How Your Dating Profile Is Keeping You Single

Summary

U Up? Podcast Summary

Episode Title: How Your Dating Profile Is Keeping You Single
Hosts: Jordana Abraham & Jared Freid
Release Date: March 5, 2025

Episode Overview

In this episode, Jordana and Jared dive into why your dating profile, prompts, and app behavior might be the very reasons you’re still single. They share their takes from both genders' perspectives on what makes a profile stand out (or flop), breakdown the psychology behind app interactions, and answer listener emails about dating dilemmas ranging from “meet-cutes” to situationships, texting dynamics, and the dangers of putting minimal effort in your dating app persona.

The hosts blend their trademark humor and candor, unpacking topics around effort, vulnerability, the desire to be pursued, and classic dating confusion—giving practical, honest advice to help listeners navigate modern love.

---

Dating Apps: Are You Selling Yourself Short?

[12:34–19:10]

• Jared’s App Experience: Describes matching with someone who left their prompts blank, explaining men’s typical rapid-fire swiping approach.
  • “If you want to know how men are swiping, they're swiping differently than you.” — Jared [12:57]
• Importance of Prompts: Both hosts agree that completely blank profiles suggest the person isn’t actually invested in meeting someone.
  • “As someone who … hasn't written a prompt or bio, that is someone who doesn't want to be there. They're putting the minimal amount in.” — Jordana [14:52]
• What Makes a Good Prompt?
  • Light, personal, and a bit vulnerable
  • Prompts should make it easy to start a conversation, not just show off
  • “You're giving someone a chance to answer you in a fun way. It's not about you sounding fun to them. It's about them seeing what you wrote and writing to you.” — Jared [15:18]
• Photos & First Impressions
  • Photos that are too revealing might attract the wrong kind of attention; profiles should reflect the kind of relationship you seek
  • Pro Tip: Cheating the “half-second swipe” with revealing pictures brings more attention, but not necessarily quality matches

---

The Pursuit Dilemma: Who Should Make an Effort?

[16:43–23:42]

• Desire to Be Pursued vs. App Realities
  • Many women want to be pursued but resist putting energy into apps, expecting men to work harder
  • Jared: Pursuit is good—but you need to engage with the format to get results
    • “If you want it to be exactly like it would be in person, you need to get off the app.” — Jordana [18:33]
    • “You're still on a dating app...if it's not going to work out exactly how you want it to work out in person, don't be miserable here.” — Jared [18:21]
• The Dangers of Half-Effort
  • Half-done profiles and “playing it cool” strategies lead to frustration and missed connections

---

Texting, Tone, and Awkward Dynamics

[20:06–24:00]

• Awkward Texting Explained: The hosts discuss how mismatched energy or unclear intentions can sabotage early-stage relationships.
  • “What I don't like to hear is ‘I'm a bad texter.’ We are a bad texter.” — Jared [20:34]
• The Golden Rule: A bad texting dynamic is rarely about technology, and more about lack of investment or honesty
  • If someone is genuinely busy, they’ll explain; if they don’t, ambiguity is a red flag
  • “Not texting is not a bad texter. It's not acknowledging what's going on in the texting.” — Jared [21:54]
• Match the Effort: Deliberately vague or cold responses are usually pride or ego-driven, and signal unbalanced interest

---

Key Listener Email: “Is This a Real-Life Meet Cute?”

[28:18–39:48]

Situation: Listener meets a woman by chance (she mistakes him for a blind date). He tracks her down via LinkedIn/Instagram. Should he reach out?

• Hosts’ Advice:
  • Reach out, but over-explain how you found her — transparency is key to avoid coming off as a creep
    • “He has to act like he is an accused predator...Just understand you are a predator and you are, you know, start with fear...admit to everything.” — Jared [35:15]
  • Be explicit, concise, respectful, and one-and-done (no follow-ups if unanswered)
  • If she’s interested, she won’t be creeped out—what matters is attraction and context

Notable Quote:
“Creepy is only attraction away.” — Jared [34:49]

---

Are We Dating? Situationships & Labels

[43:34–57:56]

• Listener Email: Summer situationship with ongoing trips; “Are we dating?”
  • Hosts’ Analysis: No—if you’re always meeting on his terms (vacation, trips, never in his “real life”), you’re not dating.
    • “She is full alleyway cat. She's an alley cat.” — Jared, on the difference between “main street” and “alleyway” relationships [48:33]
  • Advice: Stop “tasting all the flavors”—set a boundary: “I want a real relationship or I can’t keep doing trips.”
    • “You've tasted all the flavors you can taste at the ice cream shop.” — Jared [52:36]
  • Reveal how you feel and require a commitment for things to continue—otherwise, the cycle will not change

---

Is “I’m Confused” Code for “I’m Turned Off”?

[58:14–71:58]

• Listener Email: After an amazing first date and subsequent lackluster communication, is she being back-burnered?
  • Hosts’ Take: She’s not imagining things—if you feel let down by someone’s effort, honor your disappointment
  • One thoughtful reschedule is fine, but perpetual lack of momentum is a sign they’re not as invested
  • Practical Strategy: Next date, see if the spark remains, then invite him to a group hang to create “momentum.” If he resists, you have your answer

Notable Quote:
“It's okay to be like, I'm a little turned off by this. But we'll see what happens Wednesday, right?” — Jared [66:24]

---

Quick Bits, Memorable Quotes & Reddit-Style Game Segments

On Finding People via LinkedIn

“LinkedIn is the greatest database of people you're trying to go on dates with.” — Jared [33:38]

On Half-Hearted App Participation

“It's almost worse to be on [dating apps], half doing.” — Jordana [19:09]

On Dealing with Red Flag Profiles

• “If this person's hot, we'll push through and see what happens. If I'm attracted—I’m more ...” — Jared, on dating profile deal breakers [86:06]

On Red Flag/Deal Breaker Scenarios

[74:13–86:41]

• If someone double-questions your response time (“???”) on the app — hosts agree: deal breaker
• If a man keeps a “piss pot” by the bed to avoid walking to the bathroom — deal breaker, both laugh at its absurdity [81:20]
• If someone’s dating app prompt says “You should NOT leave a comment if you’re a vegetarian” — red flag, unnecessarily negative wording

---

Tone & Atmosphere

The episode features classic U Up? banter—playful, candid, occasionally irreverent but always practical. The hosts draw from their own experiences and listener stories, balancing empathy for modern dating frustrations with no-nonsense, actionable advice.

• Jared’s take: Offers the male dating psychology and calls out commonly ignored truths, never afraid to be blunt or self-deprecating.
• Jordana’s take: Brings the thoughtful, empathetic, and often strategic female perspective, keeping advice grounded and realistic.

---

Episode Takeaways

• Dating App Success Is About Effort: If your prompts or bio are blank, you’re signaling you’re not truly present—it’s better to be off apps than “just pictures.”
• Show, Don’t Tell: Good prompts are light, personal, and vulnerable—invite conversation, don’t just list facts.
• Don’t Play It Too Cool: Being “pursued” is fine to want, but you need to play the game to some degree; minimal effort yields minimal results.
• Transparency Wins: When reaching out after a chance meeting, lay all the cards on the table—be explicit with context.
• Situationships vs. Dating: If you’re never integrated into real life, always traveling or hiding, you’re not dating. Set boundaries and require commitment for escalation.
• Text Matching Is Real: If communication feels off, inconsistent, or unbalanced, it’s okay to move on; matching energy matters.
• Red Flags in Prompts & Behavior: Overt negativity or impatience on apps is a sure sign of a mismatch—don’t ignore your instincts.

---

Memorable Moments & Quotes

• [16:33] “She wants you to do a lot of work.” — Jordana, about women leaving prompts blank but expecting pursuit
• [22:40] “If one person's exclamation point and emojis and like giving you a little bit of, doing a little dance … are you going to match that energy or not?” — Jared
• [35:15] “He has to act like he is an accused predator … admit to everything.” — Jared, on how to properly DM a “meet-cute” woman you found online
• [52:36] “You've tasted all the flavors you can taste at the ice cream shop.” — Jared
• [86:41] “You've chosen negativity over positivity.” — Jordana, about negative app prompts

---

Final Thoughts

Don’t underestimate how much your dating app effort and profile energy reflect your genuine readiness. If you want to be pursued, show up and invite it. If you crave a relationship, insist on being someone’s “main street,” not their “alleyway.” And—when in doubt—never ignore the energy mismatch in text or real life. The right person will meet you where you are.

Transcript

[A]

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[B]

Work, they all say that they're friends and I'm like, I can't imagine making a friend at 39 years old. Like I, I actually can't. Like at this point in life, I'm like, I avoid all maybe friendships everywhere.

[A]

Yeah. Your next friend is going to be your wife. Hello and welcome back to the podcast. I'm Jordana Abraham.

[B]

And I am Jared Freed. It is so good to be back here with you. Jordana. How are you? What's going on? What's the haps? This is coming out on 3, 5, March 5th. We're in March.

[A]

We're in March. If you're wondering why we're not talking about Jared's Australia trip, because that's where you currently are. That's where I am pre recording a lot. We're good. You're going to get the full recap when he comes back.

[B]

I'll have my nervous breakdown once I'm back, as I do when I come back from trips abroad. Those are the best episodes we make sure to schedule. The minute I get back, I walk off the plane directly into the studio. I'm like, you have been doing, doing that. I've been doing that a lot. Yeah. Rachel Konnell. That's what I, I did the Same thing as her. She gets broken up with. Straight to the studio to tape the response. That's what I do. I go straight from my flight to New York.

[A]

Hardest working man in America.

[B]

That's right. So, yeah, we're getting ahead so that I can go to Australia and tour. If you're out there on the 5th of March, I've already. Sydney sold out.

[A]

Wow.

[B]

I'm an international star.

[A]

Impressive.

[B]

That is.

[A]

Congratulations. That is very impressive.

[B]

Thank you. And thank you, the listeners, because everyone's a part of this. I'm going to be in Brisbane tomorrow night, and then I'm gonna be in Adelaide, Perth, and then I come back. I'm doing some New Jersey shows. I'm doing Rochester. I'm doing Nashville. The beat goes on. So jaredfree.com. so I am in Australia now. I'm enjoying, you know, my Australian tour. But what's been going on? What's happening?

[A]

What's happening? I'm fresh off my steakhouse dinner.

[B]

You had a big steakhouse. Drunk fest.

[A]

Drunk fest. And then we had a little bit of a glitch because it was. There was a huge snowstorm.

[B]

I missed it. I was in Florida for it.

[A]

I heard you.

[B]

I mean, I heard it. It got a little nasty.

[A]

Yeah. We got many inches, which, again, in the city, different ball game than on Long Island. We couldn't get an Uber. None of the Ubers were driving that night because it was. The roads were very, very bad. I was, like, a little worried even once we got into the Uber. But it was like we were kind of like, are we going to have to sleep here? Because everyone was, like, trying to get an Uber on their own, and none of them were working. We were calling taxi companies. They were like, no, one try tomorrow. We were like, I guess, are we sleeping at this fucking restaurant? And then we're like, try tomorrow.

[B]

I think we'll be.

[A]

Yeah, I think we'll figure it out by then. And then finally someone gets one and it says, like, it's 25 minutes away. And this is, like, at the restaurant is, like, closing. And they are, like, so annoyed that we have taken an Uber there and we cannot get there. Like, we've got to get home as well. We would love to leave in this snowstorm.

[B]

Also, the hostess isn't such a host at that point. They're like, okay, come on.

