He’s 24, I’m 37 - Can We Really Be In Love?

Summary

U Up? – “He’s 24, I’m 37 – Can We Really Be In Love?”

Podcast: U Up?
Hosts: Jordana Abraham & Jared Freid
Date: January 30, 2026

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Main Theme / Episode Overview

This Friday Feels edition of U Up? is both a milestone and a send-off episode, marking Jordana’s last day in the studio before maternity leave. Alongside some personal reflections about parenting anxieties, nanny discourse, and relationships, Jordana and Jared dive into listener questions. The centerpiece: a candid and humorous discussion about a 37-year-old woman dating a 24-year-old man, and navigating the early stages of possibly falling in love across an age gap.

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Key Discussion Points & Insights

1. Jordana’s Maternity Leave and Parenting Fears

(Starts ~04:03)

• Jared asks Jordana her biggest fear about having a child.

  • Jordana: “I think a health issue is probably my number one fear. Not knowing.” (04:09)
  • She notes anticipatory stress as a recursive thing—there’s always something to worry about as a parent.
  • Both reflect on how many people seem ill-prepared for parenting but still manage, including themselves.
  • Jordana’s privilege in affording help eases some fear, and she discusses growing up with a nanny (Josephina).

• Nanny Talk:

  • Both hosts recall their own childhood experiences—Jordana with a live-in nanny until age 8 or 9, Jared with women who looked after the kids and housework.
  • They address social discomfort and different expectations (Jordana’s husband grew up with a stay-at-home mother, leading to cultural differences in household help).

2. Listener Email #1: "Petty or Prudent?"—The $20,000 Breakup

(20:05–28:03)

• Email Situation:
  A woman shares her story: after moving cross-country for her much wealthier boyfriend (at his request and after accepting $20k as “compensation”), she broke up with him three months later. He then sent a scathing email about her not returning the money. She Venmoed him $5k (limit), offered to pay back the rest, but he told her not to send more. Is she petty or prudent for keeping most of the money?

• J&J’s Breakdown:

  • “It sounded like he wanted her to offer the money back as an ‘I’m sorry for breaking up with you’ thing.” – Jordana (22:24)
  • Jared interprets it as an ego wound for him, likely compounded by social perceptions of the age/money imbalance.
  • They agree:
    • She’s not obligated to return the money; the compensation served its intended purpose for the move and her independence.
    • Offering to return it would have been a nice gesture, but actually demanding it is petty.
    • “The whole intent of the money was for the move or to try it out.” – Jared (25:38)
  • Both note his request was more about villainizing her post-breakup than actual financial need.

3. Lightning Round: When Do You Know You Love Someone?

(28:33–30:07)

• A listener describes marathon dates (13–21 hours!), quick onset of intense feelings, and a lot of sex—with the caveat that she’s 37 and he’s 24. She wonders about when to say “I love you,” especially given that he says things like “I love spending time with you.”
• Jared jokes: “The minute they give you $20,000.”

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Main Event: “He’s 24, I’m 37…” Navigating a Large Age Gap

(30:11–39:19)

The Listener’s Situation

A 37-year-old woman has begun a whirlwind romance with a 24-year-old man. They share interests, spend marathon hours together, but he hasn’t dated since he was 18. She admits to feeling unexpectedly in love and asks for advice about saying “I love you,” and for the hosts’ thoughts on the relationship’s prospects.

J&J’s Detailed Analysis

• Initial Reactions:

  • Jordana: “I thought she was gonna talk about some crazy anal…like sex situation. 24? No, this is cool.” (30:13, 30:44)
  • Both are amused but supportive, with Jordana’s discomfort providing comic relief.

• On Age Gap Stereotypes:

  • Jared: “This might be you and him. This is your story…You could be Demi Moore and Ashton Kutcher.” (33:39)
  • They acknowledge age differences add complexity, but “anything can happen.”

• On Saying “I Love You”:

  • Jared: “I don’t know if you can count on his ‘I love you’ to be the same as your ‘I love you.’” (34:19)
  • At 24, he may mean “I’m having a great time” rather than “I’m ready to commit long-term.”
  • Jordana: “He’ll say it back. Why not?... I don’t know if it means anything.” (35:07, 35:14)

• Advice on Expectations:

  • Don’t read too far into “I love you”—it doesn’t equate to aligned life stages or intentions.
  • Jared: “You’re on planet Earth and he’s on, you know, a totally different one…The gravity is different for both of you.” (38:17)
  • At 37, your life may be more planned, with readiness for next steps. He’s likely just starting out.
  • Ask direct, practical questions about the future if concerned—focus on tangible plans, not just words.

• Notable Quotes:

  • “At 24, you love everything. You’re just having fun... at 37, things are a little more practical.” – Jared (34:19)
  • “I don’t think he realizes the consequences of his words.” – Jordana (37:26)
  • “Two ‘I love you’s are not created equal.” – Jared (37:50)

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Memorable Moments & Quotable Lines

• On Nannies:
  • “Why do you think I have relationship issues? Josephina, it took us eight years to get to this hard-hitting episode with all this information.” – Jordana/Jared banter (13:10–13:20)
• On the $20k Email:
  • “He only wanted it so he could hold onto something to villainize her for.” – Jordana (26:51)
• On Age-Gap Romance:
  • “He could, I think, likely say it back. Probably doesn’t mean the same thing to him. Wouldn’t put much stock in it.” – Jordana (35:14)
  • “Two I love you’s are not created equal.” – Jared (37:50)

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Timestamps for Key Segments

• Parenting Fears/Nanny Talk:
  04:03–16:03
• Listener “Petty or Prudent?”/Breakup Money Debate:
  20:05–28:03
• Lightning Round (“When do you know you love someone?”):
  28:33–30:11
• Main Age-Gap Email & Discussion:
  30:11–39:19
• Closing Remarks:
  39:19–end

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Tone & Takeaways

Consistently candid, warm, and witty, this episode is marked by Jordana’s vulnerability (parenting stress, cross-cultural marriage quirks) and Jared’s playful but honest insight into gender and age dynamics. Their advice consistently centers around being self-aware, realistic about intentions (especially with significant age gaps), and direct in communication—tempering hope with a healthy dose of realism.

