing this guy right before I get to a point where I can tell.

[B]

Him, yeah, like, how long? Like, how. How long could you put up with it?

[A]

That's the thing. Like, no, like, I can't. Like, I would have to not kiss him again.

[E]

That's.

[A]

It. Was that bad?

[B]

What is. Tell me, about how many dates have you been on?

[A]

We've only seen each other once because I haven't really made up my mind yet about if I want to go. Because he's such a great guy.

[B]

What makes him great?

[A]

We have, like, a lot of the same outlooks on life. We live really close to each other. I have three older sisters, and that's like, the most important part of me. And he also has three older sisters that he's extremely close with. We immediately bonded on that. Not that that's huge, but he's well educated, which I appreciate. He's just a really nice guy. Really fun, takes care of himself. His apartment was nice. His apartment was clean. He had, like an adult male apartment. I was impressed. That's why we got to a point of sharing a kiss.

[B]

How long? Like, so you've only had one date?

[A]

Yeah.

[B]

How many conversations leading up to this date did you guys have?

[A]

Like, a. Quite a few. Quite a few. Nothing over the phone, though.

[B]

How old is it?

[A]

He's 33. Yeah. Why are you 33 and you can't kiss and you're good looking? There's no.

[B]

He's single now. He's single he had a, what was his, how long was his last relationship?

[A]

He said three years ago.

[B]

He's been.

[A]

But he, but while he's, but while he said that, he was like, it. I'm not, I haven't been in many relationships. The last one was probably about three years ago, so it didn't really sound like, oh, like we broke up three years ago. You know what I mean?

[B]

Have you ever had to give a guy like a kissing note before?

[A]

Yeah, and like that's fine. Like, I think that's okay to do if you're respectful about it.

[B]

Yeah, but you think he just needs.

[A]

To tell someone that they actually like completely turn into a different person and they need to be, they need to go to school.

[B]

Well, I don't think you say it like that. Right. I think that's something you say after you're married. You'd be like, the truth is you. I mean, it was terrible. Like we were.

[A]

I know, I'm just a very upfront person.

[E]

Sure.

[B]

But you can be upfront at the right time and place. Not to your detriment, you know, listen, if you want to be, if you're done with this guy, you want to give him some direct feedback and you don't want to be nuanced for the, you know, because you don't have time, then go ahead and be direct, you know. But if you're seriously interested in this guy, knowing that, like, listen, on paper doesn't mean much, you've only had one date.

[A]

But like, Kate, how about if a girl like back in your day told you that you were just the worst.

[B]

Kisser, I would be very interested in learning why. I mean, like, I've told this story before. I mean, you know, when I was in high school, I received some feedback from the girl I was quote, unquote dating, you know? You know, you're in high school, you're kind of messing around and rounding bases and, you know, it's very juvenile and you don't know what you're doing. And yeah, I received some feedback from her friend that I, that really, honestly was very helpful. Yeah, I've always, I've always been coachable. You know, my sports background, that's great.

[A]

We love that about you.

[B]

Listen, like it's a, you know, listen, I don't want, you don't want to jump to too many conclusions, but a 33 year old man who's this bad potentially isn't coachable, you know, and if he's not, you know, or not open to feedback, I'd be curious of how sensitive he is. Like, I know some really great people who aren't very coachable, you know, and they just shut down and they get in their feels. You, you know, you're describing this guy who has a lot going for him. Right? You know, over six foot, you know. Right. Yeah.

[E]

Yes. Yeah.

[A]

Yeah.

[B]

He's. He's a 1 percenter. So like, like, he is he.

[A]

And he's extremely handsome. I really need that.

[B]

So, like, so that's the thing. So he clearly gets attention from women. You're not the first date. It's not like. So why isn't. Why isn't. Why is he like this? You know?

[A]

Yeah, no, well, that's. That's why I'm here. I'm curious to know if you have any thoughts. Just like, you know, because I've spoken to so many people. Not so many. My close friends and my sister, my family. And they're like, well, you know, like, that's something everyone says. That's something you can teach. That's something you can get over. Like, that's not a big deal. I understand that. Like, I know, but how far do you have to go before you can get to that point? And because we've only met each other once, we've already kissed. It could have escalated further. I stopped it from escalating further. I didn't want it to because the kiss was that bad. I'm like, done.

[B]

Maybe he's just watching, like, weird porn or something.

[E]

I don't know.

[B]

Maybe he's been single for too long.

[D]

That's what.

[A]

That's what someone said to me. And I. It could be because I have never experienced.

[B]

It's possible. Listen, like, honestly, I think porn's a problem these days. And I think single men, you know, it's kind of probably what they do.

[A]

Yeah. I don't know. It's very strange to me.

[B]

Yeah, listen, it's a delicate way because, like, I think all guys should be open to feedback, but certainly how you give it, it. It matters.

