Should You DM the Girlfriend If You’re the Other Woman?

Summary

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Episode Overview

Podcast: U Up?
Episode: Should You DM the Girlfriend If You’re the Other Woman?
Hosts: Jordana Abraham & Jared Freid
Date: April 24, 2026

In this lively episode, Jordana and Jared dive into one of the most controversial gray areas in modern dating: what to do if you discover you’re the “other woman,” and whether you should reach out to the girlfriend. The hosts discuss listener emails, bringing their signature honesty and humor to questions about dating app frustrations, revenge versus good intentions, the etiquette of outing cheaters, and the transactional feelings around dating as an adult.

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Key Discussion Points & Insights

1. Catch-Up Banter: Travel Woes, Drinks, and Service (00:33–14:56)

• Airline & Delta Talk: Jared recounts a recent travel experience, including an inside joke about seat 11A, plane crash statistics, and airline staff. Both hosts riff on airline personas and seating stratagems—Jordana jokes about booking aisle and window as a couple to avoid the middle (“No one wants to sit in between a couple” – Jordana, 06:37). Jared calls himself “the wrist in this scenario” (08:37) when taking one for the team on cramped flights.
• Client Dinner Recap: The hosts attended a client dinner together, praising the impeccable, “Plaza Hotel-level” service at a restaurant called Masara (13:03).
• Quick Plug: Jared announces dates for his comedy tour and new book, “Walking Red Flag.”

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2. Main Email: Should You Tell the Girlfriend? (17:56–29:46)

Email Summary (From 17:59):

A listener explains she unknowingly dated a guy who had a girlfriend during college (2018), discovered the truth via social media, and after confronting him (“When I asked if he had a girlfriend, he just replied, ‘What?’” – 19:18) messaged the girlfriend on Instagram. The message went unread, so she unsent it, later feeling unsettled and guilty.

Hosts' Analysis and Debate

• Petty or Prudent?

  • Jordana: “I think in college, especially when everyone’s in the same bubble, it’s more important to tell people… It just seems less weird in college” (21:01).
  • Jared: Contrasts, suggesting it’s a prudent move at any age, but more justified as an adult for the sake of other parties knowing the truth (21:37).

• Lingering Guilt & Revenge Motive

  • “She has to admit that part of the messaging [the girlfriend] is a little bit like revenge against this guy for not even having like the respect to articulate a real response” – Jordana (24:45).
  • Jared is surprised the emailer is still fixated on an event from eight years ago, highlighting gender differences in processing dating history: “Men just go, ‘win some, lose some’… This is where we differ” (25:44).

• The Role of Closure

  • Jordana: “Fear no woman… Like a woman who doesn’t have closure” (25:06).

• Advice Moving Forward

  • Both agree the girlfriend probably read and dealt with the message quietly: “No one misses that message unless they have 6 million followers… She handled it in the way she wanted to handle it” – Jared (26:42).
  • “Petty would be to go back and remess[age] eight years later… That would be crazy” (27:34).
  • The hosts warn against trying to force closure or reopening old wounds years later.

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3. Second Email: Dating Burnout & App Exhaustion (30:45–47:57)

Email Summary (From 30:51):

A single 32-year-old man details his recent dating life in a Midwestern city, quantifying first dates by profession, age, cost, tipping amount, and outcome. After multiple unsuccessful first dates, he’s frustrated by what feels like “one-hour evaluations” and questions what women his age are looking for, speculating if he’s “too friendly” or if women “avoid settling.”

Hosts' Reaction

• Data-driven Approach & Transactional Energy

  • Jordana points out that tracking exact spending and outcomes signals a transactional, “spreadsheet” mentality that women can sense:

    “If he's bringing that energy to a date… people can sense that, that there's like he's bringing a level of transaction to the state so they're feeling transactional.” – Jordana (38:55)

  • Jared jokes about the “bullet-point” style and says when the process gets this analytical, it’s a sign to take a break from apps (40:45).

• Advice for Burnout

  • “Delete the apps… We all have that time. I've been there, Jordana, you've been there.” – Jared (41:17)
  • Recommends focusing on platonic friendships, group socials, and real-life connections to reset attitude and regain natural social confidence:

    “He needs to plan a hangout with friends… Get back to his roots… Do a barbecue, get a win here.” – Jared (45:11 & 45:32)

• Unresolved Issues from Past Relationship

  • Jordana insightfully notes the man’s fixation on money and relationship “outcomes” is probably lingering resentment from losing money on a cohabitation split:

    “Maybe that's some left over from his ex… process this breakup a little bit more.” (45:45)

• Telling Signs You Need a Dating Detox

  • Jared's list of "delete the app" red flags:
    • Tallying losses/expenses as proof of resentment (42:01)
    • Claiming, “the app isn’t showing me the good ones” or blaming the algorithm (43:12)
    • Talking about “wasting time,” as if forced into dates (43:54)
    • Describing people as “low effort/quality” (44:11)

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Notable Quotes & Memorable Moments

• On Airline Couples:
  “You don’t love each other enough to sit with each other, so you risked it. Now you get me in the middle of your relationship. I’m your throuple.” – Jared Freid, 06:53

• On Telling the Girlfriend:
  “She replied ‘what?’ That’s very college.” – Jordana Abraham, 24:24
  “Petty would be to go back and remess[age]… eight years ago… That would be crazy.” – Jared Freid, 27:34

• On Transactional Dates:
  “No, not everyone has to... Just a good tipper does not always get [the date]… That’s what my grandma always said.” – Jared Freid, 42:51
  “If he's bringing that energy to a date… people can sense that, that there's like he's bringing a level of transaction.” – Jordana Abraham, 38:55

• On Dating Burnout:
  “When you start tallying your losses, like this guy, delete the app time.” – Jared Freid, 42:01
  “He needs to plan a hangout with friends… Do a barbecue, get a win here.” – Jared Freid, 45:31

• On Lingering Breakup Issues:
  “Maybe that’s some leftover from his ex… process this breakup a little bit more.” – Jordana Abraham, 45:45

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Important Segment Timestamps

• 00:33–14:56 | Catch-up banter: airline experiences, client dinner, New York stories
• 17:56–29:46 | Main email: Should you DM the girlfriend if you’re the other woman? (analysis, intentions, closure, advice)
• 30:45–47:57 | Second email: Dating burnout, spending, and dating-app “exhaustion” (detailed breakdown, hosts’ guidance)
• 43:12–44:59 | Jared’s “Delete the App” warning signs

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Episode Takeaways

• When you’re the “other woman,” messaging the girlfriend is more about your intentions than her, and closure can be elusive. Once you’ve done your part, move forward—don’t dwell or reopen old wounds.
• If dating feels like a miserable transaction, that attitude will show; take breaks to refresh perspective, focus on positive relationships, and avoid itemizing “losses” as proof that dating is broken.
• Whether confronting a cheater or enduring date after date, honesty with yourself (about your motives and energy) is key to healthy modern dating.