[A]

All right, get the fuck out.

[B]

Yeah, they were nice before. More bread, more wine. Oh, you guys are the best. Then 10 minutes after, you want to go, like, get the fuck out of here.

[A]

Yeah. And long Island. I mean in the city things are open super late. This was like, yeah, probably 10, 15. And they were like, we have got to leave.

[B]

Snowstorms, you know, that's, that's tough stuff. And driving in that, that's scary. And but you know, this, this episode comes out March 5th. We are thawing. We are heading into period. This is the time of year that dating. I think we're heading into peak dating season. We're past Valentine's Day, the darkness of winter. We're heading out. There's like that one random nice day that you're like, maybe I will go for drinks afterwards. Maybe I will meet someone new.

[A]

That'll come soon. That definitely hasn't happened yet. March 5th. But maybe by we're heading towards that.

[B]

Like we're like two weeks away.

[A]

Yeah. From like that one nice day.

[B]

Yes. The one nice day that like randomly happens and then go back. Someone's like snowstorm.

[A]

Did you hear it's going to be 62 on a week from Tuesday.

[B]

Right. And for the people in Arizona, they're like, what? This is every day for us. I, I But it is just that time of year that people are starting to come out a little bit more. I just think it starts now. So the awakening on the dating front, that's a, that's exciting for the people listening. If you're maybe kind of down the dumps a little bit.

[A]

Are you going to be dating in Australia?

[B]

I think I, I've, I, I, I where it's summer. I, it's gonna be summertime.

[A]

No excuses for you. It's gonna be summer there.

[B]

I'm gonna go out, I'm gonna meet people. English speaking country.

[A]

That's true. You know, and good sense of humor.

[B]

I feel like also partying. I, I think they're like kind of like they're like a going out people.

[A]

Well, you know, Australia is made up of British criminals.

[B]

I've heard this.

[A]

Yes. This is where they, that the UK used to send all of their criminals to Australia.

[B]

Boat ride.

[A]

That's the pop. That's why the pop. That's like that. Why they're English speaking. That's like the population really.

[B]

So when you went there, could you feel that? Is there like a pride in that? Is there like a, you know, I.

[A]

Felt like there was a, the criminal error. No, no. I don't know. I don't, I don't feel that really at all. But it does feel like there's like a little bit of like a, an outback, like a little bit of a Venturous and a little bit of a daring, adventurous kind of. Kind of.

[B]

I like that. So, yeah, I'm excited. I. I mean we're going to see. I mean, if you want to follow on Instagram.

[A]

New Zealand too. Do you have shows in New Zealand?

[B]

One show in New Zealand in Auckland.

[A]

So how's that show doing?

[B]

I think it's me and the wait staff at this point. I. Well, I'm sure you'll find Sydney than Auckland.

[A]

I mean, Sydney's like there.

[B]

New York, right?

[A]

Big city. Yeah.

[B]

So I'm excited. It'll be more stories to come. I was just in Florida. I was on the apps. I was.

[A]

Got a good tan.

[B]

Browsing. Got a tan. I got a little burnt. It was a ten of a beach day. I mean like we went to the beach and it was like, this might have been the nicest day of the year. I know. I hate to tell you. I know how much this affects me.

[A]

You know how February gets to me.

[B]

I mean this was like. We were out Super Bowl Sunday, which is like my favorite holiday of the year, winter Thanksgiving, and just we're sitting out golfed, tanned.

[A]

Who's we?

[B]

You and my mom, my dad, my uncle was there, myself in the ocean. Out of the ocean. It was just one of those days.

[A]

That you're like, you guys just spend all day at the beach. What time did you get there?

[B]

We got there at 10am, 10:30 in the morning.

[A]

Can you order food?

[B]

You can. We can order food. We. We go to a place where you can get some food. Yeah, it's a full service establishment that my parents, like, they made the right decision when they got there. They like set themselves up, they got a nice house, they're at a club and then they have like a beach situation.

[A]

Yeah.

[B]

That is like the most luxurious.

[A]

Like, so they don't need to go on vacation. They live in, they live on vacation.

[B]

When they go on vacation, they're going like the same place that they live in.

[A]

Right. That's what I'm saying. Do they go on vacation?

[B]

Yeah, they go, they go away. They like, you know, they go travel. They've. They've done. I mean, my parents have been everywhere. Like, it's like, it's actually crazy. Like I. My grandmother used to go on world cruises and she would go around on a cruise around the world and then there were legs. Sometimes she'd be on her own. She had like a boyfriend that worked on the ship. Like, she, he was like her.

[A]

Okay. Did you know him?

[B]

No, my parents did. Like there Was like her friend who worked, worked on the ship.

[A]

Like you might be a little bit more like your grandma. She sounds very independent.

[B]

She's very independent. My grandma. Yeah, she.

[A]

Your grandmother's body too?

[B]

Same body. We have the same tits. So Grant, my nana, she, she would love. She was a pain in the ass similar to me. A lot of complaints. And then she would go on these cruises for three week legs. My mom and dad would join her. So they've like seen the whole world with her. They used to like go on vacation with her.

[A]

So it was like she spent a year on these cruises.

[B]

It was like a long time. Yeah. Like, like, I think it was her, my grandfather, literally, her and my grandfather's like, dream where like to own a place on this world cruise and then like just go. And then my grandfather died and it kind of changed the plans and then she ended up doing it and then my parents would like, meet her. So they're like, it's funny. Like, they'll have pictures of like on the great wall. And it's just like my mom and dad and like this old, little, old, little old lady.

[A]

I mean like your mom's mom or your dad's mom?

[B]

My dad's mom. So it's like they, they've been so like, I'm going to Australia, New Zealand. My dad's like, New Zealand's just like Boston. And I'm like, what is it?

[A]

That's what everyone says.

[B]

That's what he said. He goes, it reminds the harbor and you know, the fish and chips are pretty good. Like, he had memories and like, so they've done all of this stuff. I don't think there's a place they haven't been.

[A]

Did she even have a home or was she just living?

[B]

She had like a very, yeah. Modest apartment, like in Florida. Just like to keep.

[A]

Right.

[B]

It wasn't like a, a this is later.

[A]

Sounds like you guys have a very similar lifestyle.

[B]

We do. Yeah. She was never one to want, like when grandfather died. Never wanted to like, date again. Never wanted to like, meet anybody.

[A]

Didn't she just date this, this guy working?

[B]

They weren't dating. It was like more like a.

[A]

Hooking up.

[B]

Yeah. They just, he'd go down on her, get her off.

[A]

I mean, you said like it was a guy who worked on the.

[B]

Yeah. It was dating.

[A]

I don't know.

[B]

Maybe I'm making this up. I gotta ask my parents. I, I, we don't talk. We don't. You know, your family.

[A]

It's interesting because you, I have vague.

[B]

Memories of stories we don't. We don't know our history. We don't know who moved here. We don't know the immigrant tale you.

[A]

Really don't know anything about, which is just funny to me because I feel like you're good at asking questions. Like, I tell a story, you ask, like, I'd like to, a lot of good, interesting questions. And then I'm like, well, why'd your mom get divorced? You're like, I have no idea. I would never ask that.

[B]

I don't know. We don't. Yeah. Even. Like, I was with my family just now. Like, I flew in this morning from Florida. It was my dad's birthday today. We were just like, no history. No real history. We don't really get into it.

[A]

Sounds like you could use Storyworth.

[B]

I mean, we really could. If they want to sponsor. No, I. I walked into the. I. I. Sometimes I just end the conversation. I walk in the kitchen, my dad's shooting up his Ozempic, and my mom's like, you should be doing that. And then I'm like, all right, goodbye. Gotta go.

[A]

That's my cue.

[B]

Time to go. I think I've been here long enough. And we got in the car, and my dad's like, you know, he's wondering what. They're wondering what I'm gonna do as far as my living situation is concerned. And they're like, you know, you gotta start looking. It's a lot. And I'm like, yeah, it's a lot of work. I gotta, like, figure this out and.

[A]

Go on a world cruise. Think you should tell them that idea?

[B]

To them, hey, want to go cruising.

[A]

About going on a world cruise?

[B]

I tried to get them to come with me to Australia. They're like, too long a flight. No, can't do.

[A]

It does become a certain age. I feel like, where people are like, I'm not sitting for that long.

[B]

No, I mean, I'm not looking forward to the flight. 22 hours.

[A]

I mean, there's a piece of me.

[B]

That looks forward to it, and there's a piece of me that doesn't. Like, there's a piece of me that's like, great. I can be alone with my thoughts and be on a flight, but then there's a piece of me that's like. I was told, I think Michelle Wolf, the comedian, my friend, she said that, like, hour 15, you're like, what, the.

[A]

Time to get off?

[B]

Yeah, yeah, yeah.

[A]

Is it direct?

[B]

Direct from LA to Austin.

[A]

Okay. You got a little break.

[B]

So here to la? Yeah, I'm I'm excited for you. Yeah. And I had a. I had a situation on the dating apps. I got. I wanted to talk about this.

[A]

Let's just. Let's break it down.

[B]

So I was on the dating apps, and someone had nothing written for their. They had answers. No answers to any of their prompts, but they were hot. This. And to take you inside the mind of a man, like, you know, these dating apps. I don't mean to be gross, but when you're. If you want to know how men are swiping, they're swiping differently than you.

[A]

Yeah.

[B]

And I've been writing a lot about this lately because I'm writing the book. The book is. Is on my mind. And we did this whole section on dating apps, and I'm writing out, like, how do men swipe? Or how do I swipe? Or what should you do for your picture? And. And it's like, you have to have a picture that speaks to a man.

[A]

In half a second, but not speaks to him too well, in my opinion. Well, because then you attract the wrong kind of guy.

[B]

You are what you is again, you know, if you're. If you got your boobs out, you know, and you're in a big bikini, and again, that's going to draw the half a second. You. You're. You're kind of cheating the half a second, so to speak, you know, instead.

[A]

Of going, right, but are you getting. Are you getting. You're definitely getting more guys that way, but are you getting the guys that you're looking for?

[B]

Exactly. That's why you're cheating the half a second, because you're. You're just going to get guy. Like, there was even a Super bowl commercial that was like, all about breast cancer, and the whole commercial was like, ooh, titties. Did you see that commercial?

[A]

No, I didn't.

[B]

It was a. Did anyone see the commercial? It was like this whole premise of this breast cancer commercial was like, men looking at tits. And it got my attention, and I'm.

[A]

Like, what was the message?

[B]

Help women with breast cancer. I don't know. I just know that there was titties everywhere. And maybe we could.

[A]

They add, say, titties.

[B]

It's a crazy ad that turns into. At the end, you're like, oh, I was here for breast cancer all along. Good for me. You know? Like, I. So I think men swipe the dating apps like that too, where they go titties.

[A]

Okay.

[B]

And then just like. And ask the questions later. So, like. But if you're like, again, this is all to say, like, everyone is someone's type. Everyone. We are all here on Earth because we, we have, our, our lineage has survived. So someone wanted to. Your mom and your grandma and the deckhand was going down on my grandma on the cruise.

[A]

All so that you could be, you.

[B]

Could be here, here yelling at you. So to my point, I guess this prompt had nothing written. But I like when the prompt's written because to get to notice, I can.

[A]

Say as someone who at first, when dating apps came out or when I, I'd been on dating apps where I haven't written a prompt or haven't written a bio, and that is someone who doesn't want to be there. They're there because they, because they feel like they should be, but they really don't want to be there. So they're putting the minimal amount in.