As the episode wraps, both hosts wish Jordana well on her maternity leave—and remind listeners that love, like life, is rarely as simple as an “I love you.”

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For More:
Find U Up? on Instagram @u.up.podcast and subscribe for bonus content.

Transcript

[A]

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[B]

Hello, Jordana. Leaving soon. Going to have babies. Goodbye, Jordana. Have your babies and enjoy cleaning up their poo.

[C]

Thank you.

[B]

This baby is going to be the best thing that ever happened to us.

[C]

To the studio. Hello and welcome back to the Friday Feels episode of the U Up podcast. I'm Jordana Abraham.

[B]

And I am Jared Freed. It is so good to be back here with you, Jordana. It is a day of mixed emotions for all of us.

[C]

Here it is.

[B]

We're excited for a baby to be on the arrival, but we're also sad to see you go. This is the last day.

[C]

I feel bittersweet too. It's tough. I mean, we, we will. I will be here for the benefits.

[B]

So for anyone listening, if you're not a benefit subscriber, I think our benefits episodes are awesome. Yeah, they're heartfelt and they're gonna be.

[C]

Even better while I'm gone because I'm gonna not have spoken to you guys. So I'll have a lot to talk about.

[B]

We have a lot to go over on these benefit episodes, so we want you guys to sign up for benefits. It's five bucks a month. It gets you two extra podcasts a month. You'll get to hear from Jordana on her mommy, mama, mama. Hey, mama journey. Yeah, a little mama journey that she's on. And you'll get to hear me ask stupid questions. So.

[C]

Yes.

[B]

Yeah. And plus, you get the episodes a day early. No ads. It's all, There's a lot of perks.

[C]

Definitely worth it. And it's also, I do say so myself.

[B]

Right? And we have ads on the show. You know, how do you pay for the show? How do you give back to a show that's, you know, we give a lot to you. I, I, I, I feel confident asking because we do YouTube, we do podcasts. If you feel that this could be a way of feeling good about, you know, an exchange of goods for services type of deal. Sign up for the benefits. You know, I think you'll enjoy it.

[C]

And also, you know, post about us.

[B]

Tell a friend, do that, all that stuff. We want, you know, comments, concerns. Can I ask you a question?

[C]

Yeah, let's do it.

[B]

What is the thing that scares you most about having a child?

[C]

Okay. Yeah. No, it is a good show, right?

[B]

I. I'm sitting here. I'm not even close to having kids. Not even a little bit close to even being engaged. I'm not even a little bit close to being in a relationship. I'm not even close to calling someone. Someone I love. So why don't you tell us? You are way ahead of me. Way ahead of me. Anyone out there, what are the fears that I'm with them? No, no, no.

[C]

If you're listening to this, I mean, who knows? We're recording this a little early. By January 30th, you could be engaged.

[B]

I could be with woman.

[C]

You know, it's happened before.

[B]

It's happened. Weirder things have happened.

[C]

Yeah.

[B]

If you're listening now, I'm in Boston. Boston added a second show. I also have shows coming in Dallas, Houston. Come to the show before we get to Jordana getting deep with us about how scared she is to have a kid. I am also.

[C]

Did I say that?

[B]

Oh, okay. Toronto, Vancouver, the. Cool. I'm coming to the COVID I'm coming all over the Couve and then Tempe and La. Los Angeles. Netflix is a joke festival. I'll be part of it. Saturday night show, 9:45 downtown. Come assemble the group chat. What are you most afraid of?

[C]

I guess there's a few things I. I'm most afraid of, like, I think a health issue.

[B]

Okay.

[C]

I think is probably my number one fear. Not knowing.

[B]

How many times does that, like, happen, you know, you know, flow over your body?

[C]

Because I, I've had every, like, scan, I think.

[B]

Every scan.

[C]

Yeah. Well, that's. I mean, even, like, that's just before, like, once they're born.

[B]

Right.

[C]

There could be other stuff that they don't even know about, I guess.

[B]

Right. So that's a fear.

[C]

I would say that's more fun fears. That's the.

[B]

That's the biggest anymore, I guess.

[C]

My, my.

[B]

That just scared the. Out of me.

[C]

Oh, sorry. I don't know. I mean, like, that's my real biggest. The biggest fear. That's like the. Yeah.

[B]

But I guess I guess I've never known how much that would hit me.

[C]

Well, it didn't really hit me until, like, it felt like it was like, really happening. And then I was like, well, who knows what Again, it's more like, I don't know what I'm gonna get.

[B]

Well, it's also. It's all, you know, Dr. Naomi kind of talks about. This is like, I've. I've heard her talk about this idea of, like, when you're stressed about something, you just, like, find a new thing to stress out about.

[C]

Right.

[B]

You know, like once. Oh, we're having a baby now. What if they're not help. You know, like, it goes to the name.

[C]

Yeah, I'm sure.

[B]

That hole.

[C]

It's always something. And I'm sure even if they're healthy, what if they're not this or that or whatever.

[D]

Right.

[C]

So it's always something, but that feels.

[B]

Like they're not cool and.

[C]

Right. What if they're annoying?

[B]

Yeah, what if they're annoying? What if they don't like the shows I like? Right, right. What if they be spread ketchup on fries without.

[C]

They don't like to play games.

