U Up? Podcast Summary

Episode: Should You Break Up Over Bad Kissing?
Date: February 27, 2026
Hosts: Jared Freid (comedian) & Jack Maloney (guest host)
Main Theme: Navigating modern dating dilemmas—primarily, whether “bad kissing” is a valid reason to end a promising dating situation. Also, broader issues around intimacy, vulnerability, perception in relationships, and advice for underrepresented daters.

Episode Overview

In this engaging, candid episode of the “U Up?” podcast, with Jack Maloney stepping in during Jordana Abraham’s maternity leave, Jared and Jack explore a listener’s question: Should bad kissing be a dealbreaker after a string of otherwise promising dates? The duo offers humorous anecdotes, emotional insights, and direct feedback, also branching into deeper questions around attraction, intimacy, queer dating experiences, and inclusion. They tackle three main listener situations: “bad kisser—ick or picky?”, the social fallout of breakups, and dating as a trans woman.

Key Discussion Points & Insights

1. Catching Up with Jack: Dual Approaches to Dating

[02:05–04:53]

• Jack shares his current approach: “I kind of have a dichotomy in my dating life…one half of me is really dating with intention, like I’m looking for a boyfriend, and another half of me that’s kind of just slutting it up.”
• The conversation highlights the tension between wanting serious connection and casual exploration—a pattern they agree transcends sexuality or gender identity.
• Jared: “A lot of women get frustrated with men…because there is this, like, devil and angel thing going on constantly.”
• Jack reflects empathetically: “Girls, looking at you as a gay man, I can completely empathize…as a man, I know how we think too. I know I’m capable of the same evil.”
• They discuss how this “dual track” is common and not about being “evil”; it’s intrinsic to human nature, regardless of sexuality.

2. Icky or Picky: Bad Kissing as a Dealbreaker?

[05:49–19:02]

Listener Dilemma

• A listener reconnects with a guy; great first date with chemistry, but second date includes “aggressive, stiff, too-plentiful tongue” and a “breast exam”-like second base.
• She asks: Is it fair to dump someone over bad kissing? Or can/should it be fixed?

Hosts’ Perspectives & Anecdotes

• Jack’s Experience: Shares about an ex who was attractive but “kissing him felt like kissing a wall…lips closed, no tongue at all.”
  • “I would literally try to actually aim my tongue into his mouth to be like, you gotta open up, bro.” [11:25]
• Head and Heart Analogy:
  • Advice from Jack’s mom: “Relationships and dating are all about head and heart connection…You want to be with someone who your head and heart are in agreement with. Head being emotions…Heart is more passion, sex, like physical chemistry. It’s half of the equation.” [11:45]
  • The listener has the “head” connection but not the “heart.”

How to Handle “Bad Kissing”

• Give it another chance if the dates are good; context matters—the setting may impact kissing quality.
• Jared: The first or second makeout could happen “on a street corner, car, restaurant door…not the best venue for a kiss.” [13:53]
• Suggests using gentle, in-the-moment feedback: “I need them to respond positively to me saying, ‘Slow down.’” [15:43]
  • “Slow down is not negative…It does help people reassess their timing.” If someone responds well, it’s hopeful; if they don’t, it’s a red flag.

Notable advice:

• “Slow down” is presented as a diplomatic, non-shaming corrective.
• Emphasize positive reinforcement—“direct cinematically,” keep things sexy, compliment even small good things.

Dealbreaker Verdict

• It’s ‘picky’ to walk after one bad kiss if everything else is strong, but if they can’t respond to gentle direction or feedback, the ‘ick’ is valid. [18:51]
• Try changing the venue/context for next intimacy.
• “Give it one more chance and see how they respond to a ‘slow down’ in the moment.” [19:03]

3. Breakup Fallout: When the Dumper Gets the Villain Edit

[21:32–27:03]

Listener Situation

A listener broke up with her BF shortly after he lost his job; he’s now spreading that she “only wanted him for his money.”

Jared’s Insight (Solo segment)

• “The consequences of ending something with someone is that they have a story that people will agree with more than you…That’s the consequence. You ended something for no reason at all. You had a good person that liked you, and you were like, ‘eh, I’m out.’…Your story’s not juicy…His story—‘I lost my job, she left, must’ve been for money’—is juicy.” [22:52]
• If you are “the dumper,” some people will always see you as the villain.
• Don’t “meet petty with petty”—react with calm truth. One text is enough:
  • “Hey, some things got back to me that made me feel really badly…I want you to know that if it came off that way, I’m really sorry you felt that was why I was with you. That is not the truth.” [25:13]
• Accept others’ perceptions as outside your control.