[B]

I totally agree. And I would say if I'm to give like advice out there or to say the prompts should be written so personally so, you know, with like, fun, you have to be light, personal vulnerable. Yeah, light, personal, vulnerable. Those are the, to me, that's the key to a good prompt response. Because what you're doing is okay. You're giving someone a chance to answer you in a fun way. It's not about you sounding fun to them. It's about them seeing what you wrote and writing to you. Again, I'm looking for better matches. So like, if someone writes like, you know, my, my typical Sunday and they write something like, well, I wake up at two in the afternoon because I go out too late at night. Like, at least they're telling me what they do. And I can say, where would you go last? A little self deprecating. And I can say, where did you go last Saturday night that you were out till 2am what was this weekend's, you know, Saturday of choice again? It gets us rolling.

[A]

Yeah.

[B]

You know, at a running start as opposed to nothing. So I wrote to this person, I go, you have nothing written here. You know, I, I go, I go, there's no, no prompt for me to respond to. What do I even say? And I'm being playful with the fact there's, there's no prompt written. So then it became hot. You should say, hey, what's up? So then I wrote, hey, what's up? And then I wrote in parentheses, I go, thank you for the help. And then like, I think I'm playful with what I'm given.

[A]

Right. Well, she wants you to do a lot of work.

[B]

Well then they wrote back lol and I wrote back, is that what's happening this weekend? Like, I'm just trying to, like, get a conversation going and I.

[A]

Pulling teeth a little bit.

[B]

And I think there's this. And we were talking about this interaction and you were like, there. You were saying how much women do still want to be pursued.

[A]

Yes. And I think that that's a. I mean, we've been talking about this a little bit or a lot this, this month. Just this idea of, like, you know, you're on a dating app or you're somewhere where, like, the idea of going on a date is sort of implied. How do you do that? Go on the apps, be there even though you don't want to be there and still be pursued on something that's sort of taken away, the pursuit. And I think some people are like, I'm not going to be putting a huge amount of effort into this dating app because I'm. I'm then even giving them even more. Like, they should be pursuing me. They should be. They should be, like, earning these quippy, whatever or probably completely normal, bland answers. Like, I'm not going to give them anything. If they like how I look, let them. I'm just going to give them enough to make them do more work.

[B]

I know, and it's a thin line. Like, like, listen, let me just say as a, as a man, I don't think a woman wanting to be pursued is a bad thing. Like, and I agree with everything you just said, the app kind of takes away the romance of being pursued. Like, it's all implied. I totally. So let me first give anyone who's wondering, like, avoid saying that they want to be in that they want to be pursued. Like, you are allowed to feel that, to want that you should. Again, I'm not gonna tell you what you should or shouldn't want, but if someone said, I want to be pursued on the dating app, I would go, yeah, I think most normal men know that.

[A]

Okay.

[B]

Innately.

[A]

Right. So they're like, how much do I. How little can I give while still getting that pursuit?

[B]

And the thing is, you, I think you always have to admit where you are in the atmosphere. You are still on a dating app if it's not going to work out exactly how you want it to work out in person.

[A]

Well, that's the thing. If you, if you want it to be exactly like it would be in person, you need to get off the app.

[B]

Right. Just don't be miserable here. Like, if you're in gym class and we're going to Play dodgeball. You got to play dodgeball, right?

[A]

Like, I don't want to get hit.

[B]

You're out. You're out. Like, you're just going to sit on the side. Like, don't get involved. To, like, oh, you hit me. I'm out. Like, that's not even fun.

[A]

I totally. I totally agree with that. I used to do the, like, just pictures, no bio, no whatever on the apps. And then that didn't work for me. And, like, that's probably partly why, like, I might as well have not been on them.

[B]

Right. It's almost worse to be on them, half doing.

[A]

I agree.

[B]

Because you're just getting angry, right? You're just like. And again, this person kind of got angry at me because I'm, like, trying to get this conversation going and they're. And I felt badly. Like, I don't. I don't want to anger you. I'm. I'm, like, trying to. Hey, what's up?

[A]

Like, you were trying to be fun, but maybe she was a little sensitive.

[B]

Listen, Misunderstood. That's okay. Lost in translation. That can happen. I just think this idea that. Well, how do you.

[A]

How do you be pursued then?

[B]

I don't know. You know, you have to give in to the stupidity of it. It is stupid to be on the apps. It feels dumb. You have to be okay with. Feel like doing the. I don't know. I see this a lot. This seems to be the theme this month because we're seeing a lot of, like. And it's probably the time of the year where we're seeing a lot of, like, are we texting? Are we not? How much texting should I do? We have a couple emails today that kind of, like, center on this. I think you said you have. You said there's an article for batches that you guys did.

[A]

There was an article that I think I wrote back in, like, again, 2012 or 2011 or something, and it was one of. And it was called Awkward texting dynamic.

[B]

Yeah.

[A]

And it's sort of just like when the. The texting between, like, two people just, like, is. There's, like, something missing from the flow of it. Either, like, one person's being, like, sarcastic and the other person's not picking up on it.

[B]

Right.

[A]

Or one person's being really enthusiastic and the other person's, like, not matching their energy, and it's just, like, you're not vibing.

[B]

What I don't like to hear is I'm a bad texter. We are a bad texter.

[A]

Okay.

[B]

We don't Go.

[A]

But if I'm answering you in a timely fashion and you're not, am I?

[B]

We, we are not the match. I think, like, it's okay.

[A]

We have a bad texting dynamic. Sure.

[B]

I think this is like, where we get where problems occur, where people push too hard for a date that maybe they shouldn't go on.

[A]

Sure.

[B]

You know, you go. We can't figure out this texting thing. What do we think? We think this is going to get better on the date.

[A]

Right.

[B]

We think, you know, just because. And I, I, I know I'll get a response to like, no, I'm bad at text. You are until you're not.

[A]

Or here's the thing. I think you can be bad at texting if you explain yourself. That's still, you could be bad and still have a sense of what the other person's looking for.

[B]

You can get ahead of it.

[A]

Like, that's what I'm saying. Like, you could be busy. You could, you could be texting someone who has a really busy day job who isn't, doesn't have time to text you all day or isn't interested. But for them to say that, I think is totally fine. But to say nothing, Right? There's no, you don't, you don't have anything to go on. You don't know the person. You don't know what they're like. You don't know if they're actually, if this means they're, they hate you or they're interested.

[B]

Well, let me go back at you a little bit. Not texting is not a bad texter.

[A]

Okay?

[B]

It's not acknowledging what's going on in the texting. So just like you said, like, it's not that you didn't answer, it's that when you did answer, there was no, like, hey, I'm away from my phone all day. Cause I work, you know, on the stock exchange, and they make me put my phone at my desk and I'm buy, sell, buy, sell. Funny money. Boom, bah.

[A]

Sure.

[B]

But then saying, but Thursday night we should get together. Like, that's a different thing. Thing than, hey, how was your trip? And then you write, good, good, right? And it's like, okay, friends, right? And you know, this whole thing, like exclamation points. I used to do a joke, A girl that I was dating, I said, happy birthday with no exclamation point. And I thought she was like. And she got mad at me. And she's right.

[A]

I would get mad, right?

[B]

She's right. Like, if one person's exclamation point and emojis and like giving you a little bit of doing a little dance, right? And it's a little, you feel a little stupid doing the dance but like the other person has to see, like they're giving you an energy.

[A]

An energy.

[B]

Are you going to match that energy or not? And, and if you choose not to because you don't want to give too much and you don't want to, you don't want to, you know, you don't want to look like you're, you know, like that's a, A lot of this is pride and ego.

[A]

You think for men, all sides.

[B]

I think this is genderless. I think the, the, you know, I don't want to give too much because I don't want, you know, it's. I don't want to pan the day because I don't want them think they could take advantage of me forever. I don't want to tell, you know, put an exclamation point because I don't want them too excited. It's like, well, sometimes you got to be. You got to fake it a little bit. Sometimes you got to show that you are excited to get the other person excited, right.

[A]

And you have to know how much you're giving and when to use the punctuation. Correct. It sounds so stupid, but like something a delayed response needs an exclamation point, right? So sorry, I just saw this. Right? Yeah.

[B]

Like I.

[A]

You can't respond. Who are you there with? Friends, four hours later with no follow up and think that that's going to get you anything.

[B]

Right? It's a little too cool for school. It's a little. I gotta be cooler than you, right? So that you kind of want me. And to me that's like trying to judge up someone pursuing you, right.

[A]

Or trying to make a statement about how you are no longer as in as you used to be. As your what the Happy birthday. No exclamation point.

[B]

Oh, I'm not, I'm not into this anymore.

[A]

Yeah. Why did you do that?

[B]

Right? I was lazy. I was lazy. And yes, she's not my wife.

[A]

So you want. You're not that invested, right? So.

[B]

So I don't know. Let's get into the episode. What are we talking about today? Over sharing. Everyone's got to go listen.

[A]

Go listen. You can Watch us on YouTube or on YouTube now. Go listen. Go subscribe if you want some bonus episodes ad free day early and subscribe to this episode. Watch on YouTube. Subscribe on YouTube. We appreciate all our benefit subscribers, we've got two bonus episodes every month.

[B]

I mean, we really got into it on benefits.

[A]

Oh, yes. You want to hear? Jared and I have a. A little bit of a disagreement. I don't know, Civil discourse.

[B]

Civil discourse, yeah. Call it a disagreement. I. I think it's an interest. It's interesting. All these subjects are the reason we like this podcast is because we like talking about it. Like, we talk about it off air the same way we talk about it on air. And I think it's really difficult to, you know, put words to a lot of these things that really don't have an answer.

[A]

Right. Because they are very nuanced. And I think that's sort of the beauty of a format of a podcast is you can get into what the little things mean, because sometimes they do mean a lot. And anyone tells you that you're overthinking it, like, probably isn't, hasn't done it, or doesn't understand it, you're overthinking it.

[B]

Is the most annoying response to like, hey, so I'm dealing with this person I'm dating. It's like, okay, so I just shouldn't tell you the story.

[A]

No, it matters.

[B]

Yeah. Matters.

[A]

Yeah.

[B]

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[A]

I am a huge Rakuten user.

[B]

You're a user.

[A]

I have the widgets, I have the app. I don't buy anything without checking if the store is on Rakuten first. And I'm making sure I'm getting my cash back. You know, I love a deal.

[B]

You do love a deal. Way more than me. You're. You're a deal hunter.

[A]

Bargain hunter.

[B]

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[A]

Some of that's mine.

[B]

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[A]

Your hands are full or your eyes need a break, but you still want to escape into a great story? That's why I'm such a fan of Audible. I listen all the time. Whether I'm on a walk, commuting to the office, doing chores, or even just relaxing before bed. Audible's app makes it super easy to jump right into thousands of audiobooks anytime, anywhere. I've mentioned before that one of my favorite movies is Pride and Prejudice, and I'm excited that Audible is releasing a brand new audiobook version of the Jane Austen novel on September 9th. Narrated by Marissa Abela, Harris Dickinson, Glenn Close and other stars you know and love, Audible gives me the best of both worlds. I can enjoy a story I love while actually getting stuff done. They have thousands of titles, everything from romance to thrillers to memoirs, comedy and even self improvement. So whatever mood you're in, there's always something fresh and exciting waiting for you. And the app is super user friendly. You can download audiobooks to listen offline, adjust the narration speed, and pick up right where you left off across all your devices. If you've never tried Audible before, I can't recommend it enough. It's the easiest way to bring incredible stories into your everyday life. Trust me, once you start listening, you'll wonder how you ever went without it. Your first great love story is free when you sign up for a free 30 day trial at audible.com UUP.