[B]

Yeah, you like games. You're a game family.

[C]

What if they don't like the sun?

[B]

I would kick them out of the family. You don't want to go to the beach?

[C]

Yeah, no, I think. I think. I guess my other fear is that I don't know. What. I don't know. Like, there's going to be some, like, horrible part of it that I, like, haven't even thought of because I've never done it.

[B]

Right. So doesn't it make you feel better, though, that, like, some of the dumbest people you've ever met have had kids?

[C]

Oh, 100%.

[B]

Right. That. That's got to be the running. The running policy of a family is like, we're not a teen mom.

[C]

Right.

[B]

You know.

[C]

People. But, like, I feel lucky enough to be able to, like, afford someone to help me also. That's a big part of it. I think that eases the, like, the feeling of being afraid of.

[B]

But you'll never see them in the pictures. Don't worry. Jordan is going to act like she had.

[C]

No, I'm going to pretend that I did it all on my own. No, I'm very open about.

[B]

I. Those people are the funniest people to me.

[C]

Very pro nanny.

[B]

Yeah. Pro nanny. They better be in the.

[C]

I was raised by. By nanny. She made me. The only reason I'm somewhat semi normal is.

[B]

What was the nanny's name?

[C]

Thank God my parents outsourced that. Josephina.

[B]

Josephina.

[C]

Yeah.

[B]

Did you ever keep up? You ever.

[C]

I saw her. She Came to my. My dad's like, sh.

[B]

Come on.

[C]

Yeah.

[B]

What was that reunion like? Were you like, I'm pregnant. I'm about to have a Josephine?

[C]

Yeah. It was crazy because, like, she came, like, basically started working for my family when I was, like, my mom. When my mom was, like, just pregnant with me.

[B]

Well, your mom also. Working woman gynecologist. Like, you know, this isn't. Like, we had a nanny and my mom would, like, say hi to us as we passed in the hallway. Like, Right. There was a need for someone to work at your home.

[C]

For sure. Yeah. And, I mean, I was the sixth child.

[B]

Right. Like, this isn't.

[C]

This is just me, right?

[B]

This isn't the butler.

[C]

Right?

[B]

You know, like, I. For anyone that, you know. No, that's gotta be so annoying. Yeah. We added a nanny. Oh, must have been easy. No, There were like 30 kids.

[C]

Right? Yeah. No, I'm sure. Even. Even with that, it was not right. It was not chill.

[B]

No, no.

[C]

Yes.

[B]

So, I mean, Josephine, she must have been, like, shell shocked.

[C]

Yeah, well, she. She. She's from Mexico and she came and she didn't speak any English, and my oldest brother, like, taught her English and she taught him Spanish.

[B]

Really?

[C]

And they. Yeah, and they.

[B]

And like, they're in love now they have a kid.

[C]

Not quite.

[B]

Oh, okay. Sorry. Sorry.

[C]

Yeah, no, she was my. I think from when I was born until I was. When I was like 8 or 9. Did you have a nanny?

[B]

Wow. I. Yeah, we had. This is a story that's gonna sound weird.

[C]

Let's hear it.

[B]

We had. We had. We never called it a nanny. That was never.

[C]

I mean, I don't know if we called it anything, but, like.

[B]

Yeah, we had women that would, like, be in our house.

[C]

Come and watch you.

[B]

Yeah, come watch. And also clean. And, you know, they were like. So when I was growing up, her name was I. It is so weird to even, like, Odessa.

[C]

Odessa.

[B]

Yeah.

[C]

Okay.

[B]

And Odessa then moved on, did all.

[C]

Of it, the cleaning and watching you.

[B]

Yeah.

[C]

Okay.

[B]

And. But I was very young when Odessa was there. I can't even remember. I can't even believe I remember her name. Then we had.

[C]

You kept in touch.

[B]

No. Then we had Ruth.

[C]

Is she single? I.

[B]

We fell in love, me and Odessa. We had Ruth. Ruth who? Ruth was basically my, like, was like our mom.

[C]

Like, okay.

[B]

In a way. Like, not to give take away credit for my own mom, but Ruth was like a part of our family for a long time. To the point where my brother was, like, in love with Ruth. Like, my brother, like, Actually, actually, or.

[C]

Like, thought she was his mom. Like, act was.

[B]

I don't know. I, I, We've never talked. Have they hooked up? They, they, you know, they enjoyed each other's company. No, I, how old was she? I don't remember. I just remember it was an age where my brother was like a toddler, I think.

[C]

Did you guys compete for her attention?

[B]

Ruth and Harry got along very well. I, I, you're making it sound so much weirder than it was. You're making it. Jordana going into dark personality mode? No, I, no, I, Ruth, I gotta ask her. I haven't talked to him about it in a long time.

[C]

He still keeps up with it. If he told you that they get lunch like once a quarter, would you.

[B]

I would be in shock. No, they don't get lunch once a quarter. That's crazy.

[C]

Once a year?

[B]

No. Ruth, I think, went back to Barbados. She was from Barbados. And I, I've never even asked my parents about it.

[C]

Ruth is not a name I would think would be like, she was the native to Barbados.

[B]

I know, I don't, she was like an amazing person. Like, I, I, I just remember like how calming and amazing she was. And Harry was like, that was like his mom.

[C]

Oh.

[B]

And then after that my grandparents would have, My grandparents used to have.

[C]

Did she live with you, Ruth?

[B]

Yeah, I think, I'm not, maybe, I don't know. My memories, we don't talk about these things. My family, we don't. Like, I feel weird talking about it here. And then my grandparents used to have Asian couples live with them.

[C]

Couples.

[B]

Couples. Because they would be in school, they'd be at like mit.

[C]

Like a foreign exchange student basically.

