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
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.
Key Discussion Points & Insights
1. Jordana’s Maternity Leave and Parenting Fears
(Starts ~04:03)
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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).
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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)
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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.”
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
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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.
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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.”
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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)
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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.
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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)
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)
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
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.”
For More:
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