Is the Pen Pal Dating Trend Back?

Summary

U Up? - Is the Pen Pal Dating Trend Back?

Date: October 17, 2025
Hosts: Jordana Abraham & Jared Freid

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Episode Overview

In this lively Friday Feels episode, Jordana and Jared dissect the resurgence of the "pen pal" dating trend—where people end up texting endlessly without making concrete plans to meet. Spurred by a viral TikTok from Bethenny Frankel, the hosts explore why this behavior is common, who benefits from it, and share their personal takes and advice for listeners stuck in digital limbo. The episode also features their popular "Petty or Prudent" segment on post-breakup etiquette and a discussion about navigating friendships with significant age gaps.

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Key Discussion Points & Insights

1. The 'Pen Pal' Dating Dilemma

Starts ~01:18

• Bethenny Frankel's Viral Question ([04:10])
  Bethenny Frankel shares her confusion about men who only want to text rather than make real-life plans:

  "So you'll go out with someone one time, like each other... Sometimes it's so far between the first plan and the next plan that you forgot about them. One person said to me, 'Oh, what are your plans in November?' I'm like, I'll be dead in November. What are you talking about?"
  (Bethenny Frankel, 04:10)

• Jared’s Perspective on Bethenny and the Trend
  Jared expresses frustration at the ongoing confusion around the pen pal problem, especially from accomplished women:

  "We've answered this for seven years... These men are not stupid. They know what they're doing."
  (Jared Freid, 01:31)
  He reflects on how TikTok both helps and hinders public figures like Bethenny, sparking endless conversations on repeat topics.

2. Why Is 'Pen Pal Season' Back?

Starts ~07:04

• Seasonal Factors
  Jared explains that fall brings fewer excuses for not meeting up, causing more people to get stuck in texting limbo:

  "You know why it's pen pal season? Because it's fall. There's less excuses [not to meet]."
  (Jared Freid, 07:05)

• Gendered Socialization and Scarcity Mindset
  Jared reflects on male behavior rooted in societal expectations:

  "When you get someone who will talk to you—a woman that will talk to you—you hold on to her like she's an acorn that you might need when it starts snowing."
  (Jared Freid, 08:08)

• False Intimacy & Misaligned Expectations
  Jordana describes the disconnect:

  "Men will text you like you're your boyfriend and you've been on one date. And there is this false sense of intimacy..."
  (Jordana Abraham, 08:38)

3. Spectrum of Reasons for Pen Pal Behavior

Starts ~09:51

• Why Do Some Men Pen Pal?

  • They like having options and the ego boost of an interested person
  • They’re lonely and want attention
  • They’re transitioning out of another relationship and keeping backups
  • They have no real intention to meet, just enjoy the flirt
  • Sometimes, they're genuinely busy, but this is rare

  "There's a number of reasons a guy pen pals. One: they really like getting a text from someone. They're lonely and you're just someone."
  (Jared Freid, 09:51)

• Key Quote:

  "Men love vague options. So they text and text and text all..."
  (Jared Freid, 10:42)

4. How to Respond to Pen Pal Behavior

Starts ~12:46

• Jordana Asks for Advice:
  What should you do if a guy is texting but the next date is vague or weeks away?

  "How do you recommend I deal with you [if you're pen palling]?"
  (Jordana Abraham, 12:46)

• Jared’s Advice:

  • Be clear and prompt: "Hey, I'm game for next week. Just make a plan and I'm in."
  • If met with vagueness, respond with light-hearted acknowledgment, then pivot: "Well, when you're ready, shoot me a text for a plan and we'll see if I'm free."
  • If you're uninterested, simply stop engaging: "I just wouldn't even answer." (Jared Freid, 15:17)

• Honesty and Boundaries:
  Jordana emphasizes her position:

  "I relate much more to [Bethenny] where I'm like, I don't really care about you visiting your niece this weekend. Like, I don't really know you."
  (Jordana Abraham, 16:39)

  Jared counters that he doesn't mind ongoing texts, showing how perspectives can differ even among daters.

5. Mixed Signals and ‘Relationship’ Definitions

Starts ~18:10

• When Does Pen Pal Behavior Become a Problem?
  The hosts discuss how confusing it can be when texting suggests connection, but real momentum isn't there:

  "I do think it's like... tough when you're like, I actually do want to see this person for a second date. I want to keep talking to them, but I don't want to keep talking to them in a way that feels like it's going nowhere."
  (Jordana Abraham, 18:10)

• Key Insight:
  The difference between someone looking for real progression and someone just enjoying casual attention is often the root of pen pal frustration.

6. Petty or Prudent: The Post-Breakup Survivor Pool

Starts ~27:10

• Listener Email: What do you do if your ex remains in your friend-group’s NFL Survivor Pool after a breakup?
  Should he forfeit, or is continuing okay?

• Jared and Jordana’s Take:

  • If participation is passive/on an online platform with no direct group chat interaction, it’s prudent for him to stay in.

  • If he’s actively engaging with her friends or in a chat, it might get petty.

  • They stress communication and emotional honesty:

    "Every time I see you make a pick in this group, it really makes it hard to move [on]..."
    (Jared Freid, 29:31)

  • Both agree breakups don’t mean someone vanishes from all mutual circles—but sensitivity is key.

7. Older vs. Younger Friendships: Creepy, or Normal?

Starts ~38:52

• Listener Email: Is it creepy for a man in his 50s to ask a woman in her 30s (former colleagues) to lunch?

