U Up? Podcast Summary
Episode: Is He Avoiding Sex On Purpose? ft Dr. Naomi
Release Date: March 6, 2026
Hosts: Jared Freid (in for Jordana Abraham, on maternity leave)
Special Guest: Dr. Naomi Bernstein, therapist and co-host of Oversharing
Main Theme
This lively, nuanced episode explores issues of emotional readiness for sex in new relationships—particularly when one partner has baggage, like a recent divorce. Jared and Dr. Naomi examine listener dilemmas around intimacy timelines, what “not my type” really means for dating, and how to tell the difference between being “too nice” and being the right kind of nice. The episode also emphasizes tradeoffs in long-term relationships and the importance of mindset when navigating dating and life transitions.
Key Discussion Points & Insights
1. Transitioning Podcast Duties & Parenthood Realness
[00:02–03:32]
- Jared welcomes Dr. Naomi as co-host during Jordana's maternity leave.
- The two acknowledge the supportive community around new parents, sharing relatable anecdotes about dads adapting awkwardly to newborns.
- “Newborns and dads…they take some time, I think, most of the time to settle in. But he'll get there.” – Naomi [01:48]
- Lighthearted banter sets an open, honest tone for the deeper relationship discussions to come.
2. Therapy Trends & Common Struggles Among Millennial Daters
[05:55–08:04]
- Jared asks Naomi: “What’s kind of in right now?” in therapy.
- Top issues Naomi is seeing:
- Life timeline anxiety (“Is this it?”)
- Work unhappiness/midlife transitions
- The challenge of seeking fulfillment versus accepting current circumstances
- Dr. Naomi extols the value of group therapy, citing how it exposes people to diverse perspectives and struggles, leading to compassion and normalization.
3. Trade-Offs and Mindset in Long-Term Relationships
[14:18–18:49]
- Quote of the day: “When the pain of the pain is greater than the pain of the change, you change” (Dr. Naomi, [14:18])
- Naomi explains this addiction-recovery concept applies to dating: Change happens when staying the same becomes more painful than risking something new—whether that’s leaving a job, partner, or way of thinking.
- The panel stresses that “you can’t have it all,” and happiness comes from positive trade-offs and mindset shifts rather than waiting for perfection.
- “If you're physically attracted to someone, they're a little bit less annoying...” – Naomi [17:17]
- Jared praises Naomi’s marriage: “Let me just say, some sexual tension between you and your husband. There's a palpable…” [16:48]
4. "Not My Type"—Valid Reason or Self-Sabotage?
[18:49–24:41]
- Jared shares being set up often and feeling judged when he passes on potential dates, saying “not my type.”
- Naomi explores gender differences:
- For men, “not my type” often signals a lack of sexual chemistry
- For women, it can mean general lack of attraction, but is less likely to ruin a relationship long-term if other elements are positive.
- The two reflect on how “having a type” is nuanced, deeply personal, and not always externally logical.
- Jared: “The way I sweat for someone, right, is different…the chemical, physical, animalistic, you know, drool. It's for a different type.” [24:23]
5. Ick or Picky? Email Segment—Is He Avoiding Sex On Purpose?
[30:27–37:13]
- Listener (34F) dilemma: Dating a recently divorced man (37) who is emotionally and physically slow to deepen intimacy. Is this a red flag or just her being picky?
- Naomi’s take: It’s normal for someone post-divorce to move slowly—especially a sensitive guy dating someone new for the first time in years.
- Jared role-plays as the hesitant man, exposing deeper reasons (fear of hurting someone else again, guilt, equating sex to a commitment).
- “Every time I get close with someone, I feel like the sex would lock me in...That’s why I’m pushing off.” – Jared as fictional guy [33:39]
- Naomi suggests a gentle, clear conversation can help both parties.
- “There’s a fallacy that someone needs to be perfectly healed before they move on…You can do that with someone, as long as you’re communicating about it.” – Naomi [37:07]
- Takeaway: If you feel more “icked out” by the context after hearing this, it’s okay to leave; but if you feel empathetic and patient, stick with it.
6. Ick or Picky: "Too Nice For a Casual Date?"
[39:28–47:37]
- Listener (30M): After a positive but “nice guy” first date, a woman (31) says he’s “too nice for a casual date” and suggests being friends.
- Series of texts reveal earnest, polite messages but no chemistry.
- Naomi’s analysis: For casual dating, some women seek more assertive or sexually charged partners—not necessarily “nice guys.” The “nice guy” might be excellent long-term, just not for a fling:
- “For a short-term casual sexual thing, I think she’s looking for a little bit more of an assertive alpha type.” [43:29]
- Jared likens dating apps to “stud fishing,” creating mismatches between projected personas and actual desires:
- “This is less, you know, catfishing. This is stud fishing. He acted a certain way on the app...and she's like—where's The Rock?” [45:39]
- Takeaway: Right person, wrong time and context—the “too nice” guy will be perfect for someone ready for a relationship, just not for someone seeking casual fun.
Notable Quotes & Moments
- [14:18] Naomi: “When the pain of the pain is greater than the pain of the change, you change.”
- [16:48] Jared (on Naomi's marriage): “There’s fun energy. A little bit of ball busting…palpable sexual tension…How do you do that?”
- [20:14] Jared: “Look at my for you page—it’s a bunch of big tittied models...stop sending the skinny blondes.”
- [33:39] Jared (role-playing hesitant guy): “Every time I get close with someone, I feel like the sex would lock me in...That’s why I’m pushing off.”
- [37:07] Naomi: “There’s a fallacy that someone needs to be perfectly healed before they move on…You can do that with someone, as long as you’re communicating about it.”
- [43:29] Naomi: “For a long term partner, a beta is great...But for a short-term casual sexual thing, she's probably looking for an assertive alpha type.”
- [45:39] Jared: “This is less…catfishing. This is stud fishing. He acted a certain way on the app…”
Key Timestamps
- 00:02–03:32 – Parenthood and taking over for Jordana
- 05:55–08:04 – What’s trending in therapy today
- 14:18–16:42 – “Pain of the pain” and embracing tradeoffs
- 18:49–24:41 – Real talk: “not my type” and attraction, gender
- 30:27–37:13 – First major Ick or Picky scenario: fear of sex after divorce
- 39:28–47:37 – Second Ick or Picky: getting rejected for being “too nice”
Tone & Atmosphere
- Candid, funny, warm; frequent confessions and real-life examples
- Dr. Naomi provides calm, analytical insight; Jared delivers wit and relatability.
- Encouraging, with highlights on self-awareness, honest communication, and embracing personal quirks—even when they’re “too much.”
Final Word
Whether you’re someone wrestling with emotional readiness, frustrated when “not my type” gets questioned, or just tired of being “the nice guy,” this episode delivers validation, practical insight, and plenty of laughter. The ultimate message: Be honest about what you want, accept the tradeoffs, and communicate directly—because you’re not alone, and there’s a right-fit relationship (or casual fling) waiting for you if you stay true to yourself.