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Hosts’ signatures: Blunt honesty, pop-culture references, and big laughs—turning even dating disasters into learning moments and relatable comedy.

Transcript

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[Jordana Abraham]

Welcome back to the UF podcast. I'm Jordana Abraham.

[Jared Freid]

And I am Jared Freed. How you feeling on a Friday?

[Jordana Abraham]

I had two drinks last. I had two aperol spritzes and apparel spritzes are almost like. I feel like not even real drinks. They feel like a half a drink.

[Jared Freid]

So, like, it's, it's almost like. I would compare the aperol. I would say the aperol spritz, flavor wise, is like the adult Shirley Temple.

[Jordana Abraham]

Yeah.

[Jared Freid]

Like, it's not, it's not sweet like a Shirley Temple, but it has all the elements of Shirley. Some would say the adult Shirley Temple is an adult. Is, is a vodka and a Shirley Temple.

[Jordana Abraham]

Dirty Shirley. Dirty Shirley, as they call it these days. Yes.

[Jared Freid]

Yeah. Which Dirty Shirley? Great name. I, I would, if my name were Shirley, I'd go by Dirty Shirley.

[Jordana Abraham]

That would be great. If you were a woman, a certain kind of woman. For sure. Yeah. So I had two aperol spritzes and I wasn't even like, remotely anywhere near drunk, probably, but I fell asleep and then I woke up to you.

[Jared Freid]

I don't know. I was, I was having some ch. Chitchats. No, I'm kidding. You were great. Yeah, I guess, I guess. I see you know how drunk you are. You didn't even know how drunk you you were.

[Jordana Abraham]

No, I was, I think I was fine.

[Jared Freid]

No, I'm with you. I didn't even know you were drinking to be. I just thought you were maybe having like a dirty shirt.

[Jordana Abraham]

Shirley Temple. Yeah, that would be weird. No. But then, you know, I went home and I fell asleep immediately. And then I got. And then what? I. That this happens to me because I haven't really drank in a bit due to being pregnant and everything, but I like, woke up at 3:30am and you're just kind of like up the whole night. Like, it really messes up your sleep. It's very. I was like, that was so not worth it. I didn't even feel, I didn't even feel a buzz from that. And I'm paying for it for no reason.

[Jared Freid]

It is the worst. I, I, I get it. Listen, I especially, you know, last night to let the people behind the Curtain. We had like a. Would you call it a client dinner?

[Jordana Abraham]

Yes.

[Jared Freid]

And you know. A dinner. Yeah, Client dinner. I, I don't go to many of these. I don't get. They don't let me out. The baches don't let me into there.

[Jordana Abraham]

Well, they need.

[Jared Freid]

There are certain times their business affairs, but then they got to bring in the big gun. Yeah. The fourth founder.

[Jordana Abraham]

Yes.

[Jared Freid]

Held at bay.

[Jordana Abraham]

Yeah. So we went to, we went to that. It was like a client dinner. And that's why we saw each other and that's why you were in town.

[Jared Freid]

Well, to add on to the client dinner, one of the clients was from our good friends at Delta who we would love to do some work with.

[Sponsor/Ad Voice]

Yes.

[Jordana Abraham]

You know, you're listening.

[Jared Freid]

Go to Plug City for them. Yeah, here's some. Here's a little taste. Here's a little free taste of what you could hear from us. But there was a woman there from Delta and she was saying that she was great conversationalist. She was like, you know, the only seat that, you know, every. Every plane crash, there's one seat that lives. Oh, do you remember that conversation?

[Jordana Abraham]

I thought it was one seat that dies. It was one seat that lives.

[Jared Freid]

No one see that lives. 11A. She's like, 11A lives no matter what. Airplane crash.

[Jordana Abraham]

Okay.

[Jared Freid]

You know, and I was like, well, thanks. I'm flying tomorrow. This is a fun dinner time conversation.

[Jordana Abraham]

That's very funny because I was kind of like half overhearing the conversation and I kept hearing 11, 8. And I thought she was saying that 11A dies. So I thought the joke was like the opposite.

[Jared Freid]

No, no, no, no. It was, that's where you gotta be. But you know, just. And then the conversation turned to plane crashers. And I'm flying at 7 in the morning. And so I woke up 5:15. I. I go to the airport. The. I look at the, you know, the seating chart completely full. And like I'm in coach middle seat. I haven't been in a coach middle seat.

[Jordana Abraham]

Embarrassing in.

[Jared Freid]

Since I've been a baby with my parents. That's like, it's crazy.

[Jordana Abraham]

That's your version of a twin bed, right?

[Jared Freid]

Yes, yes, the reference. Last episode. That is. I, I was like, I can't have this. But it was a full flight. But I saw that the last row was open. You know, they, they like block off the last row. I'd rather have last row aisle than row 19, middle seat.

[Jordana Abraham]

Yeah, I think I agree with that. Even though it's a little. It could be a little smelly. Back there. Sometimes it's tough.

[Jared Freid]

Smell is. I'm smelly. I don't give a. I don't wanna, I don't want to be, like, in between two coach passengers that don't even get upgraded. Disgusting. So I was like, instead of going in the lounge to get my coffee, as I do, I went straight to the gate and I, you know, the West Palm to New York, New York to West Palm, West Palm to New York flight. It's a real show. You're getting the. I think the toughest customers in the game are going LaGuardia to West Palm. Like, there's.

[Jordana Abraham]

That's where I'm going, people that next Sunday.

[Jared Freid]

Yeah, you're gonna be amongst. It's. It's like everyone on that flight would have their table moved immediately if they were sad.

[Jordana Abraham]

Oh, okay.

[Jared Freid]

Like, everyone has that energy. And, and I've hear from flight attendants in the past where they're like, yeah, the, that, that route, we kind of have to, like, really just be, you know, aware.