• Jared and Jordana’s Response:

  • As long as the invitation is respectful and no pressure is applied, this is not creepy.
  • The age gap might unsettle some, but both are adults.
  • Key distinction: “creepy” is often just unwanted attention—the behavior isn’t inherently inappropriate.
  • Quote:

    "He asked her to lunch, which is like the most uncreepy... It's not like he was sending her dick pics."
    (Jared Freid, 40:22)

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Notable Quotes & Memorable Moments

• On pen pals and mixed messages:

  "I'm not texting guys that I don't want to date. That's why... I wouldn't just be texting a guy unprompted... if I didn't want to date him."
  (Jordana Abraham, 19:30)

• On men’s intentions:

  "Your version of 'not want to date' is not my version... I would text someone who I enjoy their company, I think is hot, and it's fun. There's no end game here."
  (Jared Freid, 19:45)

• On boundaries and clarity:

  "If you hate it, you're not confused. You're turned off."
  (Jared Freid, 12:08)

• On false intimacy:

  "There is this false sense of intimacy it feels like they're bringing, where—I'm sure there's been many women who think they're dating you and they haven't been on that many dates..."
  (Jordana Abraham, 08:38)

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Timestamps for Important Segments

• [01:18] – Main theme introduction; reaction to Bethenny Frankel’s TikTok
• [04:10] – Bethenny Frankel's full “pen pal” video
• [07:04] – Why 'pen pal' season comes back every fall
• [09:51] – Jared lists reasons men might be "pen pals"
• [12:46] – Advice on dealing with the pen pal dynamic
• [15:17] – Strategies for disengaging or clarifying intentions
• [18:10] – Mixed signals and their emotional toll
• [27:10] – "Petty or Prudent": Breakup sports pool drama
• [38:52] – Email: Navigating friendships/relationships with significant age gaps

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Conclusion

Jordana and Jared offer a nuanced, practical—often humorous—take on modern dating frustrations. They emphasize being honest with yourself and others about your intentions and boundaries, the importance of clear communication, and recognizing that sometimes, “pen pal” dynamics say more about what someone wants from you (or doesn’t) than what they’re willing to come out and articulate. Listeners are encouraged to decide what feels right for them, cut off energy drains unapologetically, and not overthink perceived “confusion” when usually, the answer is pretty clear.

Main Takeaway:
Be clear about what you want in dating, don't be afraid to set boundaries, and stop giving pen pals more emotional energy than they're willing to invest back. And never confuse respectful interest from someone older for "creepy" unless there's actual discomfort or inappropriateness involved.

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Transcript

[Jordana Abraham]

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[Jared Freid]

And welcome back to the Friday Feels episode of the U up podcast. I'm Jordana Abraham.

And I am Jared Freed. It is so good to be back here with you Jordana.

[Guest or Producer]

How are you?

[Jared Freid]

What's the haps?

[Guest or Producer]

What's going on?

[Jared Freid]

I am great. Things are lovely. I just watched the TikTok that you wanted to discuss.

Yeah, I, I sent you a tick tock that I watched like the first.

[Guest or Producer]

Five seconds of and never watched end of it.

[Jared Freid]

And you didn't watch the end of it.

I literally like well cuz I get annoyed. Can I, can I give you kind of how I feel with these tik toks that are about dating is like I'm like we did this. We did. We've answered this for seven years. So it gets annoying to me that like and it's stupid. I'm, I'm wrong. Can I just say I'm wrong. Okay, I'm wrong. But I get like personally annoyed that like we've given answer to these things and women are still making videos going, I'm just so confused why men have to be pen pals. And it's like first of all you're not confused. You're a smart woman who went to college, who started a business. I mean the one I Showed you was from Bethany Frankel.

Yeah.

Bethany Frankel is on. Is one of. She's not on Shark Tank to pitch her business. She's on Shark Tank because she's a fucking shark. Yeah. Like she's a billionaire and she's going. I'm just so confused why men are such pen pals.

[Bethenny Frankel]

Why are men looking for pen pals?

[Jared Freid]

It's like, stop being confused. These men are not stupid. They're not. And we've talked about this here for years. These men know what they're doing.

[Jordana Abraham]

They.

[Jared Freid]

There is a reason that you can figure out. I don't. I'm not a smart person.

Right.

And I know why they're pen pals.

Let's play the thing.

But I do understand. What I can't believe is that I'm smart. I can't believe I know the answer. And Bethenny Frankel, who I have a great respect for, I think TikTok's the worst and best thing that's ever happened to her.

Yeah. The worst thing that can ever she. How many videos does she make a day? I feel like everything in my feed is hurt.

I can tell you exactly what happened with Bevani Frankel. The worst thing that could happen to a mouthy is too much money talk. Is it? Well, because here's the thing. She's making money off of every video. So to her love and hate doesn't matter. Attention.

Talk is talk.

Talk is talk. So she keeps making videos. And Bethany loves making money. And these videos, she's probably making 50 grand a month. Wow. If you think about it.

Yeah.

At a min.

It's a lot of skinny girl margarita.

Right. That. That she's getting for just being her.

Right. Like, I mean, that's the dream.

Right. So she's getting the dream. Plus, so all these people are like.

Like, let's play the video so we can all be on the same page and hear it.

[Jordana Abraham]

Yeah.

[Jared Freid]

I invite. She follows me on tick tock.

Oh, wow.

We. We follow each other.

I would love for her to come on.

I invited her. I wrote in the comments of this thing.

I said she doesn't do anything unless she gets paid.

Doesn't do anything.

[Bethenny Frankel]

Why are men looking for pen pals? So you'll go out with someone one time, like each other. They like you. Takes a minute to get the second date on the board. For whatever reason. Sometimes they get a little stuck and they can't get the next plan on. And it's like sometimes it's so far between the first plan and the next plan. That you forgot about them. One person said to me, oh, you know, what are your plans in November? I'm like, I'll be dead in November. What are you talking about?

[Jared Freid]

November.