[B]

And they'd be like at MIT somewhere. Like, like the husband would be like an engineering and I think mostly from China.

[C]

Okay.

[B]

They would come here on like student visas and they were a couple. It was a couple because they would both like, okay, you know, live in the home. They would live in my grandparents house and they'd be. We now, you know, they became part of our family. Sam. Sam.

[C]

You still speak to them.

[B]

Sam and Xiao Ping were like, are like a part of my family.

[C]

Like you still speak to them?

[B]

Of course.

[C]

Oh, you do? Okay.

[B]

I haven't spoken to them in like a few years. But like, like they would be like 20 years.

[C]

But yeah, we still, yeah, well, like.

[B]

If I saw them would be big hugging kisses. Like, Sam and Xiao Ping were like, are our family?

[C]

Were they at your brother's wedding?

[B]

I don't know. I don't think so you're really putting holes into my whole sweet story. Maybe they're sitting at home like people. They didn't invite us to their wedding.

[C]

They were. You said you're just part of the family.

[B]

I would consider that. Well, some of my aunts and uncles.

[C]

Someone's family.

[B]

Well, let me. Let me just also say there's a couple aunts and uncles that didn't go to my brother's wedding either.

[C]

Okay.

[B]

So this happens with families.

[C]

Okay.

[B]

You know, so I. I feel comfortable. So Sam and Shaoing are like, we love them.

[C]

Okay, well, what did.

[B]

I'm sorry we didn't invite you for.

[C]

Your grandparents for like, cook and clean.

[B]

And take care of the house. And then.

[C]

So it's almost like an au pair, but for an older person.

[B]

Right. And then. So then my family started doing it.

[C]

Okay.

[B]

And started having younger Asian couples live, like in the basement.

[C]

Okay.

[B]

So that was always weird to like, people like, wait, there's an Asian couple living.

[C]

We had a foreign exchange student too.

[B]

Yeah, well, we didn't teach them anything. We. This was.

[C]

No, I think they go. They.

[B]

They would go to school.

[C]

You don't teach them someone else.

[B]

Growing up, I'd always have, like, they'd like, like, they'd like make food and I'd have like this, like, amazing, you know, Asian food. Like, I like. We had like spring rolls just sitting in the freezer and I'd like, cook them up when I came home from school.

[C]

That sounds awesome.

[B]

It was great. But.

[C]

And they lived with you?

[D]

Live with us?

[C]

Yeah. My nannies were always living too.

[B]

But not.

[C]

I used to sleep. I used to sleep in the bed with. With them.

[B]

Really?

[C]

Yeah.

[B]

So you're breastfeeding on one side.

[C]

Yes.

[B]

You're sucking on mom's teeth on one side.

[C]

Why do you think I have relationship issues?

[D]

Yes.

[B]

Josephina, it took us eight years to get to this hard hitting episode of the UF podcast with all this information.

[C]

We've been sleeping the bed with my nanny, then go upstairs breastfeed for my.

[B]

Before you had it all. You're like a. A Mormon husband.

[C]

Seriously.

[B]

Just cuddling with one. That's my tit. Yeah. Good for us.

[C]

That's my, you know, actual caring mother.

[B]

Yeah. So, yeah, the nanny thing is like a wild world and it gets so, like, it gets uncomfortable. Like, people make it into this. Like.

[C]

Well, even Mike comes from a family. His mom was a stay at home mom, so he didn't have a nanny.

[B]

So the. This, the idea of this is probably like, what are we doing this is.

[C]

Our biggest, like, cultural difference. I think it's, like, not the religious. When we're different religions. That's not. It's more like he had, like, a stay at home mom who, like, cooked and cleaned his, like, house, and I didn't have any of that.

[B]

And. And now he's. The baby's coming and you're having, like, a night nurse and all that stuff.

[C]

Right. I mean, we've been talking about. It's funny. Like, this is something we've been, like, going through, like, for years. When we first started this, we were on very opposite sides of it. And I think now that, you know, we've been together, like, eight years, it's been. We've come. I think he's understood that times are changed.

[B]

Right. But also. And I'm not.

[C]

I'm not. Obviously not a stay at home mom.

[B]

Yeah, but also. Yeah, that's the thing. Like, it's not like he dated someone who was like, yeah, once we get married, I'm gonna be, you know, doing the Pilates class and.

[C]

Right.

[B]

Staying at home. Like, he kind of knew that.

[C]

Yeah. No, I know. I think it was just. It wasn't even like he was, like, against. I think he was just like, this feels, like, uncomfortable to me.

[B]

Right. It's different. Different is uncomfortable. Yeah.

[C]

Right, so that's funny. That was almost like our big, like, of all the things that was our.

[B]

Listen, he won't be complaining when he's sitting in dreamland.

[C]

This is a man who gets, like, nine and a half hours of sleep every night. I think he'll be fine. It was so funny. We got the cribs. Because we got it. We got two cribs from, like, Pottery Barn. And he's like, I'm gonna put together the cribs. And I'm like, what are you talking about? We're getting White glove delivery service. You're not putting together.

[B]

Why are we changing who we are now? Like, it's like, it's too late.

[C]

Yes. I was like, you can put together, like, the lamp. Right.

[B]

That comes with. That's more. Comes in three parts.

[C]

That's more your speed.

[B]

Yeah, yeah, yeah. Let's. Let's stay who we are. Let's do the show. Let's do it. This is Jordana's last show before we go to maternity leave. We will miss.

[C]

Thank you. I'll be back.

[B]

We'll be waiting for you when you're back.

[C]

I will be back when you. When you least expect it. Or probably around when you expect it.

[B]

Yeah, we will expect it we'll be.

