Episode Overview

Podcast: U Up?
Hosts: Jordana Abraham & Jared Freid
Episode: I Can’t Stop Comparing Myself to His Ex!
Date: January 28, 2026

This episode dives into a mix of dating dilemmas, relationship dynamics, and personal updates from Jordana and Jared, with their signature humor and honest takes. Highlights include an exploration of dating someone with kids and a difficult ex, navigating death and grief in new relationships, and evaluating whether certain partner behaviors are “icky” or just picky. The hosts also connect their personal lives to broader dating themes, blending anecdotes, listener emails, and honest advice.

Key Discussion Points & Insights

Life Changes and Relating to Dating

Timestamps: 00:41–05:28

• Jordana’s pregnancy and maternity leave: Open conversation about Jordana's anxiety around leaving the show for maternity, her friendship with Jared, and their ongoing podcast relationship.
• Comparisons to dating life and new beginnings: Jordana likens the unpredictability of childbirth to entering a new relationship: "Like, you're single... you have no idea what your wife is going to be like. I have no idea what these kids are going to be like." (Jordana, 01:56)
• Jared’s perspective on fatherhood (even as a friend): He discusses his “Funkle” status (“all the fun, none of the stress”) and relates it to impersonal relationship advice.

Sports, Fandom, and Compatibility

Timestamps: 05:28–10:16

• The hosts banter on college mascots, irrational sports fandom, and how it can impact relationships.
• On sports compatibility:
  • “I don’t like irrational sports fans. ... Some couples, that's their thing together, which I think is a beautiful thing.” (Jared, 07:37)
  • They discuss how their tastes in sports would mesh (or not) with potential partners.

AI, Chatbots, and Emotional Support

Timestamps: 10:16–14:43

• Jordana’s pregnancy pains → ChatGPT as a confidante: She shares using AI for advice/support, noting, “ChatGPT is like, feels like your friend. Like, they'll talk to you. Like, really nice.” (Jordana, 11:37)
• Raises questions about tech’s increasing role in emotional life: Jared jokes about AI romances mirroring the movie Her.

Celebrity Dating & Image Perceptions

Timestamps: 14:43–21:22

• The hosts digress into celebrity dating histories (Scarlett Johansson, Ryan Reynolds, Ben Affleck, Jennifer Lopez) and “Q ratings” (public personas).
• Memorable moment: Jared describes meeting Scarlett Johansson: “You get in front of her and you're like, oh, you're like the size of a woman I've dated. ... On the screen, she's... so different than how I view her as a human.” (Jared, 14:13–15:03)

Listener Email 1: ENM, Field App, and Dating Expectations

Timestamps: 25:06–33:13

Scenario

A listener writes in about an awkward Field app date setup: when planning to meet, her date bluntly insists, “I have kids at home, so either you would host or we can get a hotel room. Let me know if that works. Thanks.” She was hoping for drinks/a normal intro.

Insights & Advice

• On language/code: Both agree nothing about asking for a “location” implies a hookup. “On Hinge, if someone said, do you have a location in mind... that would be insane.” (Jared, 29:01)
• Difference in ENM approaches: The hosts stress that even within open relationships, not everyone aligns: “The ENM to him is different than ENM to you. Not everyone’s here for the same reason.” (Jared, 30:32)
• Boundary-setting praised: They support the listener’s respectful boundary: “You do you, I'm gonna do me. I'm out.” (Jared, 32:38)

Ick or Picky: Loogies & Snot Rockets in Public

Timestamps: 34:11–45:41

Scenario

A woman is grossed out by her long-term boyfriend’s public snot rockets/loogie-hawking while walking the dog.

Takeaways

• The hosts discuss whether this is “normal guy behavior” or genuinely off-putting.
• “I feel turned off when you do this.” Jared suggests clear, emotion-focused communication instead of joking complaints.
• On desensitization: “Men do believe you want to f*** us until the day you die... Women are a fickle bunch.” (Jared, 44:24)
• Conclusion: They're sympathetic—being grossed out is valid, and if it’s turning her off, it’s a fair issue to raise.

Navigating Grief While Dating

Timestamps: 45:42–51:26

Scenario

A listener who recently lost her brother wonders how and when to bring up this grief in the dating process.

Insights

• Both emphasize not everyone deserves (or needs) that info up front: “People have to earn information from you.” (Jared, 47:44)
• Timing for sharing should depend on her comfort and the connection—not a rule.
• Jordana: “If that happens and the person's like 'this is a lot for me', they might not be right for you right now.” (48:39)
• Both are adamant: having a real, emotional conversation isn’t a turn-off to a worthy partner.

Red Flag or Deal Breaker: Dating Someone with Kids and a Difficult Ex

Timestamps: 52:41–60:13

Scenario

A 32-year-old woman is dating a 37-year-old man with a 6-year-old daughter and a “difficult” ex-wife. She questions if his history is a red flag or just part of dating at her age.

Discussion

• Jared notes on mindset: “She’s not all in.” He encourages examining her lack of enthusiasm and scarcity mindset: “Our words are spells.”
• Jordana points out: It's okay if she decides being a stepmom isn't her preference.
• A memorable (and awkward) listener line: “PS the ex-wife is hot and the daughter is already absolutely stunning. I suppose a silver lining.” Both hosts call out the weirdness, highlighting the focus should be on love and connection, not superficial ‘silver linings.’

Red Flag or Deal Breaker: Table Manners

Timestamps: 60:16–63:10

Scenario

Listener asks if licking a plate/bowl, or drinking soup directly from the bowl on a date, is a red flag or deal breaker.

Insights

• Hosts agree early on, it’s a deal breaker, but further into a relationship, small quirks like this are less serious.
• Picking up food from the floor is less offensive (“the 2 second rule is a thing”).

Red Flag or Deal Breaker: Serial Short-Term Dater

Timestamps: 63:11–69:35

Scenario

A listener starts dating a guy whose relationships never last longer than 6 months. Is his track record a red flag?

Takeaways

• Jared identifies: “This is me... It’s going to take a lot for me personally and for this relationship, this match, to like push me into a certain amount of delusion that the next step is possible.” (Jared, 65:20)
• Jordana and Jared agree: Past performance isn’t always predictive, but it’s the only data you have—so take it seriously, but don’t assume it’s destiny.
• The real key: communicate about expectations and check in, rather than assuming history will repeat.

Notable Quotes & Memorable Moments

• “Do you think that because I don't know you yet.” (Jordana, 20:36) — on listeners who say they’d be friends with the hosts.
• “The ENM to him is different than ENM to you. Not everyone’s here for the same reason.” (Jared, 30:32).
• “Men do believe you want to f*** us until the day you die... Women are a fickle bunch.” (Jared, 44:24).
• “People have to earn information from you.” (Jared, 47:44).
• “Our words are spells.” (Jared, 55:15).
• “I'm not going to stop the wedding...I'm as skeptical of closed relationships as I am open relationships.” (Jared, 32:25).
• “This is me.” (Jared, 65:20) — honesty about his own dating patterns.

Episode Flow

• Catch-up and personal updates (Jordana’s maternity, banter about sports and life transitions)
• Celebrity talk and “Q rating” game
• Listener emails: Featuring themes of ENM, boundaries, dating etiquette, loss, blending families, and partner quirks
• Recurring Red Flag/Deal Breaker Games: Table manners, dating resumes, relationship “ick”
• Closing thoughts—value of honesty, self-awareness, and not being afraid of tough conversations in dating

For more dating insights—and plenty of laughter—follow @u.up.podcast and tune in for new episodes!