[Jordana Abraham]

I have a flight etiquette question for you.

[Jared Freid]

Okay, go ahead.

[Jordana Abraham]

Do you think, and I mean, you haven't done this because you haven't really been in a relationship in a while, but now that you're in a relationship, do you think it's like an. Move or strategic to book if you're a couple? Window, aisle, hope no one takes the middle.

[Jared Freid]

I think if you're a couple, I think going, the problem is if you're in a couple where you're like, I'm a window and they're an aisle, you know, and you're like, that's. I'm not gonna bend.

[Jordana Abraham]

Right. But no one wants to sit in between a couple.

[Jared Freid]

Right? No, I, I, I'm, I've, I've been in between the couple. I've had that where they're, like, reaching over me and starting the movie at the same time. I'm like, hey, that goes.

[Jordana Abraham]

Let's switch.

[Jared Freid]

You lose that privilege when you guys stop sitting with each other. You don't love each other enough to sit with each other, so you risked it.

[Jordana Abraham]

Yeah.

[Jared Freid]

Now you get me in the middle of your relationship. I'm your throuple. Yeah, yeah. No, I think it's, I think it's rude. I think it's good to book those fights.

[Jordana Abraham]

Okay.

[Jared Freid]

I, I mean, I booked it, and I go middle. Middle window or middle.

[Jordana Abraham]

Who's in the middle?

[Jared Freid]

You know, we've. She takes middle, but I'm like, jump on this shoulder. You get, you get all that show. Well, that's my big show.

[Jordana Abraham]

You have, you have to say, like, if you're going to take the window, you have to allow the other to like, you have to be the human armrest.

[Jared Freid]

Yeah. I think it makes it a bigger seat for both of you when you put up the armrest and you kind of like share that middle area that, you know, because you can touch comfortably. That opens up like four inches.

[Jordana Abraham]

Right. Well, what I do is I book the middle. I mean, sorry, I booked the. I book the aisle in the window and I hope the flight is like relatively empty and no one books that seat. Right.

[Jared Freid]

Okay.

[Jordana Abraham]

If they do, I will just offer. We'll offer the, the aisle. It's the best day of the, of the middle person's life because they get offered to switch with the aisle and no one ever declines that offer. No one's ever like, oh, yeah, yeah, I want the middle.

[Jared Freid]

No, I, I want to be in the middle of two people who love each other. No, no one wants that.

[Jordana Abraham]

Yeah. So then. And. And they also. And they also. No one wants the middle. Just generally. So they're happy to have gotten like a surprise of getting the aisle seat.

[Jared Freid]

Right. I don't know. I'd rather it be in the airlines. For me, I'd rather that decision go to the airlines rather than, you know, rando you. Because I'm someone who flies a lot. You're screwing over. There was someone that flies a lot that would have gotten that seat ahead of that middle seat lotto winner that you just awarded. You know, why do you get.

[Jordana Abraham]

I like to give back, you know.

[Jared Freid]

Yeah. You've taken away. You've taken from the rich and given to the. Yeah.

[Jordana Abraham]

It's not a good thing. Except for.

[Jared Freid]

Not for me.

[Jordana Abraham]

No.

[Jared Freid]

I'm the wrist in this scenario.

[Jordana Abraham]

Yes. Yeah. No, it's true. I guess it's sort of an move then. Sorry for all the, the, the high level Delta people. Yeah.

[Jared Freid]

Yeah. To high level Delta people. It's an move to the regular Jim and Joe. Yeah. It's wonderful. Yeah, you're a hero. Yeah. You're, you know, Robin Hood is a villain in some versions of that story. If you told it from another direction.

[Jordana Abraham]

Yeah. You know me, I'm always fighting against corporate. Agreed.

[Jared Freid]

So this is all to say, I get to my flight, it's 6:20 boarding. I go up to the desk. Hey. And it's two, you know, gate agents. And they're like, I say, hey, guys, I'd like to change my seat. And they're like, what do you want to do? All It's a pretty full flight. I said, they go, unless you want to move back, you know, it's a full flight. And I go, I do. I actually do. I'm a 19. I'm in middle 19, and I'd like to move back to 38 aisle, if that's okay. I really appreciate it. And I see the. I'm dealing with a guy, and then the woman next to him, the other agent, she's talking with someone else, and she turns to me as he's like, taking care of this to me for me. And she does the biggest eye roll I've ever seen.

[Jordana Abraham]

Why?

[Jared Freid]

Because she was dealing with other customers. And I looked at. I go, tough. I go, tough crew on this flight, huh? And she, like, laugh, you know, like, knowing, like, this flight is. And I know they hate this West Palm to New York flight.

[Jordana Abraham]

Another one of those.

[Jared Freid]

She's like, another one, right? And I go, tough crew on this flight. And she started laughing. And I go, well, thank you both for being so wonderful. And then I walk away. I have my new ticket, my new. Now I'm 38 aisle. And then I go to board, and, you know, they're boarding the plane, and I walk on, and there's the woman again. She goes, you have a new seat, sir. And she's upgraded me to aisle Delta comfort.

[Jordana Abraham]

Oh, wow, look at you.

[Jared Freid]

The only reason I bring this up is then I sit in it, and I'm in row 11, and I'm going, oh, my God, am I an 11A after all of that? It was like, it's supposed to be, but I was 11D, right? 11A is window seat, but I would be windows. So it all goes to show you, all you have to do is hate on your fellow man to someone else who gets the joke, and you will be rewarded.

[Jordana Abraham]

No, it's true. People love that. I'm sure flight. I'm sure it gives flight attendants a special sense of, like, excitement to reward those that they deem worthy.

[Jared Freid]

Look at you. You're in. You're giving. How good does it feel for you to give someone, you know, the aisle

[Jordana Abraham]

when they thought they were getting the middle, right?

[Jared Freid]

I mean, it just happened.

[Jordana Abraham]

For me, it's always great to give back to the community, right?

[Jared Freid]

So I made it back. We didn't crash. We're here. If you're out there and you want to come to a show, I am in Connecticut tonight. I'm going to be in Norwalk, Connecticut, and then I'm in Vegas. I'm going to Vegas, Los Angeles. Jacksonville, Austin, Cleveland, West Hampton Beach, Miami, Foxwoods, Portland, Maine. And I got a book tour coming up. There will be more details in the book tour. Walking Red flag. I'm holding it up on YouTube. Pre order. Pre order. Pre order. If you message me who you're buying it for, I'll send you a little cameo back for that person.