[Bethenny Frankel]

It's two years away. So they want to tell you their deepest, darkest secrets and what they're doing and every intimate detail of their day. I don't know you. You're a stranger. So until we are committed or I do know you, I don't give a fuck. Like, I'm not even trying to be rude. It's like, I don't really care until I'm invested in you because you're a stranger. So when you're not a stranger, when we've been out several times, when we've slept together, when we, you know, feel connected to each other, that's when I want to know your deepest, darkest fears and secrets. Until then, like, light and bright, because let's get another date on the board. Until I decide whether I want to invest in this, it's an investment of my time. Does everybody have that kind of time that they want to just be fucking around, texting some pen pal? Because I don't. I can promise you with every fiber of my being. I don't.

[Guest or Producer]

I hate this so much.

[Jared Freid]

What do you.

What do you hate about it? Because I don't. I don't see what's. What's so bad about it.

I guess my perspective is this is.

[Guest or Producer]

Tough talk for the sake of tough talk.

[Jordana Abraham]

Okay?

[Jared Freid]

Like, I. I don't believe that the men she's texting are just doing this naively, like, oh, they're telling me. They're like. And I also don't believe Bethany is this stupid. Like, for her to be like, you're telling me your every secret. I don't want to know your every secret. I want to go on a date. Oh, really? Single woman wants to go on a date? Didn't really. It didn't occur to him that you want to go on a date.

[Jordana Abraham]

You.

[Jared Freid]

He is playing his game. You're playing your game. Let's respect that. Both sides are playing a game, I guess. She's playing her game. She's going, I just want a date. I'm not going. She's. She's Miss Confidence, Miss tough Talk. But he, like my dad growing up, he'd always say, this is. This is the pep talk he give me. Ready? You're not that smart. You're not that stupid.

Okay?

Nobody and everyone you talk to, not that smart, not that stupid. We're all around the same. That's how I got pumped up before leaving the house. Okay.

Okay.

And I would say that to Bethany right now. Okay. I would say, bethany, get over yourself. You're. You're a successful woman who I. I love. I. I'm like, I, like, think she's fantastic, but when I see stuff like this, I'm like, bethany, the idea that, like, these men are telling you their deepest, darkest secrets over the text and they don't realize, oh, this date should happen.

[Jordana Abraham]

Men, right. Well, I don't think she's saying they don't realize, though.

[Jared Freid]

I think she's saying, like, this is my perspective on getting it.

Well, this is her, but I think she's saying, like, they're telling me these things, you know, as if I care. As if I care. And it's like they're telling these things to you for their own reasons.

[Jordana Abraham]

Right.

[Jared Freid]

But it can still be kind of annoying.

It can. Annoying aside, sure. I'm like, where are we trying to get here? Like, because her, she's not the only one. It's pen pal season.

Okay.

Right now. Because I've seen a lot of videos about pen pals. Why are men do. Men will just text and text and text and not make a date. You know why it's pen pal season? Because it's fall. There's less excuses. Summertime is the time to find your pen pals because there's built in excuses. I'm traveling this weekend. I'm going this place next weekend. I have, you know, dinner with friends. I'm doing this, I'm doing that. Now you get to fall when everyone redownloads the app. As we said, September 1st, everyone's redownloading, settling into where they live, where they work, into their schedules. And now there's less reasonable excuses. So now you are texting more with someone who should make a date. And the guys know that.

Right?

Why do men become pen pals? We allow societal things to be explanations for women in dating. We really don't allow societal things to be explanations for men a lot.

[Jordana Abraham]

So what's the.

[Jared Freid]

I would say, because growing up, women are scarce when you're growing up, you're told, be a man, talk to her.

[Guest or Producer]

They like it, approach, pursue.

[Jared Freid]

So when you get someone who will talk to you, a woman that will talk to you, you hold on to her like she's an acorn that you might need. When the snow gets, you know, when it starts snowing, but she's saying, we don't like it, it doesn't matter. She's still talking with the guy, then stop talking to him if you don't like it. That's the part that annoys me. She could just stop talking to him. Hey, this is enough for me. Goodbye. She could not answer or she's going, why does he keep telling me his deepest, darkest secrets? Like, okay, well then don't answer.

[Jordana Abraham]

Well, I do.

[Jared Freid]

I do actually think. And maybe you're guilty of this too. To spawn the discussion about it is like men will text you like you're your boyfriend and you've been on one date.

Right.

And there is this false sense of intimacy it feels like they're bringing. Where like, I'm sure there's been many women who think they're dating you and they haven't been on that many dates with you. But you guys text all the time.

[Jordana Abraham]

Right?

[Jared Freid]

And I do think that's like a. That's a thing where like, not everyone is always on the same page.

I agree. And I.

If you find a woman who's like who it does like it. And who is willing and is down and takes that as he likes me.

Right. And I text with people and I'm available for text and we'll go back and forth with you and I also can let go of that person. That doesn't mean that we're getting to know each other on this next level. Just because I've texted that.

[Jordana Abraham]

Well, they.

[Jared Freid]

Can you see why they might see it that way?

Absolutely right. I just think there's nothing that is in place of an in person meeting. And if someone's not making that in person meeting, there either has to be a really good reason or they're holding on to you for a rainy day. They're still deciding. There's a number of reasons a guy pen pals. There's one. They really like getting a text from someone. They're lonely and you're just someone. You're not the one. You're someone.

Just anyone. You could be anyone.

A text feels good to get, no matter who it's from. It's like a gift. You unwrap it. You find out what's in the inside to every.

You think like you like texts from everyone.

I'm not saying I never see a text.

And you're like, oh, of course.

But you'd rather have a text you go than never any text at all.

I guess I'm just saying sometimes I get a text, even from a friend, and I'm like, I have to answer this text.