[C]

This show is sponsored by Better Help. There's a lot of pressure in the new year to become some new and improved version of yourself. Maybe for you that means meeting fitness goals, spending less money, cutting back on vices. But we all know change doesn't happen overnight. If you want to make some changes in your life but you aren't sure how to make them, therapy is a great place to start. I love therapy. I've been in it for so many years. It has helped me tackle so many of life's problems and it's helped me make changes slowly and the correct way in the right state of mind and with the help of a licensed professional. I can't recommend therapy enough. If there's anything in your life that where you feel like you're stuck in a rut and you want to make some changes. With over 30,000 fully licensed therapists, BetterHelp is one of the world's largest online therapy platforms. They do the initial matching work for you so you can focus on your therapy goals. A short questionnaire helps identify your needs and preferences, and if you aren't happy with your match, switch to a different therapist at any time. From their tailored recs, BetterHelp makes it easy to get matched online with a qualified therapist. Sign up and get 10 [e-mail] UUP that's BetterHelp. H E L p.com UUP this episode is brought to you by Abercrombie. This year, make Abercrombie denim the core of your capsule wardrobe because denim should feel like this if you want a vintage lived in fit without spending your entire Saturday digging through thrift stores and trying on 37 pairs, Abercrombie's 90s inspired cuts are the answer. Their wide leg jean is the it pair of the season. Lightweight, effortless and elevates any basic outfit. And all of Abercrombie's jeans come in both classic fit and curve. Love the viral fit designed to eliminate the dreaded waist gap. Growth is realizing you don't need to suffer for a good pair of jeans. I love Abercrombie denim. I have probably like four to six pairs of Abercrombie jeans. They're so comfortable, they always look so cute and I just feel like I'm getting a really, really good quality denim outfit at a really, really good price so you really can't go wrong. I'm currently in an Abercrombie sweatshirt, so huge fan of the brand. Love what they're doing in so many different areas. Shop Abercrombie Denim in the app, online and in stores.

[E]

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[D]

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[E]

Ask your doctor about fgliss and visit evglis.lily.com or call 1-800-lilyrx or 1-800-545-5979 if.

[B]

You want to hear more from Jordana who will be popping in on benefits. Go go go go listen to benefits. Go Sign up for it. Five bucks a month gets you two extra podcasts a month ad free day early. All that good stuff.

[C]

So all right, let's do it. Icky or picky?

[B]

Go for it.

[C]

Hi J and J. I'm a new fan but was quickly hooked. 82.

[B]

That's the number that we we really said that forgot about it immediately and people really like it.

[C]

Literally every time someone says it I'm like who is 82 years old listening to the show confuses.

[B]

We should have did a word but now 82 we'll see.

[C]

Too late 82 if I remember it okay and love seeing Jared standup and meeting him backstage in October. Thanks to you both for the thoughtful, funny pod discussions. They are highlights of my week and congratulations on your pregnancy and Jared and killing it in Delray and on your tour. I'm writing in with a petty or prudent for both myself and my ex backstage in October.

[B]

Can we get some more. That makes it sound like I'm like.

[C]

Using one show, right?

[B]

Come on backstage.

[C]

That one time you worked In October, I, 29, female, met my ex, 35, male, at a mutual friend's birthday party and we began a relationship despite living in different cities. He was all in from the start, and I let our lengthy texts and somewhat extravagant visits mask my own doubts about our chemistry and personality fitness. About a year in, and at his encouragement, we decided I'd move to his city to live together, which meant me leaving a job I loved and moving cross country. He was extremely wealthy. I was still getting on my feet. When I moved, he said he wanted to give me $20,000, framing it as a compensation for me giving up my job and selling most of my belongings and to help me feel more independent and less reliant on him for day to day spending. I think phrasing it as compensation is a weird way to phrase it, but.

[B]

Yeah, it's a little weird, right?

[C]

Compens compensation is like the most corporate.

[B]

The moving package will include a $20,000 signing.

[C]

Your signing bonus.

[B]

Yeah, for me, you get $20,000.

[C]

Thoughtful gesture. I was initially hesitant, but I ultimately accepted. Three months later, my doubts about the relationship started to consume me. I was very unhappy. I ended the relationship and moved out of his place. He was furious and we didn't talk for a few weeks until he sent a scathing email about my selfishness, citing particularly that I had not offered to return the money. Wanting to disconnect as quickly as possible, I sent him $5,000, Venmo's daily limit, and offered to pay the rest. He told me not to send any more, and I didn't. When we broke up, I felt the money served its original purpose, preventing me from being beholden to him. Or pulled or pulled to stay in a relationship out of financial need, without a job or significant savings. It meant far more to me than to him, and I didn't feel compelled to return it. Still, I can understand how my keeping it, or at least not offering to return it, might feel wrong from his perspective. So petty or prudent. I kept most of a large sum of money from my. From an ex I broke up with. Would love to hear your take. Signed. And I don't even know how to summarize this batch.

[B]

I like this email because I don't think she knows. Like, like I. I think she's like, I don't know if she knowingly wrote this to make us call him petty.

[C]

Like, I think he's paying for after asking.

[B]

For putting it in the email. Writing an angry email and including in it, hey, I gave you all this money is like, well, it's funny, it.

[C]

Didn'T even sound like he wanted the money back. It sounded like he wanted her to offer the money back as, like, and I'm sorry for breaking up with you thing.

[B]

Or I. I kind of think of it as he wanted to make her feel as bad as he could.

[C]

Right. Well, that was. That's usually what you get when you get a breakup email, Right. When you get, when you get an email, if you've broken up with someone, it's usually like, here are all the things that, like, I'm gonna try to make you feel, like, as horrible about yourself as you possibly can.

[B]

Right. It's like you're running away and they're throwing all the at you as you're running out the door and they're hoping to hit you.