[Jordana Abraham]

I was even in one yesterday. How did they enjoy my presence?

[Jared Freid]

Was in one?

[Jordana Abraham]

Yeah, they were like, who is this?

[Jared Freid]

They didn't even have to buy another book. Yeah, they. They. So what's going on today?

[Jordana Abraham]

All right, we're getting. Should we get into our emails? We've got some good emails.

[Jared Freid]

Yeah, why not? Is. Is there anything else to talk about from last night? Last night was good. I. I had a great time.

[Jordana Abraham]

It was fun.

[Jared Freid]

The food was good. What's it. Do we want to plug the restaurant? Do we remember the name?

[Jordana Abraham]

I thought the service was, like, at this rest. It was. It was Masara on 26th and Par. Unbelievable service.

[Jared Freid]

Totally agree. Unbelievable service to the point where I was like, this is. They must be professional. Like, this must be the training ground for the. The Plaza Hotel. Like, I was like, this is unbeliev. They put the food down at the same time. Did you see the food production?

[Jordana Abraham]

Yeah, it was great. Great, great service. And like, with the drinks, maybe this is why I had to. I had two drinks instead. They were like. Usually at these things, you kind of have to flag down a waiter to, like, beg them to get you a drink. And they, like, came up to me and they were like, what do you. What can. What can I get you to drink? And then came back. Do you want another? Before it was even finished. And usually it will, like, unless you're sitting at, like, a regular dinner table, that's not really what's happening.

[Jared Freid]

Noticeably. Wonderful. The service at Masara, I agree with you.

[Jordana Abraham]

Agreed. Anything else from the dinner? I think that was. That pretty much covered it. It went well. No drama.

[Jared Freid]

That's it. If you're listening, Delta, we are open for business. We will take all of your ad

[Jordana Abraham]

money and we don't need to at an 11A.

[Jared Freid]

No, I listen. I can speak to the experience. Who could speak better to the. And I'm good to your people. I'm making jokes with the. You know, the gate agent.

[Jordana Abraham]

Yeah, I mean, Delta sky club. I used to joke that that was like, your home. You live there.

[Jared Freid]

I've had more weird things happen at Delta sky clubs that I can even, like, put my finger on. Like, it's like the amount of Stories I just, I come back with. I'm like, this is I, I, the Sky Club people. It's a particular brand.

[Jordana Abraham]

Well, now that you're doing a certain specific route, I'm sure you'll make friends with more of the, the Delta staff.

[Jared Freid]

Oh, I, I, listen, I. To be known as like, you know, my own person. To not just be a faceless person at a Delta Sky Club. What's better than that?

[Jordana Abraham]

A diamond medallion member.

[Jared Freid]

Well, I want to be the 360 member. That's the one that you don't know how to apply for. They just, oh, all of a sudden

[Jordana Abraham]

they grant it to you. You. It's like exclusive.

[Jared Freid]

Yeah, I, I'm really surprised you're not there yet. I, I don't know how to get there. I don't know what it takes.

[Jordana Abraham]

Right. Maybe if you have to ask, it's.

[Jared Freid]

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[Jordana Abraham]

All right, let's get into our emails.

[Jared Freid]

I'll read our first one.

[Jordana Abraham]

We've got a petty or prudent Hey J and J. Long time. First time. I love the pod and you and you both so much and really appreciate how you demystify dating. Look at us. We did it and die. Mysticist okay, I have a petty or prudent for you. I was seeing a guy my junior year of college around 2018. I'm 28 now, who I met in class. We exchanged flirty looks but didn't talk until we randomly matched on Tinder. We ended up hanging out about four to five times and hooked up at least three of those. We never went out in public and he just come over to watch a movie and smoke. Which in hindsight was a clear sign he wasn't serious. But the time I was excited about him. I tried to find him on social media but couldn't. At one point I found his Instagram and requested to follow him but it seemed like he declined it. I told myself maybe it was an accident. Then one weekend he was out of town and texted me that he missed me. I thought it was so cute. But it also pushed me to dig more online because something felt off. I searched his name on Twitter and found his girlfriend's profile. He was on a one year anniversary trip with her and she had just posted pictures. I confronted him and that was that. When I asked if he had a girlfriend, he just replied, what?

[Jared Freid]

Good work, buddy.

[Jordana Abraham]

Impressive wordsmith. I felt compelled to tell her. Looking back, I think my intentions were a mix of genuinely wanting her to know and also getting back at him. I messaged her on Instagram explaining that we had matched on Tinder, seen each other a few times, and hooked up. I tried to be respectful but clear. Two weeks went by and she never opened it. My anxiety built because I knew messages can go to a hidden inbox. And I also worried he might have deleted it. Eventually, I unsent the message. I was scared she'd see it later when I had already moved on and I needed to prioritize my own mental health. I was also nervous about how she might react. I still feel guilty about unsending it. For all I know, they could be married now and he's still cheating. So my question is, is it petty or prudent to contact the girlfriend when you find out you're the other woman? Does the intention or approach change that side note? My friends and I now call him Secret Girlfriend man to the tune of Secret Agent Man. Is that a song?

[Jared Freid]

Secret Agent Man. Secret Agent Man. So it be like Secret Girlfriend Man.

[Jordana Abraham]

Is this a song? That's a real song.

[Jared Freid]

You never heard that?

[Jordana Abraham]

No, I don't think so.

[Jared Freid]

Yeah.

[Jordana Abraham]

Love the pod. Thanks for all the laughs and advice. Unsent and unsettled.

[Jared Freid]

How do you feel about this email? I. I just got to wonder.

[Jordana Abraham]

So this happened back in 2018 is what I'm gathering. When they.

[Jared Freid]

Decade ago.

[Jordana Abraham]

When they were what, like the whole thing happened?

[Jared Freid]

Well, no, she's. She's not. A decade ago.

[Jordana Abraham]

Yes, it's eight years ago. Eight years ago. Right.

[Jared Freid]

But she's 28 now and writing about something that happened at college.

[Jordana Abraham]

Yes, the college part is important, I think. I think it somehow makes this less petty.

[Jared Freid]

Oh, so you think it would be petty if she did this with.