[B]

Let'S get into the episode. What are we talking about today?

[A]

All right, I will read our first email. Hey guys, I'm a 30 year old guy living in New York City.

[B]

Dudes, dudes, dudes.

[A]

I've been single for a long time, but I've been dating on and off in the city without much real progress. Lots of first, second, third dates, but nothing really going Further tales Oldest time.

[B]

There it is.

[A]

Recently I was meeting up with a girlfriend.

[B]

I like how he wrote that.

[A]

Like a girl dash friend. So it's not his. Not his girlfriend.

[B]

I've never seen it written that. Yeah, girl dash friend.

[A]

I would write like female friend. A friend who's.

[B]

I kind of like how he did it.

[A]

All right, sure.

[B]

Girl dash friend. Female female friend. I would be like do protest too much. You know, like it's a.

[A]

A friend with a.

[B]

How would I describe You a friend.

[A]

With a vagina met up with Jordana.

[B]

My vagina friend.

[A]

Yes.

[B]

Ah, that's fun merch. Vagina friend.

[A]

There you go.

[B]

Yeah.

[A]

Great. For the platonic friendship. Who I've known for more than three years. We went on a few dates back when we first met, but mutually. The romance never took off and we have since remained friends. Cool. I made as a reservation at a small tea shop in the West Village one night to meet up with her after work. I ended up arriving about 20 minutes early. And I was. As I was waiting, I noticed a young cute girl peering into the tea shop. What? Peering in?

[B]

It is a weird way to write it.

[A]

Yeah. Clearly she was looking for something come.

[B]

From peering in that window there.

[A]

Right. Are you not visualizing, like, someone putting their face against the window like this? Yeah.

[B]

I'd be like, what is she looking for? Yeah, it sounds very like it's out of like a storybook.

[A]

Yeah.

[B]

And a young woman came peering through the tea shop window.

[A]

Should do some calm sleep.

[B]

The lion. The Witch in the Wardrobe.

[A]

You should do. Are you gonna do your audiobook?

[B]

I'm. I do want to do the audiobook.

[A]

You should.

[B]

I. I mean, I gotta make sense. I. That's where I would shine.

[A]

Of course. Yes.

[B]

This is my. You know, that's my love undercover. Love undercover. Do some VO work.

[A]

Yeah. Clearly she was looking for someone. And her and I made eye contact a few times. They used to call this the eye back in the day.

[B]

Oh, I do remember that. That girl was eye me.

[A]

Yeah. Yeah, the Gen Z's don't use that anymore. Maybe it's a little too.

[B]

It's a little aggressive. It is aggressive. Finally, chick was I me? Yeah. It is saying it.

[A]

Yeah. Now it seems, like a little gross.

[B]

Yeah. I'm gonna bring it back. What if I brought. I'm gonna bring it with me to Australia. Put it in my backpack.

[A]

Honestly, it's a good term to describe what it kind of means. Like this chick is I me making eye contact. Finally, this girl.

[B]

The out of this chick.

[A]

All right.

[B]

Yeah, it sounds bad for that angle.

[A]

Finally, this girl. Did you wear glasses? Eye condom.

[B]

Don't worry. War protection.

[A]

Finally, this girl walks in and introduces herself to me. Turns out she was on a blind date and thought I was the guy.

[B]

That makes more sense for why she's looking at it.

[A]

Peering in. Yes. Obviously I wasn't. And we joked around about it. We chatted and flirted. Felt like flirting to me. At least for 15 minutes while we both waited for our respective people to show up. No awkward silence, just continuous authentic conversation. She was so cute and chatty, I just couldn't help but think, is this a real life meet cute? Or is it just the novelty of meeting someone naturally in person in 2025? Eventually our track came to an end and we went about our nights separately. The next morning I was able to find her based on some of the information she gave me that night. It didn't take much. My question is this, is this really one of those times where you pursue someone or do you just let it be what it was just a random interaction in the big city. Grateful for your potted. Thanks so much for making dating content fun.

[B]

Before we get into this, you know what is a not spoken about but is like the true hero of searching for someone that you want to go on a date with. LinkedIn.

[A]

You've met someone on LinkedIn?

[B]

No.

[A]

No way. You're on LinkedIn.

[B]

I'm. I am. I think I am from like when I sold life insurance, still an account. LinkedIn is like how I find most women I've matched with.

[A]

Oh, like when you Google search them.

[B]

When you Google search, this is like.

[A]

The best click their profile because they.

[B]

Can see when you click it. Well, I don't have a profile. I don't. I'm not signed into my LinkedIn.

[A]

Okay, well then does it show you anything?

[B]

Nobody. You go to Google search and he says it's not hard to find her. It is very easy to find anyone if you have their job, their school, first name, New York, the city they live in.

[A]

LinkedIn, you can find a lot of information about someone on very little information about them.

[B]

Right. I just don't think LinkedIn knew that like a side product of what they do would be the ability to find a woman that you want to fuck.

[A]

So you're looking at women's LinkedIn profiles. I look all the time.

[B]

I have searched so many LinkedIn profiles, it's like crazy.

[A]

Can you have a good versus bad LinkedIn profile?

[B]

I only see the picture because I don't click on it. Just like very professional picture. Usually it's always a professional picture, but it's always like it gives me the last name.

[A]

Right.

[B]

So you search LinkedIn. New York City, you know, Sarah, NYU.

[A]

Okay, you have, right? Depends on their last name based on.

[B]

This 15 minute conversation. That is all LinkedIn information. That those five things can be found through a 15 minute totally.

[A]

No, not weird that he's able to find her based on.

[B]

Not weird that he can find her. But I'm just saying it is interesting to me that LinkedIn is the greatest database of people you're trying to go on dates with.

[A]

Right.

[B]

And they have no idea. Like, I don't think that company knows that. Like, a lot of their traffic is just randos coming over from Hinge trying to figure out who they're trying to.

[A]

Right. Well, what do you. What information do you find out from that? Just their job.

[B]

Last name. Last name. And then we back to Instagram.

[A]

I see. Okay. So just using LinkedIn to find the last name.

[B]

Yeah.

[A]

Okay, interesting. Who knew you were like catfish.

[B]

Catfish.

[A]

Nev. Shulman.

[B]

Is that how he. Oh, he looks people up like that.

[A]

Yeah, he has a special methodology. He Googles their name.

[B]

Yeah.

[A]

And that's it.

[B]

Okay. Guy's a genius. So to this question, what do you think? I. I do think it's funny that they wrote it's a novelty to like meet like this in 2025. This is like every story pre 2007.

[A]

Yeah.

[B]

You know, like.

[A]

No, it's great. I think, I think he should definitely reach out. They had a great in person interaction. She's single. She was waiting for a date. First date. So she's not like on a date with someone she's been dating.

[B]

Right.

[A]

He thought she was cute. They had a nice conversation. She didn't have to keep speaking to him after that. If I had that interaction and someone messaged me and I was into them, I would not be like, creeped out by it.

[B]

Well, also, creepy is only attraction away. So we do know that she is attracted to him because she said, you look like the guy I'm supposed to go on the date with, who she's.

[A]

Agreed to go on a date with.

[B]

Right. So we are pretty positive she finds you attractive. So that means you coming out of the woodwork isn't as creepy as if she wasn't attracted to you.

[A]

Do you think he should mention that.

[B]

He, like, has to mention.

[A]

Looked her up?

[B]

He has to act like he is.

[A]

Admit everything.

[B]

He has to act like he is an accused predator. He has to act like he is on the run and he knows it. There's like, you know, just understand you are a predator and you are, you know, start with fear, Right. Understand the fear that can come over someone being approached by someone out of the blue that they met for five seconds and you found out all their information. It's a little naked feeling. And if they're not that attractive or they feel a little. A certain type of way, which people are entitled. Entitled to about randos. Looking them up on the Internet via their LinkedIn, like I'm doing.

[A]

Yeah.

[B]

Then you have to understand that that could be a little weird. So I think going, you know, messaging her on Instagram, which is like a really kind of a. A good route, I think.

[A]

Yeah.

[B]

Hey, I know this is incredibly weird.

[A]

What if she's private on Instagram? Can he follow her and then message her?

[B]

I would message. No follow.

[A]

Can you message without someone who's private?

[B]

Yeah. Let's go based on. You can.

[A]

Sure.

[B]

Because I do think you can.

[A]

Okay.

[B]

I've had people message me that don't follow me.

[A]

But you're not.

[B]

I delete every single one.

[A]

You're not private.

[B]

That's fair. They are.

[A]

Yeah, but can you message someone who's private if they haven't messaged you first? Like, have you ever. Without following them.

[B]

It'll be like a message request.

[A]

Without following. That's what I'm saying. Without following them.

[B]

Without following them. Yeah.

[A]

You sure?

[B]

I'm positive. I'm positive. You can send that message and I think you don't follow. Send the message and just. Hey. I know this is incredibly weird.

[A]

Yeah.

[B]

We met and then explain where you're coming from. We met. Don't. No. No one knows you. This happens to me a lot.

[A]

You.

[B]

I know you. We met. No, no, no, no. Explain everything explicit. Get it down on paper. Hey, I know this is incredibly weird. We met the other night at the tea shop when you were peering through the window looking for your date. You thought I was them. I had a really nice conversation with you. It stuck with me in a way that I went and searched a couple of things you mentioned in our conversation. And I would love to get drinks with you if you're up for it. With a rando that met you in a tea shop. Like, admit to everything.

[A]

Yeah.

[B]

All out there. And I'd love to get a drink. If you're free Tuesday at 9. Here's my number. Yes, please text me.

[A]

Nothing wrong with that. Yeah.

[B]

Right. Like, I think like.

[A]

And that's it.

[B]

You're right. But that's it. You can't. Yeah. You can't.

[A]

Hey. No follow up.

[B]

Did you see this?

[A]

Yeah.

[B]

Bump.

[A]

Yeah. Don't. You don't do LinkedIn and Instagram.

[B]

No. 1. One. They saw it. And if you don't get back to. They saw it.

[A]

Right.

[B]

They saw it. It's a no.

[A]

A maybe's a no. A no's a no. No answers a no.

[B]

Everything except a yes.

[A]

Yes. Exactly.

[B]

That's a good policy.

[A]

Yeah. And I don't think that would be weird at all. I think he should do that, right?

[B]

And I understand his. Like, I'm seeing all these fucking articles. I saw an article, it made me eye roll so much. I'm so sick of articles, of articles. I'm just so sick of the politicization this, this, like, I just think everyone's just such a. What is the article? It was something along the lines of, like, men can't leave the house anymore because of the ick. And it's like there's, you know, young men are so fucked up by the ick that they don't even go on dates anymore. They're afraid of their own shadow. And it's like, no, they're not. No, they're not. No, they're not. And if they are, someone had a.

[A]

Deadline and needed an idea.

[B]

Tata.

[A]

Yeah.

[B]

Like, well, deadline. It's either clickbait, right? Or if there's one person they interviewed that's like, I can't leave the house. Well, say goodbye to that guy. Yeah, he ain't going to fuck. Goodbye.

[A]

Here's the thing. You just have to say, am I being a reasonable, normal person in this interaction?

[B]

Is it reasonable?

[A]

Yes.