[C]

So, like, and I understand the motive for that. You're like, you feel hurt. Your ego is very bruised.

[B]

Right.

[C]

You kind of like need to villainize the person.

[B]

Especially when someone moves to you and you put them up and you are the one who's established and they're the not established one, and now the not established one is leaving you.

[C]

Right.

[B]

It's an ego hit from the as like, a brand is concerned, like, what people will say, like, his insecurities are. Everyone's going to say, oh, wow, once she got on her feet, she didn't need him anymore, didn't need his money. Now she's running out on him because she doesn't like him anymore. Like, she used him. You know, might be it, especially considering the money angle, the way it's done, it feels very like older guy with money dating younger woman with no money.

[C]

Yeah.

[B]

And he's embarrassed by the idea that, like, she left him.

[C]

Yeah. And that's. That's very clear from, like, him even saying anything about the money back.

[B]

Right. Because the money back. Like, it's petty of him.

[C]

It's petty of him to sit to. I could see. Listen, would it be. Should. Should she have offered to give it back? I don't think she needed to.

[B]

No.

[C]

I don't think she needed to at all. But would it have been if she broke up with him and she felt really bad and said, hey, I know you. Like, I don't know how quickly she. Three months. Three months later she leaves. I could see being like, I know you gave me the money. I really appreciated that. If you want it back, like, I'm Happy to. I'm happy to pay it back. I think that would be like.

[B]

Was it three months?

[C]

Yeah. She said, three months later, my doubts about the relationship started to consume me.

[B]

That.

[C]

So I do think, like, Right. Like, it's not like they lived together for six years and then she left. I could see why he would be like, it would have been nice if you. To, like, offer. So I didn't feel. I wouldn't feel so used.

[B]

Right.

[C]

Because three months. $20,000 in three years. In. In. In three months, if you're a single woman, like, that's like, a good amount of money to be able to spend.

[B]

Right. Well.

[C]

Again, I. I think it's a gift. He shouldn't think of it like that. But I also do think it would have been a. It would have been a nice gesture for her to at least offer. I don't think she should have given it. I don't think he would have. Should have accepted it.

[B]

Right.

[C]

But if I. If someone gave me $20,000 when I moved in with them, I move out three. Three months later. I think I'd say, like, I'm really sorry. I know. Like, you know, we were. It didn't work out. I just don't. You know, whenever you break up with someone, like, you just have to be like, right, you're a little.

[B]

Yeah, right. You're a little bit more in the.

[C]

Position of power if you write. And I would say, like, I'm happy to pay you back the money. I know that was, like, really nice of you, and I think that'd be a nice thing to do.

[B]

No, no, I'm with you. I. As far as. Is it petty that she kept it? Like, at first I was like, I.

[C]

Don'T think it's funny that you kept it.

[B]

No. Because the whole intent of the money was for the move or to try it out.

[C]

Right, right.

[B]

Yeah, right.

[C]

You.

[B]

You volunteer to give me money to make me feel more comfortable in the move right now. The move didn't work.

[C]

She asked for it. Right.

[B]

And it's not like they had a plan for it together. It's not like they were like, and the 20,000 will go towards us doing something. No, that was given to her.

[C]

Right.

[B]

That is for her to move. It was used to move. It was used to make her feel more comfortable. And as she put it, that's her version of the story, but she put it as like. And so I didn't feel beholden to him to stay in a relationship I didn't want to be in. And it's like, yeah, that's your kind of telling of it. I don't really buy that as much.

[C]

Right.

[B]

Like, I don't think he said, take this money so that if you ever fall out of love with me, you can leave without having to be with me. You know, I don't think that was it.

[C]

Right. But I do think again, like, I don't think she should have given the money back. I think even if she, I think she should have offered as like a gesture, it would have been weird if he took it. But I would, I think I would offer.

[B]

Yeah, I would offer even if I.

[C]

Couldn'T do it all right away. I would say. And again, he makes the comment she Venmo's him immediately he's like, don't send. He like, didn't even really want the money. He just wanted her to offer.

[B]

Right. Him saying it is the only real petty thing.

[C]

I agree.

[B]

And then him being like, don't send the rest. I think that's like a nice thing of.

[C]

I don't even think he wanted the. I think once she sent it, he was like, you know, he, he, he only wanted it so he could hold on something to villainize her for.

[B]

Right.

[C]

So once she sent it, that was almost like, it was probably more annoying for him that she sent it because it wasn't about the money. He didn't actually care about the money.

[B]

That's how little she cared about being with him.

[C]

Right.

[B]

She's like, it, take your money. I don't want to suck your dick anymore.

[C]

That's what I'm saying. Like, so that's why he was like, I'm, I'm sure he was like pissed when she sent him the $5,000 watch, which is why he was like, please don't send me any more. This is already like, feels horrible.

[B]

This feels very much older man with younger woman that he was really pumped to be dating.

[C]

Yeah.

[B]

And it seems like she was just like, this is not the life I want. Which is like almost more embarrassing for him.

[C]

Yeah, that's what I'm saying. I do, I do feel like it is, it is a big ego thing. And the letter makes sense. And I could see why he's like grasping at the twenty thousand dollar thing. But it's just something people. When someone breaks up with you, you kind of want to like find ways to make them like an evil piece of.

[B]

Right. And they met at a mutual friend's birthday party, so they know a lot of people in common. So this is like public knowledge to everyone. She Moved across. Oh, my God.

[C]

Right?

[B]

I'm sure there's. There's more publicity here than being acknowledged.

[C]

I'm sure in like a few months, when he gets over this, he will feel embarrassed about what he wrote.

[B]

Right? And he'll find a new woman to give $20,000 to suck his dick.

[C]

Exactly.