[Jordana Abraham]

I don't think it would necessarily be petty now, but I think it's even less petty in college. Like if. Now I think as an adult, if I. Like if this was this kind of situation, I think I'd be like, I'm not, I'm just gonna like, don't want anything to do with these people. But I think in college, especially when everyone's like in the same bubble, I think it's more important to like tell people about stuff. And also it's just kind of like a weirder move in such a more close knit area. Do you know what I mean?

[Jared Freid]

Right. I guess, I guess my view on this is the opposite. Like if she was 28, met a guy on an app and then she goes to search him and finds out he's on a vacation with his girlfriend for their one year anniversary and then she sends a message with like a kind of doing like the casino dealer, like brushing their hands above the table, like let me just get out of here and let all parties know because I don't want to be murdered by their lover who's been scorned. Like that to me is like a prudent move at 28, really, you know, like, hey, I, I matched with your boyfriend.

[Jordana Abraham]

I think at 28 the stakes are higher though. Like a 28 someone that you're on a one year anniversary with could be someone that you're like maybe going to marry or get engaged to in the next year or two in college. So when you're 28 and you're on your, you're on your one year anniversary with your college girlfriend, it almost seems like, I don't know, drama just seems, the drama of, it just seems less weird in college than after.

[Jared Freid]

Right. I think the drama in college is more like fun to add to the mix of college.

[Jordana Abraham]

Right.

[Jared Freid]

You know, like that's why I think

[Jordana Abraham]

it's less petty, I guess. But not, I don't think it's necessarily either. I don't think it's petty necessarily at 28 either. But I also think it's interesting.

[Jared Freid]

I'm trying to separate the petty from the petty imprudent of it is different to me than a 28 year old writing into this podcast eight years later being like, it still haunts me. I still feel guilty about unsending it. For all I know they could be married now and he's still cheating as if this is her like right white whale that she hasn't caught yet that's murdering people around the city. I don't, I don't know, I'm like, I can't believe this is still on her mind. I, I, I like, like I'm with you because they were in college. It's like this like, okay, I'm willing to believe that like they were on a one year, you know, like their relationship is not as, like, there's not as much going on there, you know, like, it's a college relationship.

[Jordana Abraham]

Doesn't feel as serious. Yes.

[Jared Freid]

Right. And which is why sending it then is, is like, I get, I don't find it petty. I, I just find it prudent for like, hey, I'm just telling you the story as I know it. And we might know friends in common and I don't want to be known as the cheater. This is something that happened totally by, by accident for me. And I, I just want to make sure I'm out. Like, to me, when there's a fire in the house, I run away, get

[Jordana Abraham]

out of the house. But it's interesting, like when she confronts him about the girlfriend and he says, what? That's very college. And just like, But I think, like, I think she has to admit that part of the messaging of the girlfriend is a little bit like revenge against this guy for not even having like.

[Jared Freid]

Sure.

[Jordana Abraham]

The respect to like articulate a real response to that.

[Jared Freid]

Right. I mean, yeah, he lied. He lied in three different occasions to her without lying, you know, like.

[Jordana Abraham]

Yes.

[Jared Freid]

And then when she asked him have known whether he's, he just replies, what? What?

[Jordana Abraham]

Right.

[Jared Freid]

So she's like, it's a great answer. It's a. Yeah.

[Jordana Abraham]

Fear no woman.

[Jared Freid]

It's not a lie. Fear no woman.

[Jordana Abraham]

Like, woman scorn. But also more than that, fear no woman. Like a woman who doesn't have closure. That's why when you were telling me about, like when you had to text people saying that you were in a relationship, you got great responses. Yeah, those people love that. If you had just, if someone had said, oh, it looks like you had a, if let's say you never messaged anyone that you were dating or had dated at the time, and then they messaged you and were like, looks like, it looks like you're like with someone. Like, what's going on? And then you replied what? That person would be like, furious with you and kind of have nowhere to put their irritated energy. And then they might message your girlfriend.

[Jared Freid]

Right. I, I just can't believe the writing to the I, When I read this, I was like, you're 28 and you're still talking about this guy from college. I, I, that's, this is where we, this is where we differ, men and women. Yeah, I'm like, like, like to me it's like, ah, you know, win some, lose some. That Was in college, whatever. This woman, like, let's say she like, was like, went back to the woman and DM'd her again. It'd be like knocking on the door. Like they're like together and they're like, right. That'd be crazy. It's like showing up to their house and she's like, he cheated on you in college from Tinder. And then the wife is like holding their two kids.

[Jordana Abraham]

Right?

[Jared Freid]

And she's like, ma', am, we're good. That was college. Like, right? What are we going to do? We're in this. And then she's like, well, well, in my, in my Facebook group, we discuss things like this. Like, she would look crazy.

[Jordana Abraham]

I don't think she would do that though, right?

[Jared Freid]

Well, let's hope not. She wrote this is one step away.

[Jordana Abraham]

Yeah. I also think there that the girl that she messaged saw it. She just didn't let you know she saw you saw it. She did not see it. No one misses that message unless they have 6 million followers, right?

[Jared Freid]

No, no, no. I, I'm. You and I have come to the same conclusion. She saw it, she handled it in the way she wanted to handle it. It didn't need to involve you. I think a lot of people when they're told they're cheated on or get told information that is embarrassing to them, they want to keep that group small. And this woman was like, I'm gonna

[Jordana Abraham]

keep this group small, take this information between and silently do what I need to do with it.

[Jared Freid]

And maybe it ended with her breaking up or maybe it turned into her having a talk with him. Maybe they did nothing and maybe she's just with this guy and she's very happy in that relationship and he's a better guy now or a worse guy. We have no idea. But like, that's not her responsibility.

[Jordana Abraham]

Right.

[Jared Freid]

Like petty would be to go back and remess. Hey, I don't know if you saw

[Jordana Abraham]

eight years ago, right.

[Jared Freid]

When we were in college, but I just want to reiterate. I slept with your boyfriend when you guys were first starting.

[Jordana Abraham]

Yeah.

[Jared Freid]

Who in college is going on a one year anniversary? That's another guy made him money.

[Jordana Abraham]

That's another good question. Yeah. What? I'm gonna start using that when everyone and anyone asks me why I. If I did anything that I don't want them to know that I did.

[Jared Freid]

Well, it's a strategy I use for hecklers.