4. Dating as a Trans Woman: When Inclusion Doesn’t Extend to Romance

[27:56–42:35]

Listener’s Email

A 24-year-old trans woman shares her pain: friends affirm her identity with pronouns/names, but never consider her “a real option” for straight male friends. She worries about being invisible or written off before being given a chance.

Candid Conversation

• Both hosts reflect on being “othered”—not the default choice in dating situations (Jared as the “funny” or “overweight” friend; Jack discusses being othered in the gay community for body type).
• They clarify: While being “othered” is a universal pain, being trans presents unique and compounded barriers—lack of options, cultural judgment, gatekeeping based on transition status.
• Jack: “Your friends see you as a woman until it becomes about sex and dating…they affirm you socially but not romantically.” [35:49]
• Jared: “Using the right terms doesn’t mean that they see you as the way you want to be seen… This happens to everyone who feels othered.” [31:20]
• The problem is with the friends—not the men. Jack urges calling out friends (gently): “Hey, maybe you didn’t mean to, but it hurt when you didn’t treat me as a real dating option.”
• Both discuss social stigma and the additional hurdle for men dating trans women—fear of judgment, rethinking sexuality, insecurity about identity.
• Jack: “If you know that your anxiety or fear of maybe endeavoring with a trans woman comes from society, then maybe challenge yourself to push past it.” [41:24]
• They acknowledge: societal and internalized biases make this challenging, but progress comes from actual inclusion, conversation, and (over time) more public positive models.
• Name-drop: Jim Norton, a comedian married to a trans woman, would be a great future guest for insight.

Memorable Quotes

• “Relationships and dating are all about head and heart connection…It’s not all head, all heart. You need a little bit of both.” – Jack Maloney [11:45]
• “Slow down is just such a great way of giving a review that’s not shaming them, but parenting.” – Jared Freid [16:44]
• “Meeting petty with petty will only get you more petty. Throwing gasoline at a fire will only make more fire.” – Jared Freid [25:14]
• “Your friends see you as a woman—until it becomes about sex and dating.” – Jack Maloney [35:49]
• “If you know that your anxiety, your fear of maybe endeavoring a trans woman, comes from society, then challenge yourself to push past it.” – Jack Maloney [41:24]

Notable and Lighthearted Moments

• Otter jokes: Jared jokes about “otters only” and posting otters in hats for laughs. [01:46, 08:51]
• Candid discussion about porn as early sex ed: “We had SeanCody.com…like a fraternity naked. That’s what it feels like.” – Jack [08:20]
• Classic comedic banter: comparing bad kissing to “a medical professional looking for romance, not a medical exam.” [07:12]
• Reflection on “the plight of the straight man” regarding stigma about enjoying sexual experimentation [37:31–39:13]

Timestamps for Key Segments

• [02:05] – Jack’s “dating dichotomy”—intentional vs. casual dating life
• [05:49] – “Icky or picky” listener email: Bad kissing dilemma
• [11:11] – Jack’s personal “bad kisser” story; “head and heart” theory
• [13:53] – Context matters: why bad kissing on early dates may not count
• [15:43] – “Slow down” as effective, non-shaming feedback
• [18:51] – The dealbreaker verdict: ‘picky’ for one time, ‘ick’ if consistent
• [21:32] – Listener voicemail: Breakup after job loss, villain edit
• [25:13] – Exactly how to send a “dumper” text for clarity
• [27:56] – Listener email: Being a trans woman not considered a real dating option
• [31:19] – Jared: The difference between social affirmation and romantic inclusion
• [35:49] – Jack: “Friends see you as a woman until it comes to sex and dating”
• [41:24] – Jack: On challenging social anxieties and dismantling stigma

Final Takeaways

• Bad kissing is not an immediate dealbreaker—context, feedback, and a second chance can often resolve the “ick.” However, inability to adapt or respond to feedback is a valid dealbreaker.
• Social affirmation doesn’t always equal real inclusion or romantic possibility. Open conversations with friends (and ourselves) are critical to moving forward.
• Cultural messaging and stigma (around men’s sexuality and trans inclusion) complicate dating, but challenging these narratives—both in ourselves and our circles—is key.
• The hosts maintain a candid, warm, and funny tone while addressing vulnerable, real-life dating experiences.

For full stories, relatable laughs, and more advice, follow the U Up? podcast on Instagram @u.up.podcast or subscribe for bonus content.