[B]

New year, same extra value meals at McDonald's. So now get two snack wraps plus fries and a medium soft drink for just $8 for a limited time only. Prices and participation may vary. Prices may be higher in Hawaii, Alaska and California. And for delivery, let's do some advice. Emails. You ready?

[C]

Yep.

[B]

J and J fan from episode one. Best pot out there. Thank you for never missing a week in eight years. It's a gift to us all. This person gets it.

[C]

They do.

[B]

So when do you know you love someone? Oh, I don't know if we can answer that.

[C]

What's a quick lightning round?

[B]

The minute they give you $20,000. Been dating for a month. We met in the wild. We've had seven dates. Each one has been a marathon from 13 to 21 hours. But who's counting, right?

[C]

13.

[B]

13 to 20. What? What was it? A flight to Australia. Either starting earlier or till late. Till the next afternoon. In this moment, I feel it. Or something like it. Like it's in my head that I love him. When I look. When I'm looking at him. There's also been quite a lot of sex since day two, so I imagine that's clouding my read of the situation. You think? Still, it's extremely easy to spend time with him. Both of us seem kind of shocked about how good and safe it feels. He doesn't text much between dates, though he has called in person. We're both there 100%. Not really on our phones at all. Even given the long ass dates. Neither of us are on the socials either, so that's a match too. He often says I love spending time with you or I love insert thing with or about you. Even after I've said I like doing that same thing. He'll follow it up immediately with the I love dot, dot, dot. A bit of a catch. And I know this is beyond Jordana's comfort level and maybe mine a bit too. Okay, Jordana, Everyone get ready to be uncomfortable. I was not thinking something like this might develop, but he's 24 and I'm 37.

[C]

Pearls to clutch.

[B]

I mean, are you okay?

[C]

I thought she was gonna talk about like some crazy anal, like, like sex situation.

[B]

Before I get into it. I know Jordana won't like it. Jordana, brace yourself, because this news might hit you tough. Why aren't I uncomfortable with it? I. I'm uncomfortable with. I don't think. Right. I. I'm as.

[C]

They must really. I'm like a. I'm like. They're someone's traditional Grandma. Yeah. Yeah.

[B]

24.

[C]

No, this is cool.

[B]

Before I get into it, Jordana, I know you're going to be uncomfortable, but.

[C]

There'S gonna be a big penis flying out of the iPad.

[B]

He's five, seven and a half. Jordan, are you okay? He's 24. I'm 37. Surprisingly, we have a lot in common. Music, movies, family background, hobbies, industry toys. We like video games. He hasn't dated since he was 18, what, a year ago, and. And seems very excited. Making plans, taking me to new places. Oh, he knows. A new playground to play. It the works. I know. Boy Sean was shocked. He said, who's Sean?

[C]

Sean Kilby, I think. Oh, Who's Boy Sean? Is that a new rapper?

[B]

I read. I swear to God, I read this before and I was like. Did she just, like, give the guy a name randomly? No. We're gonna have to call Sean Kilby. Boy Sean.

[C]

Sorry, Sean Ever.

[B]

I'm sorry, Sean. Sometimes a nickname finds you, boy.

[C]

I mean, it has a ring to it.

[B]

It really does. I know. Boy Sean, whose new album is coming out in the fall, was shocked he'd said, I loved you after one and a half months. But I can see it. I just want to make sure I'm feeling it. And I'm also curious about your thoughts on when to say it. We're planning New Year's Eve together, so that could be a fun but also slightly scary time to let it slip, if that's what this is in terms of defining the relationship. We're only seeing each other and he's made that clear. I think I'm in love with him. I. I knew after he goes, hey, we're just chilling.

[C]

Yeah.

[B]

So what say the Jays? Thank you, thank you, thank you. Unexpected and delighted cougar. Well, I'm happy she's having fun.

[C]

Yeah.

[B]

I'm happy that she's been able to get over whatever people would have to get over dating a 24 year old when you're 37.

[C]

I agree. And listen, she's having fun. That's great. If she's into him, that's great. Crazier things have happened. I think that as uncomfortable as this makes me.

[B]

Jordana, I've never seen you so uncomfortable. Seriously, babies, nothing I do. This random woman dating a 24 year old, that's really what made you uncomfortable.

[C]

That's my biggest fear.

[B]

Yeah.

[C]

As you know, as when it comes to children.

[B]

That's true.

[C]

I do think there's a kind of 24 year old guy who really likes the idea of dating an older woman.

[B]

Yeah. There's an adventure.

[C]

Yeah. And is like into that because of those things. I don't know if that means he's more commitment oriented or if it means that he like, likes the idea of like being with a woman of the world. Mm. What are your thoughts on that?

[B]

You know, it's. It's hard with these things. Anything can happen. So let me start on the spectrum of reality. Yeah.

[C]

Any.

[B]

This might be you and him. This is your story.

[C]

You guys could be Demi Moore and Ashton Kutcher.

[B]

This can happen. I don't want to like, yuck her. Yum. She's having fun. She's enjoying herself. I think she should keep doing that. I think if life is to work out together 37 and 24, you're going to have like a different life than maybe you envision. That's okay. This is all to say you have to kind of decide what you want. Like, I don't think like the I love you if you're feeling it and you're enjoying it. I don't know if you can like count on his I love you to be the same as your I love you.

[C]

Meaning. Meaning the same thing.

[B]

Right. Like I, I think like, like at 24, like you love everything. You love everything. You're just having fun. Like, you haven't even thought of your career. Like, I, maybe you're thinking your career, but like, you're just going out. Like when you say you spend 21 hours together, it's because he's got the.

[C]

Time because nothing else to do.

[B]

Right.

[C]

Right. Either this or video games.