[B]

To admit that. Yes. It's weird that I'm doing this.

[A]

Yes.

[B]

That. Here's how we met over. Explain.

[A]

Yes.

[B]

I can say it from my position because I. I know it more than most because I get people that all the time remember me.

[A]

No. And I'm like, to anyone. That's annoying.

[B]

Yeah, I hate remember me.

[A]

Right. I hate assume I don't remember you.

[B]

You message with your sister. No, I don't.

[A]

I would say you probably don't remember me, but here's how I. Oh, my God. Here's how we met.

[B]

You probably don't remember me. Makes me, like, kind of erect. Like, when someone says that I am so Puts you at ease. Oh, I'm like, I feel good. I'm like, thank you. Thank you so much. This is how much people can really just crush you. You remember me, right? Like, it's so different. Like, I'm like, I don't know.

[A]

We met.

[B]

We met.

[A]

You know me.

[B]

We talk, you know, come up. We talk all the time. Or I know you don't remember me.

[A]

Right?

[B]

I do that. I do that all the time. I. I do that. I do. I do it so much that, like.

[A]

I would say you probably don't. I know.

[B]

No, I. I know you don't remember me. I know you know, I'm a big loser. I. I have A small penis. Yeah, everyone hates me. No, no. Let me explain who I am. I. I will go above and beyond to make someone not feel that likes right over explain.

[A]

But go do it. And again. That's it.

[B]

That's it. One and done. Bring her to another tea shop where she can peer.

[A]

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[B]

It is funny that whenever I hear women talk about the Skims product line, they do kind of like glow a little bit about it.

[A]

It's just really hard for women to find stuff that looks good on you and also like is really comfortable. I think that's just a universal struggle by many women.

[B]

I just love when we have a sponsor that helps our audience. It's nice to know skims is like helping people feel better about themselves.

[A]

Yeah. And I am. I am a believer. I am a convert. I'm a skims gal. Recently I got the Fits Everybody full brief, which is like their regular underwear which I am wearing all the time now. It's my favorite pair. I get annoyed when I wear it because then I have to wait until I wash all my underwear to wear it again. You just don't think about it, which is the number one thing for underwear for me. I also have the bralette. It's a game changer. It lifts, it looks great. Super flattering, super cute, just the right amount of support. And also incredibly comfortable. I haven't always loved bras. Who has? But with skims, they are changing me into a bra lover. Shop my favorite bras and [e-mail] after you place your order, make sure to let them know we sent you select podcast in the survey and be sure to select our show in the dropdown menu that follows that.

[B]

Okay, let's do an oh, we love this game. Are we dating?

[A]

Love Are we dating?

[B]

So listeners write in with a scenario and they're asking, am I dating this person?

[A]

Yes.

[B]

And it's kind of like, we'll tell you.

[A]

We'll let you know if you're. Sometimes you think you're dating but you're not.

[B]

Probably not. But also, you know what this is. Are we dating? You're like, well, how could someone not know that they're dating someone? Like is like a a fair question. It is to know what rights you have to talk to someone, to say things to someone. Like, I think that's part of this game, right? Is like, who do I come? Where do I get to come off?

[A]

How much? Right. How invest. How intimate is this relationship?

[B]

Right? So we're gonna tell you. J and J subscriber here that can't get enough of the pod. Finally deciding to write in. Well, welcome. Thank you. Long story short, ish. I have. I had a whirlwind summer fling with a guy while on vacation for about a month. We both have vacation homes in the same place, have been friendly for a couple years, but never really hung out until this summer. Although I did try to hang out with him the the winter before by strategically going to Jared's show in the this guy's city. We didn't end up getting to see each other, but the laughs from Jared were Worth the five hour drive.

[A]

All right, now you're just buttering me up. Yeah, seriously.

[B]

We finally got together this summer and really hit it off. We basically dated for a month. We were together. Dinners, drinks, late late night hangs. The whole deal including being grown ass adults. Sneaking around our families trying to hook up like a couple of teenagers.

[A]

Cute.

[B]

Jump to the end of the summer before leaving to go to our respective hometowns. And I bring up the what are we? Conversation.

[A]

Yeah. Are you listening to the show? We say we don't. Don't do that reveal.

[B]

Whenever someone has the what are we? Conversation and they listen to the show. Yeah, I'm convinced they just don't want.

[A]

The answer because they know that that's not how you suggest doing things.

[B]

Right. They. They just know we leave it as a let's keep in touch and see what kind of solution.

[A]

This guy's good.

[B]

This guy.

[A]

What are we? We are people who will definitely try to keep in touch.

[B]

Cool. Sounds good. See you next summer. Right? Yeah.

[A]

She doesn't even realize what move was pulled on her.

[B]

Right. We leave it as let's keep in touch and see what kind of situation. Because we live so far away from each other. But said we'd plan some visits.

[A]

A lot of weeds. She's definitely thinking of them as a we.

[B]

Well, here's the other thing. It's so funny. Let's keep in touch and see what kind of situation we. Because we live so far away. It's like you say you can't have like 30 excuses.

[A]

Right?

[B]

This is like a mishmash of 30.

[A]

Excuses are all lies. One excuse could be the truth.

[B]

Yeah. Just like throw and yes.

[A]

See which one sticks.

[B]

Get out of here.

[A]

Right?

[B]

Get out of here. With what are we? We continue to communicate in some way pretty much every day. Fast forward to the fall and we decided to take a weekend trip together. Everything picks up where we left off in the summer and it was the best weekend. I chickened out asking what we are again but did embarrassingly sob when we said goodbye. We go back home and continue talking most days now we are going to another weekend trip together. So maybe I'll have an answer after this one. If I can get the balls to bring up what we are again. We know we like each other and are attracted to each other. But are we dating? Or am I so deeply entangled in a long distance situationship going nowhere? Help. I like you, you like me. Why aren't we dating? That boils it down.

[A]

Yeah.

[B]

This is every person in a situationship's plight. I like you, you like me.

[A]

Right.

[B]

We keep seeing each other, talk every day.

[A]

Yeah, this.

[B]

This is a.

[A]

Why wouldn't we be dating?

[B]

Right.

[A]

Right.

[B]

So are they dating? Jordana?

[A]

Unfortunately, they're not dating. But I wish they were.

[B]

We wish you the best.

[A]

I wish you. I wish they were because I see what she's like, how she's rationalizing this and like, she's definitely much. She's much more invested in this than he is.

[B]

Right. Right.

[A]

What do you think? Are they dating?

[B]

They are not dating. Here's the most important thing he's doing. He keeps all clear on the home front. Notice something in her email. She doesn't come to him even when they tried to go to him. Never can happen. The even their trips are away.

[A]

So they so romantic.

[B]

The one time she tried to go to his city, it was a no go. She ended up at my show.

[A]

Oh yeah.

[B]

She goes to my show in his city. Nothing happened.

[A]

Well, that was before they started hooking up. Right.

[B]

But again, it goes to the whole premise here where if it's in his home turf, he ain't messing that up. Okay, Home turf. He's. She's never had him.

[A]

He's at mom's beach house. It's fine. What happens at mom's beach house stays at mom's beach.

[B]

That's right. And he's got an out distance. Summer.

[A]

Let's see how it goes.

[B]

Right. They're running around like teenagers are sneaking around. Why are they sneaking around? Adults come over. Come meet my parents.

[A]

Yeah, that's true.

[B]

Right. They're dating in the alleys.

[A]

Yeah.

[B]

She's got mentioned this on a past episode. Main street dating. Alleyway dating. She is full alleyway cat. She's an alley cat.

[A]

Sorry. I get it. You're swept up in the room for a month. It was like hot and heavy. So I can see why you'd be like, all right, we're one of those people we like. We reconnected at our with the same. We both are rich, we have beach houses. We're meant to be together.

[B]

Right.

[A]

And then like, it is hot and.

[B]

Heavy and we like each other. He likes me enough to do all these trips.

[A]

Yeah. And we have a semi functioning romantic. I would call this a semi functioning romantic relationship.

[B]

Absolutely. And she's saying, I can't bring it up. And she knows it's because she tried.

[A]

To bring it up and it didn't go well.

[B]

She's the side door. She didn't even try.

[A]

Well, she's not bringing it up. Again, because she's not going to ask a question she doesn't want the answer to.

[B]

Right.

[A]

Because to ask the question. And then he says we're just so. He's going to give her the same answer. We're just so far. Let's just see how it goes. I'm having. I'm having a lot of fun. Let's just see how it goes. And she is also having a lot of fun. She keeps saying we having a lot of fun.

[B]

Right.

[A]

But she also feels horrible.

[B]

Well, she's like, I want a boyfriend for a weekend rather than no boyfriend at all. Because that's what she's getting with these trips. Like the trips are the real like heartbreaking part.

[A]

Well, that's the drug, right? Right. You're like, oh, I'm. I'll take like being confused and anxious in between the trips. Not knowing what we are for like these two days of I have a boyfriend and my. And everything's. And it's even better than when you have a real boyfriend because it's so amplified.

[B]

Right. Because it's like it is addiction behavior. Because like totally.

[A]

Yeah.

[B]

I'm gonna do two ways and two days of getting this heroin in totally bent.

[A]

I'm like a two day bender. And then I can. And then what am I going to give that up to have like things be like this.

[B]

Right.

[A]

Like totally just mediocre versus like really great and then really bad.

[B]

She'll deal with the hangover when it comes.

[A]

And that's what a situationship really is. If you break it down, it's like these really high highs that you don't really get from a normal healthy relationship because it's not as exciting to go on a trip with your boyfriend of a year that you know loves you and is gonna be and you're going home with.

[B]

Right.

[A]

This is like way more exciting.

[B]

And she might get the win. Maybe this is the trip that he says, let's move in. Let's be together. We'll do long distance. We'll figure it out. Kid.

[A]

Totally.

[B]

What should she do?

[A]

It's tough, but she. Okay. I think she should.

[B]

It's so hard to advise this because we both know she's not gonna do it or she's not gonna do it.

[A]

She's not gonna get what she wants. Let's start with maybe. I would say there's like a 2% chance that she gets that she leaves the situation with a boyfriend. But she's got to give up toxic to get good or great, hopefully. So I think she needs to do what you always suggest, she needs to do the reveal.

[B]

Right. She has to do, I think, a different form of the reveal. I think she has to, like, she's got to make him feel her loss.

[A]

Make him feel like shit a little bit.

[B]

Right.

[A]

How do we do it?

[B]

I think she's gotta say, hey, I can't go on this weekend trip.

[A]

Give it a consequence.

[B]

Right. I want to go on this weekend trip, but I can't because when we go on these trips, it makes me feel like we're together and I know that we're not. And then I leave here feeling like garbage.

[A]

That's a reveal.

[B]

That's a reveal. I feel like garbage after this trip because I had you as a boyfriend, and then I don't. And you got nothing but excuses, distance and beach houses and parents, basements or whatever the fuck. And you just say, I want to be with you. I want this to be a. I'm willing to do the hard part of having a long distance relationship. You got to. And I can't do trips with someone that I'm.

[A]

That's not my boyfriend at this point.

[B]

Right. You've tasted all the flavors you can taste at the ice cream shop.

[A]

Yeah.

[B]

And I think even if she wrote her sign off, I like you, you seem to like me. What? That's, that's a boyfriend to me.

[A]

Yeah.

[B]

And if you can't do that, I gotta go. I, I, it sucks.

[A]

Right?

[B]

I feel for her. I mean, it's the answer she wants.