[A]

And the thing is, like, I do. Everything was great up until that point. Like, I was excited. I was pumped. I'm like, okay. And I was excited to go on, to go on the date, to meet him. And I was excited, everything about it. But, you know, so disappointing for sure. But trying to figure out if I can get through it, get. Get over that. And I just don't know.

[B]

What if. What if, like, I mean, listen, I. I would. If you're clearly, you're still interested in this guy. So I would just keep Talking with him.

[A]

Okay.

[B]

You can punt a date for the time being in the short run, you know, a week or so. Keep talking to him. Try to learn more. Learn about his past dating history. Just with invested. Not like you're interrogating him, but like just a genuine interest in learning more about the guy who knows the answer. Might, like, it might work itself out before you get to the awkward stage. He might flake on you. You might get the ick. Some other reason. But like, let's just assume that, like, everything will maintain and you'll continue to get to know him and you will still be like, yeah, no, pretty good guy. Like, you know, really, really enjoy this, the conversation. So you, you hang out again, you have a nice night, you're in a position to make out again. And I think you're just kind of like, hey, can we talk about our kiss? Basically, it's I. I think it's like, correct me if I'm wrong, but it's like he wasn't. You know, kissing is like dancing. You know, it's like, I guess the Guy should lead 9010. But it's a dance. You know, when you're making out, you know, there's a bit of like, rhythm. Rhythm. Right. And everyone kisses different. Right. And I just feel like as guys, you know, there's a you, you, he, a guy. He's not paying attention to you in that moment. He's kissing your face.

[E]

Yes.

[B]

He's just going in and doing his thing and expecting you to respond. So in the gentlest way, you could just be like, I want you to kiss with me. You know, I want like. I feel like we're not in sync when we kiss. Maybe you make it a thing. It's just like, hey, I was.

[A]

That's good.

[B]

I was a little surprised by our kiss because I didn't feel like we were in sync. You know, I didn't feel like we were dancing. You know, I like a more gentler approach. Maybe we'll get like real hot and heavy someday and we can go balls of the walls. But like, for a makeout, I like a little dance. I like a little like, you know.

[A]

I wanna romance, passion.

[B]

Well, you know, I wouldn't like, not sit. Don't say no. I know, but like, I think I'm.

[A]

Not saying that to him.

[B]

Yeah, right. It's just more like, I think when I'm just saying on a second. On a second day, when a woman's like, I just want to be swept off my. It's just a little like I know. It's like. No, I get it. You know, I'm not. Like, you should want that. It just comes across a little.

[E]

Yeah, yeah.

[A]

No, no, that's not something I would say. Hell no.

[B]

But it's more about. I don't know, it's a flirtation. Like, he should want to flirt with you when he's making out with you. You.

[A]

Yeah.

[B]

If that makes sense.

[A]

No, I 100 agree. It's the. To everything else.

[E]

Right.

[B]

You know, I want to be keys. I want to be this. And you make it a. Like, we, like, forget about claiming he's a bad kisser or why, but, like, you're just not like the other he's dated kind of thing, and you're a new. Like, you know, I presented that way, you know.

[E]

Right.

[B]

But like, and then the big question is. Is, like, is he coachable? Is he willing to say, okay, cool. Like, show me. Show me what you like. I care about what you like. I. I'm down for anything. You tell me what you. You want me to spit in your mouth? I'll spit your mouth. You want me to give you a. You know, like, what do you like? You know, like, the question is, is he open to hearing you out and is he interested in hearing what you like and how you like to be, you know, won over and how you like to be romanced and. And what you like in the bedroom, so to speak? He, you know, he should be interested in. I think any decent guy, you know, should.

[A]

And that's.

[B]

Should be.

[A]

That's also why it was confusing because in our conversations, overall, I got high emotional intelligence vibes. I just, you know, so to me, that would.

[B]

Ideally, maybe this is maybe just off his game. You know, Maybe he just got a little turned on, got a little aggressive, and just, like, forgot how to make out with women. I don't know.

[A]

I guess. Yeah, maybe. I don't know. It was a lot.

[B]

It's a little weird that he, you know, never been told. Yeah. I don't know.

[A]

You know, Very interesting.

[E]

Yeah.

[A]

So. Yeah.

[B]

But if it's so bad, it's not an easy conversation, you know, but.

[A]

Well, like, it was so bad. Like, he was turned on by, like, there was, like, lady and the Tramp saliva between us. It was that gross. And he was turned on by it. Like, he was like, oh, that's hot. And I was like.

[D]

I pulled back.

[E]

Back.

[B]

Okay, well, that's a. That's. Yeah, that's a problem.

[E]

Yes.

[A]

Yes. But then he'd, like, turn back into his own. That's what I'm saying. It was like he was possessed, but. Yeah. Strange. Anyway. Yeah.

[E]

Major.

[B]

That's hot.

[A]

Yeah.

[B]

He might be watching some porn.

[A]

I think so. Maybe that could be because it's freaking weird either way.