[B]

Right. And he's not on social media. But like, I guess, you know, like, it's easy to zone in with one person when you've blocked that time out.

[C]

Right.

[B]

It's way harder to like, do things in your everyday life. Like, you know, hey, I gotta go to the gym this morning. We're gonna go to dinner tonight. You know, start sharing responsibilities. All that stuff is like, in the future. But she's not even asking that. She's like, how do I tell him I love him? Like, I don't even think the, the age matters.

[C]

I think he'll say it back.

[B]

Right.

[C]

Why not?

[B]

And if you're right and I Just think like, you know, I guess if we're.

[C]

I don't know if it means anything.

[B]

Right. I don't know.

[C]

I agree with. You're saying like you. He could, I think likely to say it back. Probably doesn't mean the same thing to him. Wouldn't put much stock in it.

[B]

Right. Like his saying it back. Like, does that mean, like this is the. I mean she does write stuff like that though. Like, so I. She doesn't get to the. He's 24 until the fifth paragraph. He doesn't text much. I mean the fact that he's already made it clear they are nothing. What do you mean she said?

[C]

Well, he says, he said it's clear that we're only seeing each other.

[B]

He's made it clear we're only in ter. We're only seeing each other. He's made that clear. Oh, okay. I thought it. He made it clear that we're only seeing each other. That's what I thought that was like in terms of defining relationship. He's made it clear.

[C]

I read it as like, he's made it clear we're only seeing each other.

[B]

Oh, that's a very different emphasis on the different syllable. Yeah, because I, in my mind I was like, we're only seeing each other. We're only seeing each other.

[C]

Oh, yeah.

[B]

Seeing each other.

[C]

That changes the whole email.

[B]

Right? That's how I read. It's funny how we read it in different ways. If they're only seeing each other and he's made it clear. All right, great.

[C]

They're only seeing each other.

[B]

Right. That version. Then it's like, okay, yeah, you're dating.

[C]

Yeah, that's what I'm saying. I think he love you.

[B]

We're dating and I love you. That's.

[C]

That's it. But I love you again doesn't tell you are my looking for a long term relationship. What is, what do you make of the fact that I'm older than you? Do you feel like you're in this. We're in the same place of life in terms of how quickly we want to move to the next step.

[B]

Right.

[C]

I love you is not answering any of those questions.

[B]

Right. That's. That's the thing we would give you pause on to relate the I love you to. Okay, well maybe we could work out. Maybe we'll go get married. Maybe we'll move in together. I don't think that says anything about that, especially to a 24 year old. I don't think you're jade enough. I don't think you're cynical enough, I don't think you've gone through enough to realize how much those words weigh on someone else. Which he's going to find out once you say I love you and he says it back and then he ends it so that he can go, you know, clubbing in a visa someday. And, and then you'll go, what the. You said I love you.

[C]

And he'll have to learn I did love you.

[B]

That there's consequences for his words.

[C]

Right.

[B]

And I just think that's why we're. That's our advice.

[C]

Yeah. And I think he doesn't realize the.

[B]

Consequences of his words. I, at 24, did not realize what an I love you men as far as future is concerned, especially to a 37 year old.

[C]

Right. And I think that's the part where the age is relevant. Not that, oh, you can't date a 24 year old. It will never work out. It's more like the audience that, that doesn't. The I love the question she's asking is sort of the wrong question.

[B]

2 I love you are not created equal.

[C]

Also true.

[B]

Right. One person's I love you is. Yeah, let's just keep hanging. Another person's I love you is so six months we can move in and a year from then we can get engaged. And then.

[C]

Right.

[B]

You know, I got to have kids because I'm 37. I did get my eggs frozen. And then he's like, that tells you.

[C]

A lot more, right?

[B]

You can get eggs frozen. I thought they were only in the refrigerator section. You're like, no, I'm talking about like having babies. Like, and he wouldn't even know.

[C]

Right.

[B]

So I think the gravity is different for both of you're on planet Earth and he's on.

[C]

And it's, this is the best time for that. Cuz you guys are just both having fun, having a great time again. Nothing wrong with that. But I would just keep that in the back of my head and ask more if you're, if you're worried about asking for something. I would worry about asking for something that's tangible.

[B]

Right.

[C]

Do you want to go away on a trip in a couple months also?

[B]

What do you see the next.

[C]

How much can you contribute?

[B]

You want to go away, Chuck E.

[C]

Cheese, like Disney World.

[B]

Well, also, like, what does the next year entail for you? I have this, this and this going on. Like I, I think at 37 you start to have like these. Like, like my year is planned right now. As, as weird as that sounds.

[C]

No, I minus planned Right.

[B]

As you get older.

[C]

Yes.

[B]

Your plan.

[C]

No. Spontaneous.

[B]

Right. Like. And in his world, he's like, I don't know what I'm doing next week. You know?

[C]

And that could be an abusive.

[B]

Right. As he should fire him. There's plenty of old women there, too. No, I'm kidding. I'm kidding. Okay. We solve dating again.

[C]

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

[B]

I'll be back next week.

[C]

I'll be back on benefits. And then sometime regularly in the near future. I'm not exactly sure when.

[B]

Everybody say, we wish Jordana the best. We're so happy for you.

[C]

I'll miss you guys.

[B]

We'll miss you, too. And you'll be back in no time.

[C]

Yes.

[B]

Holding two babies.

[C]

Yeah, I probably won't bring them.

[B]

Oh, no.

[C]

Should I breastfeed on the show?

[B]

You can do whatever you want.

[C]

Yeah. Right.

[B]

You know, okay. As long as it's okay. I don't know.

[C]

That'll be behind the paywall.

[B]

We'll talk to hr.

[C]

Yes. All right, bye.

[B]

Boom.

[A]

Batches.