I have to deal with it. It's a to do list.

[Jordana Abraham]

Yeah.

[Jared Freid]

I Agree.

There's actually, I think, more text that I don't want to get than that I do.

I would say the difference is text.

From someone who, if you're dating, it's different.

Who hypothetically wants to.

[Jordana Abraham]

Me.

[Jared Freid]

Yes. Different. Yes. I don't. I don't get as many of those. That many people.

It's been a while.

It's been a bit.

Yeah. That's what I'm saying. Text from someone who hypothetically wants to you is an exciting text to get.

[Jordana Abraham]

Okay.

[Jared Freid]

And you want to keep all options. Men love vague options. So they text and text and text all. Or the guy. So here's the spectrum of reasons. They love getting a text from someone that hypothetically wants to fuck them. Two, they're dating someone, it's ending.

So they're setting up their. Their next.

They're setting up their next victim. Backup, right?

[Guest or Producer]

Victim's probably the wrong word.

[Jared Freid]

They're setting up. They're setting up their next exciting attention. One person's pen pal is another person, and one person's pen pal is another person's guy who got weird.

[Jordana Abraham]

Sure.

[Jared Freid]

Because they're texting you, that means they're not texting someone else. So time is finite. They really are busy. They can't make a plan for now. And it's a little weird to be like, hey, it was really nice to meet you. I can meet in two weeks. So they start to text you and you're on the same phone as their parents and their sister.

It's kind of the most innocent version.

That's the most innocent. It has to exist.

Sure.

And then the other reason is they have no plan of meeting with you, but you're a hot chick who texts.

Them, and maybe one night they'll want to text you.

Late night, maybe. It happens. And now you're someone that is just a friendly, you know, like. So, like, this is all self preservation is my point. Like when you say, like, I'm con. I. I hate that these guys text me if you hate it. You're not confused. You're turned off.

Well, Jared, let me ask you. We'll give advice to Bethany, to anyone else who's wondering where to find this amazing advice. What if. If. If we went on it? We went one date. You are asking me my loose plans for a month from now, very busy month. And then you text me. Most days, you know, we're talking. I'm kind of like, I only met you once. I don't want to know if I want to keep talking for a vague date. That's happening a month from now, which, to be honest, you might cancel, right? There's like a 30% chance you can't. At some point. Sure.

[Jordana Abraham]

Yeah.

[Jared Freid]

So how do you recommend I deal with you?

I really, I would say if I were. If you're dealing with me, I don't think it would happen that way. I think we would go on a date and then the next day we're just texting. How's the day? Oh, my God. This joke you made last night, this reference you made.

Yeah, I'm doing, I'm going here. I'm doing that.

Oh, what's your weekend like? I got this coming up. Remember I told you I'm going traveling? When are you back? Well, I'm back next week. We should do something then. That would be like the normal progression.

Okay.

And if I'm dealing with someone like that and then they start texting me the next day, I'm dealing with it. I'm just like, oh, today's been crazy. Maybe. I like, you're saying if you're the.

Person, if you're the woman.

If I'm the woman. Because I do have a day in the calendar. If I had no day in the calendar, I'm just, you know, when I'm free.

You're not answering.

I know. I would say, hey, I'm, I'm game for next week. Just make a plan and I'm in.

You would say that to whatever non, non related thing he's texting.

Well, what's your plan next week? When do we get together again? If you said that like, like you get back the next day. Hey, how's your day?

[Guest or Producer]

Last night was so much fun.

[Jared Freid]

Would love to do it again. Hey, that sounds great. I'm free next week. Tuesday, Wednesday, Thursday. Make a plan and I'm in.

Actually, the next I'm gonna be you. I'm gonna be what you're dealing with. The next couple weeks are crazy. I'm traveling and then I've got like this work thing. I'm. I'm around the last week, the first week in November. We should do something then.

Oh, okay. So I would write back, oh, man. I guess we're on a month to month schedule. I'd make a joke about it. I'd be like, oh, man, I guess we're just like a once a month or something like that. Is it something stupid? I'd acknowledge, but with fun. Well, when you're ready, shoot me a text for a plan and we'll see if I'm free. But I think That's. I just think that's too.

Okay, then I. Then I say, will do.

[Jordana Abraham]

Right.

[Jared Freid]

And I want to go out with you. Or like, no, you want to go out with me because I'm you. Okay. And then let's say a couple days later, what's going on this weekend?

[Jordana Abraham]

How's.

[Jared Freid]

Or maybe I wouldn't say that because I.

[Jordana Abraham]

Because that would. How's. Right.

[Jared Freid]

How was that project that you handed in last week?

Project was good. This weekend I got. Not much going on.

[Guest or Producer]

I told you.

[Jared Freid]

Wish I could see you sooner.

I'm doing this, this, and this, and you got to check out this movie. It was so, like, I'm contin. You know?

I know. I know what you mean. I. I just wouldn't even answer.

I think that would just, like. I think that would. What would happen?

It could.

Yes.

But I'm just saying, like, why do they do that? They're trying to, like, soften you. This is.

You just would not. You would not answer. I don't know.

I'd have to be, like, so excited from that day. Like, I'm saying I'm. I'm seeing it from my end. Like, if I had a day with someone and it was like, fine, and then they're like, I can do this a month from now. I'd be like, I don't know. Like, I would kind of forget about it. Like, okay, I wouldn't.

If they're texting you, you're just like, not. If they're texting you, so you don't forget about it. Are you just not answering?

I guess I'm not answering, but I guess I'm trying to think of, like, when I've been in this scenario, and when I'm in this scenario, it doesn't feel as far away.

You've had dates that are, like, three, four weeks apart.

Yes, I have. But I'm saying it just doesn't to you.