[B]

Like, and he. He is allowed to have his kinks, and he's allowed to, like, a little extra saliva, but it's a time and a place, and you're not there yet, you know?

[F]

Yeah.

[A]

No, like, maybe later when it's better.

[B]

Yeah. Yeah. I would take that approach. I would just.

[A]

Yeah.

[B]

Can we talk about our kiss? And you'd be like, yeah, sure. What do you mean? You know, And. Yeah, you just. You have to try to avoid. You're a bad kisser. And it's more about. This is what I'm down for. I was a little caught off guard. It was. It was a. You know, the harshest. You want to be. Is to say, I didn't feel like you were kissing me. I kind of felt like you were just kissing me. How you kiss, as opposed to, like, connecting with me. And that. That moment, you know, that. That's definitely direct, you know, in a. In a relationship, in this stage of the game.

[A]

For sure it is. Yeah.

[E]

But he's. He's a.

[A]

He's an adult.

[E]

He can take it.

[A]

He should be able to.

[B]

Yeah.

[A]

And, like. And we'll see. And I guess it's like, we'll see what he does with it.

[B]

But I would.

[A]

Yeah, you're right.

[B]

I would spend the next approach. I would spend the next week building some rapport with him.

[E]

Sure.

[B]

And trying to emotionally move this relationship forward.

[E]

Work.

[A]

Yeah.

[B]

So that.

[A]

And see if that can improve it as well.

[B]

Yeah.

[A]

Make me feel better. Yeah.

[B]

Or just, like, you know, it might. You might figure out again, you might not be into it. You might. You know, I don't know. Maybe it might solve itself. And, you know, it might also make him feel more comfortable with you when you have this question that he's right. Spent more time with you. And he's like, you know, you. You want him to be like, I really like this girl. She's great. You know, she. You know, whatever makes me feel this. Feel that.

[A]

Like, he's still texting me and stuff, so. And I respond. It's just. I mean, I. We both have the very great excuse of being busy, so that's kind of like, I'm busy recording a podcast right now. I can't hang out.

[B]

There you go. And so you just stopped talking. No.

[A]

Or what, like, kissing.

[B]

Did you, like, leave right after?

[A]

So I like stopped. I was like, I don't want to do anything else. I was like, I'm good. I was like, you know, not a first date, whatever, like use that kind of thing. And he was respectful of that. He did try to kiss me again. And like, I did. I like approved of the kiss or sorry I went in for it because I thought maybe it would be better. It wasn't. And then I was like, I gotta go. And very quickly I left. Yeah, but it, but I didn't leave in a obvious way that it was because of the kiss. This, you know, I just happen to make my way to the door sort of.

[B]

The fact that he said that's hot afterwards is red flag.

[E]

It's crazy.

[B]

He's got a kink, you know.

[E]

Yeah.

[A]

And that's fine. I'm not kink shaming. That's okay. It's just this was the first time we kissed. Like.

[B]

Well, it's a bit back a little. It's a bit presumptuous of him if, if. Yeah, you're right. If it, if it's a kink, great. But he shouldn't be so confident that.

[E]

He can put that kink on me right away.

[B]

Yeah. To like introduce a kink without honestly not to say your consent is a little aggressive, I suppose. But like in a weird to presume my approval to presume that you're gonna be down and it's less. It. It's also showing that like when it comes to the bedroom, he's more concerned about what turns him on rather than what turns you on on. And there should be a little bit of like that's that, you know.

[A]

No, that's not how things work.

[B]

Yeah. So.

[A]

Yeah. And I did get those vibes as well because of this. I was like, maybe this also will show me. Or this translates into maybe how he.

[B]

But I do think men, you know, we all need to get checked from time to time. If he hasn't had a girlfriend in a few years, he just might have gotten a little. He just needs to be checked. Well, not only excited, but just like a little. A good looking six foot guy gets a little cocky and a little. And there's a lot of people out there, you know, women he's dating who are. Who don't feel comfortable checking him or don't want to waste their time bothering. And I think he might have a false sense of confidence about, you know, that everyone's into him. So.

[E]

Yeah.

[B]

The difference between whether he's one of the good ones and not is will be his willingness. If you. If you. If you come in with, like, kindness and you're not trying to, like, minimize, belittle him without patronizing him and make it more of like, this is what I like and are you interested in. In turning me on? And he's very. Any. And he sounds very interested in turning you on and doing the things that you like, then that. That's a huge green flag or. Or a huge red flag, right?

[A]

Yeah. Totally. What he does with the information. Totally. Will tell.

[E]

Yeah, I guess. Yeah, you're right.

[B]

All right.

[A]

I mean, there's lots else, but that's enough for today.

[B]

Okay. All right.

[A]

Thank you so much, Nick.

[B]

My pleasure. Take care. Let me know how it goes. Definitely wanna. Yeah.

[A]

I'll keep you guys posted if anything changes.

[B]

Sounds good.

[A]

Okay. You have a good one.

[B]

You too. Take care. Bye.

[D]

Bye.