[Jordana Abraham]

What? Speak up.

[Jared Freid]

I always say what? Speak up. Say it again. So when someone heckles you, have them say it again. They have to own the words.

[Jordana Abraham]

Okay, I'm going to use that on Mike when he asks why my closet is. Why my my closet is so messy.

[Jared Freid]

What? Right? And then he'll have to go, why? I said, why is the closet so messy? Like, if you're not embarrassed, if you believe in what you say, you will double down. If you half don't believe it, you look bad right away.

[Jordana Abraham]

Right?

[Jared Freid]

So a heckler. If they're like, you suck. And I'm like, I'm sorry I missed what you said. Well, you suck. You know, like, you could. There's a change in the voice, but it's generally not you suck. It's like someone making a comment. Then I get time to think. What gives you time to think?

[Jordana Abraham]

Yeah, I think they give that advice too, to, like, kids for like a bully or someone who, like, says something mean to them. If you say like, like what? Could you say that again?

[Jared Freid]

Like, then they have to say it again.

[Jordana Abraham]

Yeah. If you can say it again, that's different.

[Jared Freid]

You must really fucking mean it. Yeah. Focus Features in Blumhouse present Obsession.

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[Jared Freid]

Be careful. I wish Nikki love me more than anyone in the entire world. Who you wish for? Obsession is 96 fresh on rotten tomatoes.

[Jordana Abraham]

I love you so, so, so, so much.

[Jared Freid]

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[Jordana Abraham]

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[Jordana Abraham]

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[Jared Freid]

All right, let's do another one. I I this next one, I think is a very interesting email.

[Jordana Abraham]

Yes. All right, read it.

[Jared Freid]

Jared And Jordana Obligatory love the show. Lol. I binge on my monthly work road trips. Jared, congrats on the girlfriend. Jordana, congrats to you and Mike on becoming parents. It's been fun hearing the ebbs and flows of life through the podcast. I'm a 32 year old single guy, six two 185 pounds living alone in a.

[Jordana Abraham]

I have no idea how much

[Jared Freid]

a man, I have no idea how

[Jordana Abraham]

much a man should weigh at 6:2. What is that, what is that saying?

[Jared Freid]

Should. There's no should to me what that

[Jordana Abraham]

says about what that's a skinny guy that says about a man.

[Jared Freid]

Well, I'm not 62 185. I am shorter and heavier than those two. I'm, I'm in the, the bad direction for both.

[Jordana Abraham]

Right? Usually listeners don't write in with their weight.

[Jared Freid]

I will say no, but I, I think it does tell us everything about this.

[Jordana Abraham]

Can you imagine a woman writing it?

[Jared Freid]

I mean from now on, if you want to write in with your height and weight, we'll take it. We'll, we'll, we'd love to hear it. Yeah, I think it's great.

[Jordana Abraham]

Funny.

[Jared Freid]

62185 I, I mean I'm looking at a guy 62185 type in the chat GPT. Show me a guy who's 62185.

[Jordana Abraham]

Okay.

[Jared Freid]

Joe's 622-10. Yup. Yeah, skinny Joe.

[Jordana Abraham]

Okay.

[Jared Freid]

Not to say Joe's overweight. Joe looks great, but this is like Skinny Joe.

[Jordana Abraham]

Right? Okay, got it. All right, anyway, continue.

[Jared Freid]

But again listeners, if you want to write in with your height and weight, we will take that and make as awkward a conversation as possible as you see. But also it did tell me something. When I saw that I was like we are in for a very specific email.

[Jordana Abraham]

Yes.

[Jared Freid]

Living alone in a mid sized Midwest City around355,000 Metro.

[Jordana Abraham]

I think that's saying how much he's making.

[Jared Freid]

350, 000. No, 350 000.

[Jordana Abraham]

Okay. Oh, I thought that was his salary. Okay.

[Jared Freid]

No, No, he's making, he's in the worst direction there, I promise.

[Jordana Abraham]

Okay.

[Jared Freid]

I have a solid corporate design job, great co workers, strong roots here, so I'm not looking to move. I'm also finishing paying off some credit card debt from a past relationship in the next six months. Lesson learned. Don't buy a house together before you're engaged. I'm laid back, social and good at conversation. In my late 20s I had no problem getting dates. But now newly single Again, both the quantity and quality. Who I. Who am I to judge? Feels different. Well, he says who am I to judge? But he's judging. He's judging.

[Jordana Abraham]

But I like that he said that because he's like, I have this feeling. I know it's. I know it's kind of icky, but like I still have the feeling, which I think is accurate for most people.

[Jared Freid]

And that's how he feels. In 2026, I've gone on six first dates. Women 30 to 32, no second dates. He's now going to give us the stats on the women. You ready?

[Jordana Abraham]

Yep.

[Jared Freid]

One out of four. Oh, on 14 on January 4th.

[Jordana Abraham]

Yeah. We're having a hard time. Having a hard time with the stats. I thought that was that the amount of people in his city was the amount of dollars he makes in a year. You thought he's ranking the woman as a one out of four?

[Jared Freid]

I. Okay, let's. January 4th, he goes on a date with a 31 year old media director. Coffee? I planned and paid 25 plus five dollar tip equals $30. Good convo. No, thank you. Not feeling the connection. He puts in quotes. So I'm taking that as she said, I'm not feeling the connection for a second.

[Jordana Abraham]

Yeah.

[Jared Freid]

January 21st, 30. School administrator. Drinks. I paid 35 plus eight dollar tip. 43 bucks. Felt like an interview. She said let's be friends, still text but won't meet.

[Jordana Abraham]

Okay.

[Jared Freid]

Okay. On February 6th, he went out with a nurse. Drinks.

[Jordana Abraham]

I paid 32. The nurse. The nurse is 32 years old.

[Jared Freid]

Oh, 30. On February 6th, he went out with a 32 year old nurse. He had drinks and he paid $68.00 plus $13.00 tip. 81 bucks. Great chemistry. Made out. Then she took a call and ghosted. Did you take that as meaning she like took a call during the day?

[Jordana Abraham]

Sounded like that. Right. Like, did she not come back?

[Jared Freid]

Made out. Great chemistry. Made out. And then she's like, hold on, someone's calling me from the hospital. And showed up again.

[Jordana Abraham]

Yeah. Did she leave?