[A]

It's hard to say there's a chance that could work.

[B]

There's always a chance.

[A]

There's a chance. There's a chance. But it's like, that's the, that's the only way it would work.

[B]

Right. And listen, you've, you've tried it. You've seen what it's like to be in a relationship with me. You either want that or you don't.

[A]

Right.

[B]

No more taste tests.

[A]

Yeah.

[B]

You know, not to compare her to, like, froyo.

[A]

No.

[B]

I was at a Froyo place in Boca last night. Free Trial is over, 700 flavors. I was behind her, and she wouldn't stop tasting. She's tasting this, she's tasting that.

[A]

How many do you think you're allowed?

[B]

How many tastes?

[A]

Two.

[B]

Three. At a maximum, three max. You get three. I will give you three. Three. I get it. And you have to choose one of the three.

[A]

Three's a lot. Three's a lot, I think.

[B]

Yeah, but you have to. One of those three. And you can't Just go, let me try the Chunky Monkey. Let me try the Rocky Road. Ah, let me try the Sherbert. And then you go strawberry. You can't go a four.

[A]

You must choose.

[B]

You getting an appetizer? Yeah.

[A]

All right.

[B]

This woman, she got.

[A]

I think she was classy.

[B]

What?

[A]

Two is classier.

[B]

Two is classy. Three piggish, but I'll allow it.

[A]

Okay.

[B]

Because I'll have three.

[A]

How many did she did? More than three?

[B]

I. It was like two hours. And I. My mom and I are behind her forever. My mom and I are behind her. We love Brandy's. And not all. If you're from the Florida area, Brendy's is amazing. But there's a thousand ice cream places called Brendy's that are not the same. Brendy's the one. There's good brandies and there's bad Brendy's.

[A]

Okay.

[B]

And we were at the good Brandy's, and this woman was in front of us. She's getting a milkshake, and then she's like, I'm going to try this and I'm going to try that. And my mom's, like, not easygoing.

[A]

Right.

[B]

To put it mildly.

[A]

Something.

[B]

My mom's going, what you get? What are we getting? You getting that? And then she. My mom's ordering ahead of her. I'll take this. And she's taking forever. She just says it. She says my mom will say things.

[A]

Like, look at her.

[B]

Yeah, of course. This is my life.

[A]

Are they fighting?

[B]

She, like, looked at her what?

[A]

Like giving her, like a. I don't.

[B]

Think people can believe it. Like, my mom's, like, talking about them as they're, like, within earshot.

[A]

Right.

[B]

She's taking forever. We'll have just orders. Good for her, good for her, bad for me. I mean, you have.

[A]

I'd be like, I'll see you in the car.

[B]

Yeah. I deal with this. I have to look at the woman. She's looking at me like, I'm going to talk to my mom.

[A]

You actually kind of like it, right?

[B]

Because you get something is comforting about it. You get my.

[A]

Yeah, you get your froyo. Faster.

[B]

I've never waited for froyo before. When I'm with her, I don't wait for much.

[A]

That's the life. Anyway.

[B]

Yeah.

[A]

This woman's a flavor at Brandy's.

[B]

She. Yeah, right. Three trials over three tries. He had the. He had the summer.

[A]

Yeah.

[B]

He's on try three.

[A]

He doesn't want to date her now. He's never going to Want to date her.

[B]

It's over.

[A]

He, He. I get it's hard. It's hard because she's having fun when she's there. She's loving it.

[B]

Well, she's being logical. She's going, we get along so well. Why won't we date?

[A]

Why wouldn't we be dating?

[B]

And he's probably fearful because women don't do that.

[A]

Women don't just, like, go on trips and hang out and, like, sleep with someone for a month. And I. I couldn't fathom being, like, into someone enough to do that, to go on a vacation with them, hook up with them, and be with them for all for a month straight and not want to date them. Like, for real.

[B]

I do. I can understand it.

[A]

Yeah.

[B]

Because, you know, with committing comes, okay, now I gotta move. I gotta find you a place. Like, there's, like, so much. He's emotional and it's weird. She's being logical and emotional, and he's being logical and emotional, but in two totally different ways. Cause she's like, look at, you know, like, we had the summer and will they, Won't they? But then she's being logical because she's like, we like each other, so why wouldn't we just date? We'll figure out the distance later.

[A]

Right?

[B]

And then he's being emotional. Cause he's like, I just don't want to be committed to the next step because I'm not sure if this will last forever. But he's being lobbyist.

[A]

She's not asking for that.

[B]

They're all asking for that. I mean, you're asking for the next step. Not immediately, but that the next step means the next step.

[A]

Right. Well, then hook up once and then move on. That's like.

[B]

Right, well, he. You gotta hook. You know, hooked on the. He liked that rocky road.

[A]

Well, why not find someone else to sleep with and hang out with?

[B]

Because it's not that easy. You just go, anyone. They have to. They gotta want to you.

[A]

I mean, this is.

[B]

This is. But I think, like, men, why do.

[A]

They want to have sex with you if they know that you don't. They feel that they know that you. That you are more interested in them. Like, don't they feel that? Doesn't that make them uncomfortable?

[B]

Yeah, that's what the reveal is supposed to do.

[A]

Right?

[B]

That's the whole point.

[A]

So why do they. Why do they still want to do it?

[B]

I think he isn't as clued in. He knows, but he's like.

[A]

He thinks she's having fun.

[B]

He's like she's going, she is having fun. She's saying she is.

[A]

Let's do fun.

[B]

Let's do another email.

[A]

Hey Jordana and Jared, all the softest feathers for your nuts and nether regions.

[B]

Thank you.

[A]

Huge fan of you both the pot and a new subscriber. I'm writing with a situation that is leaving me feeling confused. Cue the if you're confused, he's not interested adage.

[B]

Okay, no, that's not my.

[A]

That's not our adage. But I'm hoping you can shed some light.

[B]

If you're confused, you're turned off.

[A]

Change.

[B]

Huge views, perspective change.

[A]

I, 33, female, met a 40 year old guy at a Jewish event a few weeks ago. We really hit it off. Talked all night, stayed at the bar. Well, after the party ended, made out at the bar and so on.

[B]

Oh, Kanye is angry.

[A]

This goes against everything he stands for.

[B]

Really hates this Jewish love.

[A]

It was a super fun night and we had an incredible connection with endless commonalities and real things to talk about for hours on end.

[B]

Love it.

[A]

We exchanged numbers and texted back and.

[B]

Forth like matzo ball soup.

[A]

That's all Jews talk about. We just talk about matzo ball soup.

[B]

You went to summer camp.

[A]

We talk about loving matzo ball soup and hating Kanye West.

[B]

That's it.

[A]

Okay.

[B]

That's all we talk about, though.

[A]

We exchanged numbers and texted back and forth a bit over the following week with some light banter over text that both he and I equally initiated.

[B]

Okay.

[A]

We went out on a proper date a week and a half after our initial meeting. And the date was amazing. We had easy, real conversations, attraction, great chemistry and fun. I get it. It's great. I learned on the day.

[B]

Enough already with liking each other.

[A]

Give us the issues. Okay. I learned on the date that he's divorced. Green flag.

[B]

I didn't understand.

[A]

I didn't really see that. I guess he's not married. Great.

[B]

Big win.

[A]

It's a low bar. It's a low bar.

[B]

The guy who claimed to be single at the singles Jewish event wasn't married. Good. We did it.

[A]

This guy makes bad decisions.

[B]

Men are really good people.

[A]

Yeah. I learned on the date that he's divorced. Green flag. And that their marriage ended amicably after growing apart and different desires and having children. Green flag again. I wouldn't call that a green flag. I would call that fine.

[B]

Fine. Right? This is at least not a red flag. Sure. Right. Or I guess the green flag, if she's not saying, is that he wants kids and she wants kids. Maybe they're aligned.

[A]

I think it's also that. That it ended amicably. I think is everyone says that the.

[B]

Dump to someone else.

[A]

Right. That is always there, right? Yeah.

[B]

Amicable.

[A]

I have so much respect for them.

[B]

Right. That means you.

[A]

Yeah. If you respect someone after a breakup, that means you dumped them.

[B]

That's right.

[A]

He drove me home and asked when we could see each other again, saying it sounded like I had a busy weekend. I did. And when I said I could could make time, he suggested the following week instead. He needed to figure some things out.

[B]

He's gonna get rid of his wife.

[A]

I let him drive the texting conversation following our date on Wednesday evening. And we only exchanged a few text messages days after the date. No banter or attempts to make plans for the weekend. I hadn't heard from him since my last text to him on Saturday and then got this message Tuesday afternoon.

[B]

So they go on a date, no attempt to like banter over the weekend. And then they're supposed to have a date the following week. And he sends this.

[A]

Right.

[B]

Hey there. Hope all is good on your end. This week slash upcoming weekend is turning out to be a bit nutty. Could we pick it up next week? Say dinner on Wednesday night?

[A]

Okay. Our text exchange, or lack thereof following our date makes me feel like the amazing connection and interest I felt was actually one sided. Jj, what are your takes here? Am I being put on the back burner? This would put two full weeks in between our dates with minimal communication in between. And I feel that if he was actually interested, there would be more effort being put into communicating with me and scheduling the date. I'm trying to let this play out before jumping to conclusions, but would love to hear your thoughts here. Not a back burner batch.

[B]

I love this email. It's on theme with the subjects of the benefits episode as well as what we talked about in the beginning of this episode.

[A]

Awkward texting dynamic here.

[B]

Right? And to me, it's not as awkward like based on the facts.

[A]

Right.

[B]

You had a great date. I don't think. I don't think. Here's where I start at. You're not crazy. Okay, let me start it. You're not crazy. What you felt at the table at this date. I am sure that they are within reason of where you felt.

[A]

Sure.

[B]

I have to assume that. I just. I've been on too many of these things to feel like I. I've never been that far away. I don't think most people.

[A]

If you're making out at the bar the night you meet. I would assume there's a connection.

[B]

There's something there.

[A]

Sure.

[B]

It's also one date, so I think he doesn't have obligation to you. Okay, one date. And I'm not saying that's great. I'm not saying this is a good thing. I'm just saying it happens. I do think when you say I got all these things going on and you met a guy who's divorced and he's at Jewish events, I think this guy's dating. Like, I think you're not the only one he's dating. He might be having good dates with a lot of people right now, which is fine. But he is making the plan. His text to you is a thoughtful text.

[A]

He's trying to make the blood right.

[B]

He's. He said Wednesday night. He's giving you time. I know this isn't. It's a big deal, and it's annoying.

[A]

It's annoying because, like, there is a sense of. You're like, why can't I just get a guy who's like, we. I had this great connection. Why can't I just find a guy who also feels the same way and wants to see me as soon as possible? Because that's what she. How she was feeling. She was like, I was busy that week, but I said, I can figure it out. And he's like, no, don't figure it out for me. Like, we'll do the next week.

[B]

How old are they? Do we know?

[A]

I mean, he's divorced, so I assume he's in his 30s at least.

[B]

That's why, like, I. I think, like, a younger me is, like, jumping right in and, like, doing what you're saying.

[A]

Yeah, that's what we want.

[B]

Right. A younger me is a little less.

[A]

Like, let's. Let's keep the momentum. You talk about the momentum.

[B]

Like, let's. I think the momentum. I agree with all of this. I'm just saying, like, we're like, I'm thinking of myself and to be the vessel for this guy, especially as you get older, he's gone through a divorce. Like, how does, like, dating kind of change make people different over the years? I think you get jaded. And some of the jaded part is like, this is kind of like the other. Like, there's the jaded thing where it's like, you're kind of like, when are you gonna fuck me over?