It doesn't feel that way. Okay, so you don't mind the texting up and everything?

I really don't have a problem with it. That's the thing. I'm unbothered when they talk about, like, these pen pals, like, the. The person that is refer, like, the other side of that. The guy's like, that's just someone I'm texting.

Like, you're not. Like, I don't. Is there no part of you that's like, I don't want to fucking talk to this person about their week. I don't know them. Like, you don't feel any you don't relate at all to what she's saying about when you're speaking to a woman that you, a little bit.

Have only met once, right? A little bit, but not really.

You're, like, having fun.

I'm like, yeah, this is the fun part.

[Jordana Abraham]

This is the.

[Jared Freid]

Oh, no, I really. I relate much more to her where I'm like, I don't really care, like, about you visiting your niece this weekend. Like, I don't, like, really know you.

This is why I get annoyed with her, okay.

Because I'm not gonna say that to a guy who's texting me a picture of him and his niece.

Maybe you should. Like, I. Honestly, I don't give a. About your niece. We've met once.

Oh, my God, that would be so mean.

That's the thing. I'm revealing why I'm so mad at her. Because this is. This conversation is helping me because I'm like, I. I do see this. I. Because I saw a couple. It was, like, a young girl who was referencing the Bethany Frankel Ben Pal thing. So I was like, this is now a thing. I know why it's happening, because this time of year is pen pal season. Like, I know I'm right about that. And I just, like, I. I'm annoyed because I'm like, I don't care. None of these men.

[Jordana Abraham]

Right?

[Jared Freid]

Well, you're not dating.

Getting these men, you're not dating as.

A means to an end.

Right.

Is also the difference.

That's the difference. And when you say, like, when a woman says to me or, what are we pen pals? I am unaffected by that. Like, I. Yeah, I guess we are. Like, I. Like, as if. I don't know. As if I'm like, oh, better put away my pen.

And you're not. You're not offended?

I'm not offended. I don't. Fuck. Yeah, I'll keep writing you letters.

[Jordana Abraham]

Right.

[Jared Freid]

But she doesn't want the same thing you want.

I know, but I'm just saying, like, when you say the pen pal thing.

[Jordana Abraham]

Right.

[Jared Freid]

But I get annoyed at how. How much you've missed.

I see that.

Figured out my view on this.

I just do think. I do think it's like, it is. It is a. It is. I don't say annoying. It's tough when you're like, I actually do want to see this person for a second date. I want to keep talking to them, but I don't want to keep talking to them in a way that feels like it's going nowhere because I actually am looking For a relationship, that's the.

Most engaging person to deal with.

[Jordana Abraham]

Right.

[Jared Freid]

And this person is like, again, they're showing it.

[Jordana Abraham]

They're.

[Jared Freid]

They're.

[Jordana Abraham]

It's a.

[Jared Freid]

That's not exactly a mixed message, but it is a little bit. It's like you keep talking to me about your life, which in most scenarios in life kind of means you feel connected. If I'm telling. If I'm. If I'm going out of my way. And again, going my way is a loose term here. If I'm right, if I'm thinking of you to message you unprompted during the day, I will assume you feel like a connection.

Yes.

And I do too.

[Jordana Abraham]

But you're not really like.

[Jared Freid]

But I'm like. So I don't want to be like, I don't give a. About your niece, but I also would like a. Would like a date, but. Because maybe we have different goals here.

You just said. And something that was like a toss away. I'm going out of my way. But going out of my way is a loose term here. That's how all men feel. Like, when you're like, why are you texting me so much? I'm going out of my way. But what do I, you know, two seconds, text you back to maybe get blown, you know, like. And I know.

So annoying.

This enrages people when I talk about it. I know. This is why this hasn't gone viral because.

Because I'm not texting guys that I don't want to date. That's why. It's because I'm thinking about the way you're thinking the way, like, the way I'm thinking what I'm thinking. I wouldn't just be, like, texting a guy unprompted in the middle of the day to ask him about his. His weekend or his night if I didn't want to date him.

So I'm like, your version of not want to date is not my version of not want to date. I'm saying I would text someone who I enjoy their company, I think is hot, and it's fun. It's not. Again, there's no end game here.

Right.

Well, that's the difference around, you know, my end game isn't as specific as maybe the end game of the person who's, like, annoyed with the pen pal.

Right.

Which is like, the whole point of this conversation.

Yeah.

You are dealing with someone you. I'm so confused. Why do men want to be pen pals? Men don't care about the subject. You really care about you know, they don't care about the engagement, the wedding, the move in. That's not. When they're texting you in this phase of things, especially this phase, they're not even there.

[Jordana Abraham]

Right.

[Jared Freid]

So you're dealing with someone who's playing a different game than you.

Yeah, I just think it's a difficult, like, I think it's a difficult conversation to have because it's kind of like, again, you don't know each other that well, so you're not going to be like, I want a second date, or, I'm not talking to you.

Right.

Because then you sound crazy. Yeah, right. Because then you sound crazy. And you could hint at it, but it's not always so, like, black and white. Like, there is a lot of time where it's like, I'm actually really busy the next. And how. Again, you've done this all the time. Or like, we've talked about this. When. When I set you up with that.

[Jordana Abraham]

With.

[Jared Freid]

With the friend of a friend that you didn't. That you were like, she's not texting enough between the dates.

Right.

And this is almost like a great.

Example of that because it's a fine line.

Right. Where she's like, yeah, I don't want to just text someone who's not interested in, like, really dating.

Right. But especially if you're, like, making the date, you're going on a second date, you want to be excited for that second date.

[Jordana Abraham]

Yeah.

[Jared Freid]

You want to feel like you're connecting in some way.

[Jordana Abraham]

Right.