[Jared Freid]

I don't know for. He's been pretty specific with everything, but.

[Jordana Abraham]

Right.

[Jared Freid]

That's a little vague.

[Jordana Abraham]

Okay.

[Jared Freid]

Okay. February 27, 31, he went out with a 31 year old curriculum admin split drinks, $12 and a $5 tip. $17 was total to him. Low efforts, said not interested at the end.

[Jordana Abraham]

Split. Now he's starting to split drinks. He's getting frustrated.

[Jared Freid]

Right.

[Jordana Abraham]

By 2:14, he's paying for all of it. 227.

[Jared Freid]

Yeah.

[Jordana Abraham]

Let's see. Split. Okay.

[Jared Freid]

Anything you want? Okay. The top half of the menu. Okay. We're going to split this. Yeah. March 14, 33, disability coordinator. They went on a St. Patrick's Day crawl. She planned. We each paid our own 30, $32 plus $12 tip for 44 bucks. Fun day. No physicality. She chose someone else.

[Jordana Abraham]

What does that mean? She chose some. Like she texted, I'm seeing someone else.

[Jared Freid]

That's the only reasonable.

[Jordana Abraham]

Sure.

[Jared Freid]

Either way I could see it. And then March or April 3rd, she. He went out with a 32 year old account manager. Drinks. I paid $46 plus ten dollar tip. 56 bucks. Great convo. Lots in common. She said it was her funniest day. Drank three wines while I had one. No thank you quote, not feeling a romantic connection.

[Jordana Abraham]

Interesting. He's noting the thank you. Who said thank you and who didn't?

[Jared Freid]

Oh, right. Did he say that in the other ones too?

[Jordana Abraham]

He said that in a different one also.

[Jared Freid]

Right. He notices when they say thank you.

[Jordana Abraham]

Yes. All right. It's Midwest. He's into manners.

[Jared Freid]

Listen, if someone didn't say thank you, there'd be times I'd notice it.

[Jordana Abraham]

I would always say thank you no matter what. Personally, that's just, that's just polite.

[Jared Freid]

Right. I would too.

[Jordana Abraham]

Anyway, go on.

[Jared Freid]

Why not? Yeah, I'm pretty traditional and assume I'll pay, especially if I plan the date. But I'm getting frustrated spending time and money for what feels like one hour evaluation. The rejection texts also feel a bit hollow. So what are women 28 to 35 actually looking for right now? It feels like people are holding out for something better or avoiding settling. Am I coming off too friendly and not building enough romantic tension? What's the balance between being assertive and versus leaving them wanting more? Or are women in this age range just slower to commit, appreciate any insight, discourage dream?

[Jordana Abraham]

Yeah.

[Jared Freid]

What do you think?

[Jordana Abraham]

I don't think anyone would say that women 30 to 33 are slower to commit than other age demographics. I would say I would eliminate that one right off the bat.

[Jared Freid]

Well, 28 to 35 especially. Yeah, like that is prime time. Everyone's getting engaged. The, the, the people on the island are getting saved before me. Everyone's disappearing. Where is everyone this weekend? Oh, everyone seems to have an in law thing. I, yeah, I, I, I'm with you. Do you want to go through those questions? It feels like people are holding out for something.

[Jordana Abraham]

Yeah.

[Jared Freid]

What do you, what's your feeling on this? Give us the female perspective here.

[Jordana Abraham]

For this guy that I'm assuming because he's writing about how like frustrated that he is spending time and money for what feels like these one hour evaluations. I'm assuming he's giving off that energy of being like frustrated and irritated and sort of like having this transactional feeling or the fact that he even knows the exact amount he paid and the amount he tipped for each of these dates. He's like making this into like an ex. And I think this is, this email seems very male. It's very like laid out in bullet points. There's, you know, he's trying to let the facts speak for the, the emotions. But I think if he's bringing that energy to a date, I think whether you, whether you're, it's obvious or not, I think people can sense that, that there's like he's bringing a level of transaction to the state so they're feeling transactional.

[Jared Freid]

Right. And he's saying all the things that no matter what your gender or what you're looking for, people say, like he's, he's kind of moving towards writing a blog. You know, he's Carrie Bradshaw. Right now it feels like people are holding out for something better or avoiding settling. Like that's one of those things that people say that you can tell they're trying to have like this interesting opinion on what's going on. But if you've been in dating talk land long enough, you've heard this every week, every day, every of every week for the last 10, 15 years. Like, yeah, none of that is an interesting opinion to me. I also don't think it's accurate saying that. Right. Especially considering, you know, am I coming off too friendly? You know, no one would say I didn't commit to that guy because he was too friendly, not building enough romantic tension. Like these are things that like, you can't do, you know, like, they're not even fixable things. Like with some people you just have no romantic tension. It just doesn't happen, you know, it's a match thing, you know, like.

[Jordana Abraham]

No, I agree. And I, I think he just needs, I think if he's, if there's anything that he's trying to change, I would just change the expectations out of these dates. Because I think people can say, like, if you see this with women a lot too, where it's like, if you go on the date and it feels like this date was a failure unless I met my husband or I, you know, I wasted putting on an outfit and doing my hair, that's not that, that's an energy that you think is like, separate from the date, but you bring it into the date.

[Jared Freid]

Right.

[Jordana Abraham]

And I think with this guy, he's feeling like, how much am I paying? What am I getting out for, how much money I'm putting in? He's thinking of it as, like, a math equation, when really he should just think of it as, I'm. I'm going to. I'm going to drinks with someone. I'm going to have a conversation. Let's see what happens.

[Jared Freid]

I totally agree with everything you said. And, like, I read this and I said my. I had one. Like, if I was to make a. A, A, A billboard for him, it would say, delete the apps. Like, it's time. And we all have that time. Like, I've been there, but I, you know, Jordana, you've been there. You know, when. When you were on dating apps, you, You. There's a moment. I think there's subtle things people say and do that aren't as, you know, ripe for being taped for the Manosphere documentary.

[Jordana Abraham]

Yes.

[Jared Freid]

That make you. You just sound a little bit like you've had it, and that's okay.

[Jordana Abraham]

And he has.

[Jared Freid]

We've all had it.

[Jordana Abraham]

Because he has had it.