[A]

Right.

[B]

And then there's the other side of jaded. And I kind of feel this is holding myself back to not someone over.

[A]

Okay.

[B]

You know? And I I think.

[A]

But both of those are bad, right?

[B]

They both suck.

[A]

Yeah.

[B]

I don't, I'm not proud of that. Like, you kind of lose your, your, your, your whimsy and wonder. Ww like you go.

[A]

Because you're not starry eyed and naive. Yeah.

[B]

Right. And also you've hurt people in the.

[A]

Past or you've been hurt in the case of the cynical.

[B]

Right. I'm saying as guy who may have hurt people.

[A]

Sure.

[B]

Who jumped in head first and was like literally like nuzzled in their arm as if we've been married for 30 years when we met like two days before.

[A]

Right.

[B]

I've done that and now I avoid that.

[A]

Right.

[B]

Like, and I go, well, maybe this makes sure that I go on all the dates so that I'm not disappointing anyone where I'm not really like. And it kind of sounds like what this guy's. He's kind of like stretching this out.

[A]

Right. It's almost like the last email with the guy who is with the Are we dating? Where the guy is going on vacation and has hooking up for a month and they're at their parents is like the other end of the spectrum. But then the person gets hurt and this one is like more distanced.

[B]

Right.

[A]

But the person gets hurt either way. She's still kind of like she's writing because she's hurt and probably not as deep of a way, but she's still like, why, like frustrated. I think that, I think if you ask most women, and again, this is. If you ask them, I don't know if they would respond this way after it was done. Would they rather you go all in and then decide you're not into it? I think so.

[B]

I can understand that. I mean, that also takes a lot of balls, you know, to like, to have done that in the past and feel how that feels. To like end something with someone that you're just like you've gone all in with.

[A]

Right.

[B]

I just don't want to do that. It could be fun, but it's like I don't even want to do that again. Like, I, Yeah. I'm saying they're putting a lot of my own experience under this guy.

[A]

Right.

[B]

My. I guess the, the part that, you know, we have, we can deal with the emailer, you know, her plight of like, it's okay to be turned off. She's like, she wrote confused in the beginning. That whole attitude we didn't give.

[A]

You're gonna call it turn off. Yeah.

[B]

It's okay to be like, I'm a little Turned off by this. But we'll see what happens Wednesday, right?

[A]

I think she should still go. I think she gave another. I think someone is allowed one reschedule with an. If they're. If they're offering another date.

[B]

I would also say to her, like, let's go in with, like, a kind of a plan. If I. If I'm to, like, ease or, like, anxieties. If I were her, my plan would be, let's see what happens Wednesday. Let's see if we have the same magic that we had the first time. And then I'm going to invite him to something that I'm doing that weekend with friends.

[A]

Okay. So she's gonna initiate the momentum.

[B]

I think that that places a momentum on things that actually, like. Cause I'm thinking of, like, how, you know, how would I fight me, you know? And I'm like. I think the thing he's fearing is that, like, you know, what she wants is, like, first date, second date. Now we're just like, it's winter and we're hanging out every day.

[A]

How did we wind up here?

[B]

Right? Oh, my God. Three weeks we've gone, we've have them separated. And I do understand wanting that. I do think as I get older, I shy away. I'd rather be alone than. So I think, like, encouraging a hang that is, like, almost like, because you're trying to meet a friend. Like, I think about that a lot with my dating life. It's like, you see, like, these couples at work, they all say that they're friends, and I'm like, I can't imagine making a friend at 39 years old. Like, I actually can't. Like, at this point in life, I'm like, I avoid all maybe friendships everywhere.

[A]

Yeah. Your next friend is gonna be your wife.

[B]

That's what I'm saying.

[A]

Yeah.

[B]

And it's like. But I haven't made a friend in, like, a decade.

[A]

Same.

[B]

So it's like, who am I to say I'm gonna make this friend at 39, 40. Now that when this comes up, 40, I'm fucking old. But I'm saying it is actually crazy to me to think that I would make a friend at 40.

[A]

Right?

[B]

Because I am looking for. You see these dating apps?

[A]

Looking for my best friend.

[B]

Look for my best friend. And I'm like, okay, it's a little late for that. We didn't grow up on the same street.

[A]

You are looking for your best friend.

[B]

Right? And I agree with the statement. I think it's insane to try and, like, put into Practice based on the way we're doing it with this, like, again, this guy. She's like, look at all these connections. We, like, know each other without knowing each other. And now they haven't even gone on the second date yet.

[A]

Right.

[B]

So, like, I'm sure from his angle and vis a vis my angle, I would be like, easy there. I got friends. So I think if I'm to give her a plan, this is like, me.

[A]

All right, give her the plan. Give her the plan.

[B]

The plan is you go on this Wednesday date, let's see how it goes. Let's see if you're turned on. Let's see if you have fully recovered. And then I would present, like, kind of a low pressure option.

[A]

Okay.

[B]

Of like, that you would do with a friend.

[A]

Give me an example.

[B]

Hey, I'm going.

[A]

The date goes well.

[B]

Second date goes well. I have this. I have a friend and I are going to the local farmer's market. This isn't very good season wise, but, like, we're, you know, the local. You want to come hang with us? We're going to get, like, coffee and, like, have these, like, really good, you know, pastries that are out at the. Do you want sober?

[A]

Sober.

[B]

Sober. You have the friend there. So now you're on a Main street hang. This is the alleyway hang. This is like. And I'm going with a friend. You're more than welcome to meet up and hang, like. And I think that's like one of those, like, I'm just putting out the milk to see if he'll drink it.

[A]

Right. And what if he's like, I can't. Busy.

[B]

What are you doing this weekend? What's your other plans? And then who are you seeing? Yeah, I thought we were exclusive. Well, I just, like, I think you move on from it. But it's like, it's kind of telling.

[A]

You, like, he's not going to be into the momentum. Yeah, right. And would you go do you had two great times?

[B]

I really had a good. Yeah, I think I would. I think I would be more likely to go to the farmer's market. I like a farmer's market. You don't like.

[A]

I do. I do. I like a farm. I can.

[B]

I like it.

[A]

You do. Okay.

[B]

That's good. I like a farmer's market because I like to, like, judge all the things.

[A]

Okay.

[B]

And like, you know, I go to the.

[A]

It's kind of nice. Yeah. You. I went to in Williamsburg. They would have them a lot.

[B]

They have them there. But, like, even every city I go to there's always something like that on a Saturday. There's always like just a bunch of people selling their popcorn.

[A]

Yeah.

[B]

And then I like, you know, you buy stuff. I buy some things.

[A]

Artisanal pickles.

[B]

I love pickles.

[A]

Same big fan of pickles.

[B]

Do you like sour pickles or sour? You do.

[A]

Mike likes half sour. I like sour.

[B]

I'm a half sour guy. I like a pickle to be more like a cucumber than a pickle.

[A]

Really?

[B]

Yeah.

[A]

Now I'm the other direction.

[B]

Really?

[A]

Yeah. But he's with you. So we have, we have all in my.

[B]

If you ever come over, that's a good pickle match. Because you go to like a deli and they put out the pickles. They always give you the different shades.

[A]

Yes. Also same with wings. He doesn't like the drumstick, so I get all I do.

[B]

You're a drumstick.

[A]

I like the drumstick. Yes. So he likes. That's the one of the few things he'll share with me.

[B]

I'm bisexual. Wing wise.

[A]

You'll go either way.

[B]

I'll eat all the way.

[A]

Okay.

[B]

Yeah. I think there's different types for different moments. I don't like a drum. That's too big.

[A]

I would agree. Smaller is smaller is better.

[B]

I want like skin to meet.

[A]

You want to work for it?

[B]

Yeah, I do. But I, I, I know this is a tough answer for her. Like to like have a plan waiting in your back pocket that is a little more casual. It's a little Three Bears ish. You know, not too hot too, not too cold. Just right. I, I, but I'm, I, I hope the sentiment comes through.

[A]

Is there a chance this guy, like really dates her for real?

[B]

Yes, absolutely. I'd say the chances are like, we still don't know. This could be a real relationship.

[A]

Got married. You know he can commit.

[B]

Right.

[A]

It's within his capacity.

[B]

I don't think we're hearing you got divorced.

[A]

So you know he can dump someone too.

[B]

Right. He's good at that. And he's got a good branding amicable. But I just don't know. I think he's dating other people. I think like you met him at a bar and you're kind of like a wild card. Like he probably has like a bunch of dates set up from a dating app. This guy's on a dating app? Probably he's got a couple dates set up.

[A]

Don't men have, like, enjoy an in person interaction more also?

[B]

I think we all do. But I think, you know, you like a woman With a rotation.

[A]

A woman would give up a dating app date for a good. A good in person interaction date.

[B]

I think most people would, but I think you just plan shit. You just. You have plans on the calendar.

[A]

Okay.

[B]

I mean, like, I'm in that game right now. Like, I. I'm on hinge.

[A]

And have you ever met someone where you're like, I'm gonna cancel my dates for the week. Just focus on this person.

[B]

I have. The thought runs through my brain, but.

[A]

You don't do it.

[B]

It's hard.

[A]

Okay.

[B]

It's hard. It's a little bit. I mean, that's gonna be bad for people to hear, but it's like. But what if, you know, like, you get caught up in that, right? It's hard.

[A]

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[B]

All right, let's play some games.

[A]

Good luck. Let's play some games.

[B]

We love Red Flag. Deal breaker. If you don't know the game listeners write in they're having a perfect date. This one thing happens. Is it a red flag? You see it and you just like, keep going or it's a deal breaker and you're done?

[A]

Uupetches.com keep sending them in.

[B]

J and J. Longtime listener, first time writer, huge fan of you both. I saw Jared in Montreal, had the best time. Thank you. That Montreal show.

[A]

You had a great time.

[B]

What a town. I have a red flag or deal breaker about dating app conversations. I've been messaging this one guy on a dating app and cannot always reply right away, obviously, which is usually nothing to note. After I didn't respond for a few hours, he responded with question mark, question mark, question mark, question mark.

[A]

That is so aggressive.

[B]

That's a lot of question marks. And then. And she's gone. Oh, this guy.

[A]

And she's gone.

[B]

So annoying.

[A]

You're the narrator here.

[B]

I know. And it is so you said it exactly how he said it.

[A]

Yeah.

[B]

This has happened with other men I've chatted with on the apps too. I've had even had one guy say, are we gonna get to know each other or not? Well, for me, this is pretty much a deal breaker and I usually unmatch. I am not sure if this is too much of a leap, but to me these feel like warning signs that a guy could be possessive or doesn't respect my time. These are sort of fears that make a it a deal breaker since double texts are annoying on their own but not really a huge deal. To be clear, I'm not saying double texts are a deal breaker, but rather when a man questions why I haven't replied yet, even if it hasn't been that long. So what do you think? Red flag or deal breaker? What do you think?

[A]

I think on a dating app those kinds of responses would be deal breakers. I do think if you're like, have met someone and you've established something. I also still think those are aggressive, like, and she's gone. Or like that's like an annoying way to immature kind of way to get a response.

[B]

Right. It doesn't even like acknowledge that they have a life of their own and Right. Have things going on.

[A]

Especially on a dating app when someone owes you. We've said this all the time. Nothing.