[Jared Freid]

I think it's. I think it's a little. It's a little more complicated in some ways, just to call out. To call that person out, or to like, to ask for what you want when it does feel like a lot of the excuses people give are valid. He is traveling. He is doing that. Like, how do I. How do I discern between someone who's actually busy and really does want to date and really does want to see me versus someone who's just, like, texting to text?

It's very complicated. I agree. But I think when I hear the people that are like, why do they want to be a pen pal? At that point, I'm like, you don't like this person? You don't want to text? I don't think that's true, but I do think it's true. I mean, for you, I'm not wanting.

To text with people that I do like, because I'm like, I don't want to just be. I'm looking for. I like you, but I'm also looking to date you.

I'm not looking to, but I would assume that anyone I'm texting with that I'm having a good time texting with. And again with a plan, like, coming up. Like, you know, when you have a plan coming up and texting in between, I think that's, like, a different thing than idly texting with no explanation of when the next plan is coming.

[Jordana Abraham]

Sure.

[Jared Freid]

And I think idly texting with no explanation of when the next plan is coming is easier to be, like, asking for a time.

[Jordana Abraham]

Right?

[Jared Freid]

Like, that's it. But if you have a time and it's far away, I can see where it's like, what is like, I'm. And you might cancel. You know what I mean? It's like a little more vague. It's a little more. You're in the in between.

But I just like, yeah, I. But at that point, you can go, hey, this week's totally. Which is hard to do. This week's totally busy. We got the back.

Turn it around. Them.

Yeah, yeah, I'm busy, too.

I'm excited to see you.

Right.

But to see you three weeks from now. Let's circle back.

I think that, that, that those two are. No matter what.

Yeah.

I'm so excited to see you three weeks from now. Unless there's, like, a plane ride involved, right. You're screwed there. Like, I don't know. I. I just. I've been. Every time I see these videos, I'm like, like, why are they doing this? Men, like, options, right? Like, why?

Well, it's because you're monsters, right?

[Guest or Producer]

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[Jared Freid]

I love Hungry Root.

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[Jordana Abraham]

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[Jared Freid]

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[Guest or Producer]

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[Jared Freid]

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[Jared Freid]

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[Jared Freid]

Let's do petty or prudent.

I like this one.

Petty or Prudent. Also, if you're in Richmond, Virginia, I'm there this weekend and then D.C. next weekend. Come out to the shows. Chicago, Milwaukee, Minneapolis, all coming up. And San Diego, Orlando. I'm doing the whole conch. Come on out. Assemble the group chat. Let's go.

Head out there. Hey, J and J, can you help.

[Jordana Abraham]

Me determine who is petty and who is prudent?

[Jared Freid]

Here I participate in an NFL Survivor.

[Jordana Abraham]

Pool with 15 of my friends.

[Jared Freid]

Basically, each week we pick one team to win a game, then cannot pick that team again for the rest of the season. If you get two losses, you're out of the pool and whoever makes it longest is the winner.

[Guest or Producer]

Survivor pools are fun.

[Jared Freid]

That sounds fun.

[Jordana Abraham]

I would do one, even though I don't even.

[Jared Freid]

I don't even. Like, I feel like you could not be in the know that much.

All you have to do is just pick random teams, right? Yeah. And, like, I mean, obviously there's better picks to make. You can figure that out. But, like, it's fun with anybody.

Yeah. All right. I'm gonna do this next year.

[Jordana Abraham]

Yeah.

[Jared Freid]

I invited my boyfriend of two and a half years to join, but we broke up about two weeks ago around week three of the NFL season. How many weeks is the NFL season?

Eighteen.

Oh, my God.

Yeah. That's early.

Yeah.

But survivor pools run up quick. People like, you know, fuck up.

I'm sure.

Yeah.

Sounds like he didn't, though.

No.

Because he is still making picks even though we've gone fully no contact. My girlfriends and I are frustrated by this. I do not really take this pool seriously at all besides some friendly competition. But my ex works in sports and is an NFL fan. He is only connected to this group through me and does not have any Independent friendships in this group. Jared, as a football fan yourself, what do you think? Should he continue participating in this or take the l on the $20 buy in and go away? If he wins the money at the end, should I send him a Venmo request for it? I know that would be very petty. Thank you.

I love this email. Same petty or prudent wanting him to.

[Guest or Producer]

Just stop doing the league.

[Jared Freid]

I think they're. They're both being like a petty off. Almost like, if I were her, I would have her friend or I would do it herself. I would Venmo him $20. That was his buy in and be like, I think we need to separate.

I think she's being petty.

I think she's being petty by not just sending him money. She's like, should he just eat the $20? I'm like, you should just eat the $20 and, like, pay him to go away.

Right. I guess the vulnerable thing would be like, hey, every time I see you.

[Guest or Producer]

Make a pick in this group, it.

[Jared Freid]

Really makes it hard to move me.

I mean, they were in two and a half years, long time.

But that's why it's like. But also, I think she's being petty.

[Guest or Producer]

Where it's like, your boyfriend exists on earth after you guys break up.

[Jared Freid]

Like, he should leave the group, though.

[Jordana Abraham]

Yeah.

[Jared Freid]

But if you're. This is like, the thing is with a survivor pool is if he wins, like, the more you like Carly's. I know, but it's like, the more you win, like, you're in. Like. I just think it would never dawn on me that I have to, like, not put in my picks for the NFL week because I broke up with my girlfriend in the league with all of her friends. I also don't think that she would see it, like, he's not being petty doing this. Like, I don't think he's, like, putting in his picks, thinking that she's seeing that.

I guess I don't know how it works. Is it like you. You send it to a group chat.

I would assume you send it to the commissioner, whoever's, like, involved, who's, like, in charge of this league, and it's not her. Now if it's.