[Jared Freid]

Right. He's been on these dates that he thought were pretty good. I mean, like, even when you say that, the rejection texts also feel a bit hollow. Like, my feedback to that is, like, what would you like your rejection after one date? Like, right. What would you. What would you like said? Do you want a full review? What do you. They're not your boss. They're not gonna give you a company review. They don't know you enough. And they also. They don't have the right to. You are you. You are. Great. It'll be fine. But I think this person is in need. I. I actually wrote down subtle things. People say that. I. My first inclination is they should delete the app.

[Jordana Abraham]

Okay, let's hear it.

[Jared Freid]

When you start tallying your losses, like this guy. Like this guy. Delete the app time. It's time.

[Jordana Abraham]

When you have a spreadsheet with. With meal price plus tip. Why don't you just say the whole about you paid. Like, why do you have to break it down?

[Jared Freid]

He's telling us he's not a bad guy. He's trying to let us know I tipped the appropriate amount.

[Jordana Abraham]

Wasn't doing the calculations right.

[Jared Freid]

Well, he's putting the math on good guy, bad guy. You know, he's putting. He's. Again, as you said, he's letting the math speak for the emotion.

[Jordana Abraham]

Right.

[Jared Freid]

So look at I tip and I tip well, you know, so it's like, yeah, but nobody wants to fuck a good tipper. You know? Like, it's like, no, not everyone has to. Just a good tipper does not always get.

[Jordana Abraham]

Right.

[Jared Freid]

That's what my grandma always said. So.

[Jordana Abraham]

Okay.

[Jared Freid]

You know. Well, you also don't tip to get. That's not why you tip.

[Jordana Abraham]

Yes.

[Jared Freid]

So the fact that he's showing us kind of says a lot about where his headspace.

[Jordana Abraham]

The transactional nature.

[Jared Freid]

Change of perspective.

[Jordana Abraham]

Yes, Transactional nature that he's looking at this with. Okay, okay.

[Jared Freid]

So another person who should delete the apps is when you say the app isn't showing me the good ones.

[Jordana Abraham]

Okay. Yes. A lot of blaming the app for your problems. Yes.

[Jared Freid]

Blaming the app and saying, well, the algorithm. If you even say the word algorithm, delete the app. If you've ever said the word algorithm in relation to a dating app, delete the app. Because it's actually a crazy thought, the idea that the app thinks of you specifically to not show the good ones to.

[Jordana Abraham]

Right. The app is out for you.

[Jared Freid]

Right. You're just getting the people. You get what you get you. If. If there was no app, you'd get nobody.

[Jordana Abraham]

Like, it's Right.

[Jared Freid]

This idea that there's this like section that like, only the hot people are getting is crazy. So delete the app. Any mention of wasting time when it comes to first dates, you need to delete the apps.

[Jordana Abraham]

Yeah.

[Jared Freid]

Because at that point, you're talking about the apps as if you are forced to be on them. No one's forcing you to be here. You can just not be on them. You're wasting your own time every time you open up the app and you're doing it miserably.

[Jordana Abraham]

Agreed. It's better to not go on a date than to go on a date with a shitty attitude. Because the other person can smell that.

[Jared Freid]

Totally. And I think that's probably a lot of his problem. And then the last one I wrote talking about people with words one would use for a economics equation. So if you use the word low effort, quality, low effort, scarcity, supply, demand, fiscal policy, any of those phrases, you should delete the data guys apps.

[Jordana Abraham]

Yeah, I think he needs to. To delete the dating apps. Work on his attitude towards dating because,

[Jared Freid]

well, he's probably wondering, how do I do that? Well, this is my next piece of advice. You ready?

[Jordana Abraham]

Let's hear it.

[Jared Freid]

He needs to plan a hangout with friends. He needs to delete the apps and plan a hangout with friends. He needs to Kind of get back to his roots. He says he has strong roots there. I think he's kind of lost it a little bit. I think he needs to get back to like, how he acts with his friends and where he's at his best.

[Jordana Abraham]

Yes.

[Jared Freid]

You know, like, do a barbecue, go get together, do something with a larger group of people where you can just kill a social interaction. Let's get a win here. And I think you'll feel good.

[Jordana Abraham]

I also think he needs to process this breakup a little bit more because he's saying he talks about the breakup. When he talks about the breakup, he talks about he's finishing paying off credit card debt from the past relationship in the next six months. Lesson learned. Don't buy a house together before you're engaged. Okay. It sounds like there's some like, unprocessed, lingering financial resentment towards women going on here. Right. Which you can see in the way he's dating. Like he's now like sort of. He seems hyper fixated on like the spending to relationship outcome thing. And maybe that's left. Maybe that's some left over from his ex.

[Jared Freid]

Right. And if he wrote it in the email to us, I'm willing to bet he has mentioned the ex who he bought a house with on the first date. Which I'm not saying that's off limits for a first date conversation, but it's all on how you say it.

[Jordana Abraham]

Right.

[Jared Freid]

If he's saying it to us, it's like, lesson learned. No one wants to hear from lesson learned guy.

[Jordana Abraham]

Yes.

[Jared Freid]

You know when you say lesson learned, you're saying I up my life. I went in the wrong direction back there. You're not really saying I'm happy for having the experience and knowing more, you know, and being better off.

[Jordana Abraham]

Yeah.

[Jared Freid]

Your lesson learned is like a miserable way to say something that could be said more positively.

[Jordana Abraham]

Agreed. I think he's bringing that energy into there again, whether he knows it or not. Just the fact like that he's like auditing these dates to me means he's got some like, weird financial that, that I think would be good to, to deal with before he even begins to date again.

[Jared Freid]

Totally agree. Hold on. I, I just. The, I was listening to you. The, the cord came out of my computer. Hey, I am an old man now, huh?

[Jordana Abraham]

When did it happen?

[Jared Freid]

I don't know when it happened. It's all this flying I in 11D. I should have been. My back hurts. No.

[Jordana Abraham]

Now didn't I get.

[Jared Freid]

I agree with everything you said.

[Jordana Abraham]

I'm sorry, do you use the thera. The mini thera travel. Theragun that I got you for the holidays from ubereats. I think that'll help you.

[Jared Freid]

I think you're right. Well, yeah, I gotta. Gotta do my stretches, maybe. Well, we solved dating again. Jordan.

[Jordana Abraham]

We did it. Good luck to the people who wrote in. Thank you for writing in and we'll be back next week.

[Jared Freid]

Boom.

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