[B]

Right. They're making something personal that isn't personal at all.

[A]

Totally. If the only situation where it's acceptable to ask someone where the hell they are is you. You went on the first date, the second date is coming up. You're trying to book a place. It's time sensitive. They didn't answer. And then you could follow up and say, hey, I'm really sorry to be like bothering you. I'm sure you're busy. I really just need to know.

[B]

That's the problem with their text. It's like putting it all on her.

[A]

Four question marks. Get a life.

[B]

Right.

[A]

If you used to, you know, now you can do the. The reaction question mark.

[B]

Yes. Reaction question mark is. Yeah, that's aggressive. I will say this, that I do think her saying it's like a possessive thing. I disagree. I think it's a self conscious thing. I think they're taking out their anger with the apps on you.

[A]

Right.

[B]

I think they got ahead of themselves and they kind of emotionally masturbated to the idea of like they're attracted to you and they think you're a catch and they've mastered you on the app.

[A]

And now do they know that that help?

[B]

I think they're just trying to like, you know, I, I think that to me, this is when someone, she's getting this multiple times. I'm sure these guys are like, see something.

[A]

Yeah.

[B]

And they're like. And I've had this happen to me. I have people do that to me. Oh. You know, they'll respond, you know, but it's a little bit nicer from a woman. I think a lot of times the women will be like, I'm gonna try this again. I didn't hear from you. Back from last.

[A]

We are less like ego driven, I think. Yeah.

[B]

It definitely has to do with it. So I, I don't think this comes from a good place.

[A]

Yeah.

[B]

So I would, it would be a deal breaker for me.

[A]

Right. It would just be like this person's like taking it to the next level, like so quickly. Right.

[B]

You've taken something very personal that like this is supposed to be fun. Like we haven't even met yet. Like, I have no investment.

[A]

You're already fighting with me.

[B]

Right.

[A]

Yeah. That's what I'm saying. It would be different if you've already been out. I still don't think these are the way to do it. But you can ask someone. Like, sometimes I'm not sure if you're interested in me. You feel like you, like, don't really answer that much.

[B]

Totally different. Yeah. Yeah. I mean, like I've written back, are we alive today? Like to someone I've met, not to someone I've never met?

[A]

That's what I'm saying.

[B]

Yeah.

[A]

Like there's a. There's a context to it. These people don't have that. All right. When I was 21, I had just gotten out of a long term relationship. On my first single night out on the town, I met a man while out with my friends. For the sake of my story, let's call him Simon. I'm really attracted to him and he has a super weird, mysterious essence to him that I still can't quite explain.

[B]

Simon, the mysterious.

[A]

I was gonna say, sounds like he's married. We hook up that night and for the next few months, we sporadically meet up and hook up. I finally asked to see him ahead of time rather than our usual late night meetup. So we start going on dates. This begins our next chapter.

[B]

So dramatic.

[A]

He takes me on super nice dates at a caliber I had never experienced. Sports games, nice dinners, etc.

[B]

I thought the Simon.

[A]

Right? I thought maybe we were going to date. It seemed like he wanted to. Eventually he moved to another city and got back together with one of his exes. Okay, I guess.

[B]

Not one of them.

[A]

Two years later he moved back to the same city as me and I got a text from him asking to see me. After weighing the pros and cons telling him no, but then circling back and saying yes, I see him. It feels exactly the same as before, but better. We start to go on fun dates again for a few months. He tells me he is sorry that he missed me, that he has changed, and that he regrets going back to his ex instead of being with me. One night after returning to his place for the evening, I see that there is a pot next to his bed on the floor by the side table. The kind you would use to boil pasta, I say. What's up with the pot? I ask, laughing. Oh, he says and pauses. Well, that's for when I have to pee in the middle of the night. If I walk to the bathroom, it wakes me up. You know, once your body starts moving, it wakes your brain up. And then I can't fall back asleep, so I just piss in this so I don't have to get up. He said it matter of factly, like it was normal. Smart even. I stare at him, puzzled. Oh really? Okay, I truly did not know what to say.

[B]

You don't have a piss pot.

[A]

It's all the rage. You've seen me do this before, right? No, he most certainly had not. He probably was mixing me up with another girl. He was seeing someone he had already hit the piss pot stage with one.

[B]

Of the other piss pot ladies.

[A]

I don't really say anything. I just sort of nod and look away. Well, I'm glad you don't think it's gross, he says. Of course I think it's gross. I wake up not once, but twice to him hunched over the side of the bed, naked, in the middle of the night, tinkling in a pot.

[B]

Look away.

[A]

Nothing looks more attractive in my brain. Thinking this in the morning, while I'm going to make his coffee, he brings his little piss pot. He dumps the piss in the kitchen sink and the pot is just sitting there while he makes coffee. This is so gross. I left and that was the last time I ever did or ever will see Simon. So red flagger, deal breaker. He keeps a pot next to his bed to pee at night.

[B]

We didn't really need the whole question.

[A]

A couple of paragraphs.

[B]

Yeah, about how wonderful and everything Right.

[A]

He left and came back.

[B]

But he was Christian Grey right in the beginning. No one touches me. Like Simon.

[A]

Yeah. This is disgusting.

[B]

He has a piss pot next to his bed. Yeah, it doesn't really go with the story.

[A]

Here's the thing. I do, I agree that when you get up in the middle of the night to go to the bathroom, it does, you know, get you out of the groove of your sleep. It's a decision you have to make when you, like, if you do wake up, like, is it worth moving my body?

[B]

Right.

[A]

That part of the statement, fine, to do it with someone that you, to do this as a solution is crazy. No, this is also to do it with someone you're like, I can understand not wanting to do that on a nightly basis. If I live alone, maybe. Yeah, the sink part with the pot is disgusting. It, so that's the deal breaker in itself. But, like, even if that's your thing, even if that's your, like, clever solution, to do it with someone that you're newly sleeping with would be so crazy to me, you don't even care.

[B]

This is how I live. Deal with it.

[A]

Gross.

[B]

Hey, good morning, honey. Yeah, I'm just going to pour out the piss pot and then we can go. Yeah.

[A]

What if a woman did this, it.

[B]

Would be quite a feat to watch her get the squat. Yeah, I, I, I have to say, I've seen, you know.

[A]

Or you'd be out.

[B]

I'd be out, Yeah.

[A]

I mean, you're kind of into it. I just, she's an animal.

[B]

An animal. Just the weirdness. It's just like, if a woman did this, I'd be like, I need to know more as much as possible before I leave here.

[A]

Right.

[B]

But no, I mean, like, I can't even imagine a woman doing such a thing.

[A]

It's disgusting.

[B]

Right?

[A]

We would never. Because we're not disgusting.

[B]

I, I, it is very male, this, like, well, you have to pee. So put the pot next to the bed. Like, it's like very like, I can fix this problem. No, real quick. I'll just put a little cylinder next to the bed. I'll lean over, I'll put my penis in the cylinder and of course, go all the way. I have a series of.

[A]

Your penis in the cylinder.

[B]

Yeah. I have a series of tubes that lead it right to the toilet and we're good to go. So it's just bizarre. Okay, let's do one more. J and J, longtime listener, new benefit subscriber. Thank you so much for all the dating advice through all these years. Your insight into advice has got me through a four year long situationship where I finally learned to create my own closure and end it for good. Falling in love again and being in my first healthy relationship. And now, unfortunately, getting through my first adult breakup slash hard break. We've gone through the whole series of things we have. I'm slowly getting back out there again and came across this hinge prompt attached below. Personally, I do eat meat socially, but I prefer to eat vegetarian at home. I'm very open to dating someone with different eating preferences than me, but this response really turned me off. Curious what your thoughts are. Thanks for everything. Okay, so here's the prompt. You should leave a comment if you're not a vegetarian. Clenched teeth emojis can hit a tennis ball. Prefer to eat family style and want to grab a drink slash coffee.

[A]

To me, this is why context and the receipts are so important. This wasn't that bad when I saw it. When she, when she shows the actual display.

[B]

Right. It's a little softer with all the.

[A]

Other things, it's a little more playful. This guy's just telling you he loves eating meat, he loves to play tennis, he, he likes family style and, and getting coffee.

[B]

He's definitely made a judgment on vegetarians. Like, that they can't even be like, dealt with like, that. They're like too much of a pain in the ass to even date.

[A]

Right. I read it a little more jokey.

[B]

But I read a joke. I agree with the emailer.

[A]

Okay.

[B]

The idea that like really like, is that how you look at the world, that like, you could never like, I've seen this from the male side too.

[A]

Right.

[B]

You should not go out with me if you're a vegetarian. Like I've seen that.

[A]

I think maybe he like really does not think he would be compatible with a vegetable. With a vegetarian. You wouldn't date someone who wouldn't eat Chinese food on a Sunday night.

[B]

Absolutely. That may be the case. I think living an I phrases is better than you phrases. So, like, I think this is off putting just because it's a you phrase.

[A]

You don't like this prompt?

[B]

I don't like the prompt.

[A]

I guess the prompt is you should leave a comment. But he's made it negative.

[B]

Yeah, he's made it negative. I think you have to be. I, I think any prompt response should be personal, light and vulnerable.

[A]

Okay.

[B]

And this is not personal. This is not light.

[A]

So you'd prefer you should leave a comment if you love meat.

[B]

Right. You love going out for barbecue. You. Yeah, like, wouldn't that be a great thing?

[A]

That's a better, more positive way to do it.

[B]

Isn't that a more fun person to talk to? Like, what are we gonna do? Like, on vegetarians for our first conversation, I guess, right. Like, I could meet an annoying omnivore or carnivore or whatever and an annoying vegetarian. Like, I, I, I think.

[A]

Right. I agree with you. That's, that's fair. It would be a red flag for me, but I agree it would be better if he phrased it more positively.

[B]

Right. If this person's like, again, to go back to the beginning of the show. Like, if they're hot, but we'll push through and see what happens. Like, if I find them, like, if I'm attracted.

[A]

Right.

[B]

If I'm more.

[A]

It wouldn't be a deal. It wouldn't be a deal breaker.

[B]

Not a deal breaker. But it also, to me, I think, you know, if we're to, like, play the percentages game, the person who writes this in their profile, probably not a fun hang. I don't think they're, like, as cool as they think they are. I don't think they're as fun as they think they are.

[A]

Just gnawing their ribs.

[B]

Yeah. Like, I don't think they're good conversation. Right. We're going to sit there, suck on ribs.

[A]

Yeah. No, I agree. And there's a more fun way to say all of those things.

[B]

You've chosen negativity over positivity.

[A]

Right. So you stink. But I'll, I agree. Just a red flag.

[B]

Red flag. Well, we solved dating again.

[A]

We did it. We'll be back next week.

[B]

Boom.

[A]

We'll be back on Friday.

[B]

Friday. Feeling Friday feels boom.

[A]

Bye. Kate McAuliffe is our senior producer. Our editor is Emily Freedom. Candace Menega is our senior social producer. Our associate producer is Will Maxwell. Additional production help from Shannon Jimenez Sason. Be sure to follow us at U Up podcast and send us your emails to uupetches.com Olivia loves a challenge.

[B]

It's why she lifts heavy weights and likes complicated recipes. But for booking her trip to Paris, Olivia chose the easy way. With Expedia, she bundled her flight with a hotel to save more. Of course, she still climbed all 674 steps to the top of the Eiffel Tower. You were made to take the easy route. We were made to easily package your trip. Expedia made to travel flight inclusive packages are atoll protected betches.