If you say there's a group chat.

If there's a group chat and you have to be like, a New England.

[Jordana Abraham]

Yeah.

[Jared Freid]

Like, don't you think that's weird? That's how I pictured it. Like, he's like, texting, like, this week I'm taking, blah, blah, blah.

I would think it's done online in my opinion, I'm not in a Survivor's pool. I think this is great. This is.

Sounds really fun.

Yeah. Especially because it's two losses. So you get two chances to lose each. You know, usually a Survivor pool is like whoever is like still around, like it's one loss and you're out.

Right.

So this is meant to keep people playing for longer throughout the season.

You don't think there's like a group. There would be in this case scenario? Like all I see in Mike's bonus pop ups is like pops pop ups from his fantasy league where the group text where they're talking about.

This is a bit different.

You don't think there'd be like a group text where people are like talking about the.

Sure. But I don't think he has to be active in that to be involved in the league. Like, okay. She seems annoyed that he is actively living and breathing, like based on.

[Jordana Abraham]

Around her.

[Jared Freid]

Around her.

[Jordana Abraham]

Yeah.

[Jared Freid]

And that she has to see him. It's like, I don't know. I guess it's like someone watching your stories after they've ended it.

I think it's different because it's her friend group.

I think the stories is worse.

You think?

I guess it's her friend group. But also like if he's putting in the picks without her having to know. Like if she's like just seeing that a pick.

We need more details.

Right.

[Jordana Abraham]

Like if.

[Jared Freid]

If it's like she goes to the website where the league is and she sees he's put in Carolina and she's like, I can't believe he's still putting in bets. That's kind of on her.

Fine.

If he's texting the group chat being like, saints minus three got my pick in.

What is minus three?

Men like the Saints to win by three. Okay. Like if there's no line Survivor, if.

He'S actively involved in her friend group chat, I think that's.

That's one where he could be like.

Petty on his end.

I'll give up the 20.

Yes.

Yeah. But if it's an online platform where she just happens to see that he's put in his pick, I can't really see how that's like her. That's his problem. Because I would assume, like when I put in the pick, I would like be like, it's. It doesn't really touch her.

[Jordana Abraham]

Right.

[Jared Freid]

And he actually, if it's like the way that you're saying, I agree with you. Because if it's. He has to put it online, it would almost be Worse for him to not do anything.

[Jordana Abraham]

And then someone has to reach out.

[Jared Freid]

To him to be like, you didn't put in the pick.

Right?

Where he's like, I'm gonna like, just make the con. I'm gonna like do everything I need to do to make sure there's as little contact as possible. I'm just putting in the pick and going on about my day as opposed to like, I'm not doing anything. And then they have to be like, this guy, this guy who broke up with our friend is holding us up.

Right. And also, boy, he won't. He's. He won't even like, must been a bad breakup. He won't even like, he ditched.

He seems petty.

Yeah. Like, I think like keeping everything steady is like the move again.

Yeah. Again, assuming there's no. He's not in any.

There's no group chat because you could just put in this pick without even.

[Jordana Abraham]

What if he asked?

[Jared Freid]

I wouldn't even think that she would know.

What if he has to text her best friend to let her know his.

Yeah, that's. I think that's out then too. I would be like, I'll give up the 20 bucks.

[Jordana Abraham]

I think that's fair.

[Guest or Producer]

That's fair.

[Jordana Abraham]

Yeah.

[Jared Freid]

But like the way she writes it to me, I. I guess I read it.

I would text the. Yeah, if it was the she had text friend, I would just have texted the friend. Hey, I'm sure you heard about the breakup. I think I'm gonna pass on the.

[Jordana Abraham]

Rest of the leak.

[Jared Freid]

Right. You can send a personal text, but if it's like an online platform, do.

It to just not right.

[Guest or Producer]

My girlfriend are frustrated that he puts in his picks.

[Jared Freid]

Like, come on, like I'm right.

What is the frustration?

[Jordana Abraham]

Just that.

[Jared Freid]

That he exists. Yes, I agree.

He'd be if he didn't. Also, he wouldn't be a good look either way.

Damned if you do damage. You don't. But right now, considering if it's an online platform, prudent. If it's not and it's a group chat that he has to text. Petty.

I'd also love to know more about the breakup. Like, would this all be different if he cheated on her? Can he still make the picks if.

He cheated on her so he can win that money to take out his new girl?

Like, does that. Does the breakup reason matter?

I think, right. Like, this is two and a half years.

If it was two and a half.

Year relationship that didn't work out. It sucks, but like, it didn't work out. Like, right.

Well, that's what I'm wondering. I think I need, like, I need, like, a little more details on, like, clearly they thought they would be together for the season or he wouldn't have committed to this.

Well, I would.

You would commit to it?

Even if I was like, I don't know, like, you still have to act like you're in this relationship for three.

Weeks, I guess, right?

Like, let's say you were gonna break up.

[Guest or Producer]

You're like, I'm doing this.

[Jared Freid]

And then it's like September. And she's like, let's do the pool. And you're like, I guess we'll do the pool.

[Jordana Abraham]

Right?

[Jared Freid]

I guess you're not resigning a lease.

[Guest or Producer]

Hey, how about we don't do that pool?

[Jared Freid]

Why?

[Guest or Producer]

I'm just not feeling it. I don't have $20.

[Jared Freid]

Like.

[Jordana Abraham]

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[Jared Freid]

I'm excited that Audible is releasing a.

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[Jared Freid]

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[Jared Freid]

Bill Nighy and Glenn Close as Lady.

[Jordana Abraham]

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[Jared Freid]

It is like so cute and it's extremely comfortable.

[Jordana Abraham]

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[Jared Freid]

All right, let's do an email. J and J. Big fan of the podcast.

[Guest or Producer]

I have a weird situation I'd like some insight into. I worked for five years with an older guy who recently left for a new job. He's in his late 50s, I'm in my early 30s. He's a super outgoing person and loves to joke around and have fun. I tend to vibe with that person because they bring me out of my introverted Shell. So I always had fun talking to him and we had playful banter. I knew he was kind of a player and had dated some women a bit younger than himself, but not anything crazy, so I never thought anything of it. I came to really value our friendship at work and was sad to see him leave. Recently I ran into him at an event we picked up like nothing had changed. Just having fun, giving each other a hard time. The next day he texted me and told me he really misses me and wants to go to lunch sometime. I assumed he meant platonically, but my best friend who sort of knows him freaked out and told me he was being creepy and just wanted to get in my pants. Once she put that in my head, I got paranoid and ended up blowing him off in kind of a rude way, which I felt guilty about. I saw him again and he was still nice but things were awkward. What do you think? Was my friend right? Do older men ever just want a platonic relationship with a younger woman?

[Jared Freid]

Here's my thoughts on this. Let's say he did want a non platonic relationship. She's not 18, she's in her 30s.

[Jordana Abraham]

Right?

[Jared Freid]

It's not like that. It's not like so messed up for a man in his 50s to ask out a woman in her 30s.

I'm happy. I don't think that's not me. I had this. I don't think I had the same read.

I don't think it's creepy. It's not like he was sending her dick pics like he asked have happened. Yeah, he asked her. He shot his shot, asked her if she wanted to get together and again, this is. This is. It might not be about dating. Probably is. And I think if it is, she might be like that's too old for me. That's fine. But I don't think asking a 30 something year old woman out as a 50 something year old man is like a huge crime.

I had the same read as you. I totally agree. It annoyed this email annoyed me. I like the friend annoyed me. I know they say the friend put freaked out freaked out.

What is there to freak out about?

That a man wanted to date a woman. Like right? Again, the ages matter.

Yes.

She's in her 30s, he's in his 50s. So what it's and this is where that age gap that's happened. It happens in a world. It happens. And the age gap thing is only weird to the people who make it weird for you.

Right.

You know like this in a world of things happening, this happens.

If she was like, I'm 21 and he's in his late 50s. I might be like, this is like a little bit of a stretch still. Like, I guess look at what's his name, Bill Belichick. It happens.

We all judge.

Yeah, right.

You know, but the judgments don't mean that we have to like, own those opinions as our own.

[Jordana Abraham]

Right.

[Jared Freid]

And what will the world think? I totally get that insecurity. Like, if you ended up dating, like, oh, what will people think?

[Guest or Producer]

Yeah, that's an insecurity you're allowed to have.

[Jared Freid]

I. I'm with you. I don't like to vilify this guy. This is kind of like one of those emails that if I saw it as like a tick tock, it would really like. It kind of like it. It would really like ruin other tick tocks. Because again, you said something very important. He didn't creep her out.

[Jordana Abraham]

Right?

[Jared Freid]

He. He has been respectful based on this email in every way.

Yes. If you were gonna, if he, if he was interested in her romantically, this would be a perfectly normal way to express that.

Hey, I miss you. And you know, I think it's sometimes funny that we're like, well, he's older, he can't be feeling the same thing as me. Like, she's like, I have fun. Every time we see him, we like hit it off right away. Like a 50 year old man can also say, you know, we really hit it off. And she like, I'm funny. She brings out a side of me where I'm funny.

Right.

And we have this great back and forth. Like, and, and listen, if she was into that, that's great. And she probably wouldn't even think it's creepy.

That's what I'm saying.

Creepy is only, you know, attraction away, you know, like it's.

Yeah, I agree. And I don't think, I think, I mean, like, there would be an age where it would be creepy. I think that she's past that age.

Right. And that I think anyone over 30.

That'S asked out by anyone over 30 is creepy.

I agree. And, and that's the thing. Don't, like, what are the. What's the word for this?

[Guest or Producer]

I'm not really a wordsmith.

[Jared Freid]

Like, infantile yourself.

Like, infantilize yourself.

Like, you're in your 30s, you're not, you're not Lizzie McGuire anymore.

Right?

You know, like, like grow up. You know, like, it's like, right. That's the part of this email that I annoys me is like, listen, we all. I'm 27.

I assume he was looking for a date.

I assume that too.

[Jordana Abraham]

Right.

[Jared Freid]

I, I.

Which is again, but also, he asked.

You to lunch, which is like the most uncreepy of like, it's not like he was like, let's do drinks at the top of the empire.

He said, lunch sometime.

Let's do lunch.

Sometimes I. I come back to my. Come back to my apartment.

Right. There's, like, on the levels of, like, what he could have said that was so horrific.

Yeah.

This is, like, so far from creep that you're ruining the word Cree.

Yes. He playing. He's playing the only thing less creepy would be coffee. But he's playing it, like, extremely safe.

Right. And. And I do understand she is valid for being like, the minute it was put to me that way, I was like, oh, I don't see him that way.

Which is fine.

Totally fine. That's like, totally. I, I've, you know, we've all way where, like, you see something from a different angle and you go, o. That's not.

Yeah, I'm not looking to do that.

Right.

And then.

And if he was to reach out and then she said she was rude to him. Yeah. I don't think you should be rude to someone. But, like, also, like, I get it. Like, oh, it's changed things for me. I don't want to go out with them, and I didn't know how to handle it.

Right. But I think the word creepy is not applicable.

Not.

[Guest or Producer]

Listen, you're.

[Jared Freid]

You're. It's. It's demeaning to real creeps.

I agree.

So we solved dating again.

We did it. Proud of us. We'll be back next week.

Boom.

Bye.