U Up? Podcast Summary

Episode: “How Do I Navigate My New Polyamorous Relationship?”

Date: November 21, 2025
Host(s): Jordana Abraham & Jared Freid
Guest: Sean Kilby (former producer, current “Picky & Selfish” podcast host)

Brief Overview

This episode of U Up? centers on Sean Kilby’s transition from a 22-year monogamous relationship into the world of polyamory and modern dating. Sean shares candid reflections about ending his long-term partnership, his journey through singlehood and casual dating in his late 30s, and ultimately, entering a non-monogamous—then monogamous—relationship with a new partner. Together with Jordana and Jared, Sean navigates the emotional challenges of finding happiness, negotiating sexual freedom, and the existential questions that shape modern relationships.

Key Discussion Points & Insights

1. Sean’s 22-Year Relationship – The Good & The End

• Details
  • Sean was in a relationship from age 17 to 39 (“22 years, not married” [02:36]).
  • The couple agreed on not getting married or having children.
  • The relationship ended primarily due to a gradual emotional disconnect, accelerated by the pandemic.
  • “We just weren’t connected. We weren’t intimate anymore... and stayed together because this is the person you care about most in the world. This is what a quagmire.” (Sean, [06:26])
  • Post-breakup, Sean experienced relief more than grief: “I mourned it while we were in it.” ([08:23])
• Notable Moment:
  • The breakup was so overdue that during a fight, his partner said, “I can’t wait until we’re broken up,” and he replied, “Me too”—yet it still took another two months ([07:37]).

2. Learning to Be Single in His 40s

• Details
  • Sean had to learn what it meant to be alone for the first time as an adult: “Learning how to be single—right? Like, alone. Learn how to be alone.” ([08:23])
  • He avoided dating apps, choosing to meet people through friends, parties, and in-person events ([12:35]).
• Notable Moment:
  • “My last first date was in an Applebee’s in 12th grade.” (Sean, [12:08])

3. From Monogamy to a “Hoe Phase”

• Details
  • Sean reflected on the connection between sex and love: “I always, always, always strongly associated sex with love... I relate more to women now than I ever have.” ([13:14])
  • He challenged himself to get comfortable with casual sex but found it emotionally taxing: “I wanted to get comfortable with casual sex... it was a journey I wanted to go on.” ([14:42])
  • He admits he led with his history (“Out of a 22-year relationship”—often too soon [13:01]), and found he was “good at the relationship-y stuff, not the flirty stuff” ([16:40]).
• Notable Quotes:
  • “I was raised in captivity. I was a zoo animal... then they let me out into the jungle.” (Sean, [17:54])

4. Starting a Podcast and Embracing Self-Discovery

• Sean launched “Picky & Selfish” with Talia Lickstein to document his “hoe phase” and modern dating experiences ([18:29]).
• The podcast served as both catharsis and accountability as he rebuilt his single identity.

5. Entering Polyamorous & Non-Monogamous Dating

• The Mixer
  • A friend invited him to a non-monogamy singles mixer (“for singles or people who are ethically non-monogamous, polyamorous, whatever” [22:38]).
  • Sean approached this world with intentionality, predicting he “might need to be in an open relationship” to make up for lost time ([24:29]).
• Meeting His Current Partner
  • Met a woman in an established open relationship; chemistry was immediate ([25:42]).
  • “We think the same thoughts all the time. She laughs at all my jokes, I laugh at all her jokes... the chemistry is bizarre.” ([25:42])
  • They quickly became emotionally entangled, even saying “I love you” within weeks ([28:14]).
• Polyamorous Dynamics
  • Sean struggled with being the “other partner” and the logistics of sharing time and emotional space ([29:17], [29:53]).
  • “We clearly already have feelings for each other. I even said to her on our second date, ‘I met you too soon.’” ([27:11])
  • Eventually, the partner left her boyfriend, and Sean and she became monogamous ([32:38]).

6. The Tension of Sexual Freedom and Stability

• Sean misses the excitement and attention of being single, even though he loves his current partner.
• “That version of me that for the first time ever was experiencing freedom, was a happier person.” ([36:23])
• The thrill of novelty and the “risk” of new encounters is contrasted with the stability (and “sameness”) of monogamy ([43:00]).
• “What’s the thing I can’t do right now? Have sex with new people. Honestly... even just flirt for fun.” ([57:15])
• Jared contextualizes: “If you aim for nothing, you hit nothing.” ([47:54])

7. Existential Angst: “What Do I Want?”

• Sean is candid about ongoing anxiety and the feeling of holding himself back: “I want to live with this girl in the apartment I live in now… but I have this feeling in my chest.” ([76:03], [76:53])
• The hosts and Sean explore whether happiness is ever sustainable, or if everyone faces a trade-off between passion and security.
• Jordana suggests, “You do seem to be chasing a little bit of, like, a ghost life.” ([60:58])
• Jared: “You can’t have it all.” ([56:01])

Notable Quotes & Moments

• On Long-Term Relationships:
  • “To me, the most important thing about being in a loving, committed relationship is that you want to be in it actively.” (Sean, [05:17])
• On Polyamory:
  • “Honestly, dating someone with a boyfriend—at first, fine. Kind of nice. It sounds like it would be the best... but the problem is, I fell for her.” (Sean, [28:44]–[29:03])
• On Anxiety & Change:
  • “For the first time in my life since that point where I started being honest about what I want... I’ve experienced anxiety and depression.” (Sean, [33:26])
• On Modern Dating’s Irony:
  • “If you’re a guy who wants to have casual sex and you’re honest that you’re not willing to commit, you’re less likely to get someone to sleep with you.” (Sean, [70:33])
• On Wanting Everything:
  • Jordana: “Is the only way to solve Sean’s problem for his girlfriend to just let him have sex with whoever he wants because he loves her so much?” ([71:37])
  • Sean: “That’s super selfish. Right? That’s not good.” ([71:39])
• On the Limitations & Realities of Relationships:
  • “I don’t think you’re ever going to find the equilibrium… or most people don’t.” (Jared, [60:58])
  • “If you’re looking for a situation that’s going to make you happy 100% of the time, that doesn’t exist.” (Jordana, [75:07])

Timestamps for Important Segments

• Sean describes his 22-year relationship & its end: [02:36] – [08:23]
• Learning to be single, “hoe phase,” and dating anxieties: [12:08] – [18:29]
• Attending polyamorous mixer, meeting new partner: [22:38] – [27:11]
• Navigating emotional fallout of polyamory: [29:03] – [32:38]
• Transition to monogamy & pursuit of happiness: [32:38] – [36:23]
• Tension between sexual freedom and stability: [40:05] – [44:05]; [57:15] – [58:58]
• Existential conversation: “What do I want?” and relationship goals: [59:09] – [76:53]

Tone & Takeaways

The episode is raw, self-aware, and frequently both humorous and soul-searching—true to U Up?'s vibe. Sean’s honesty about his confusion and desires is matched by Jordana and Jared’s friendly but challenging commentary. The discussion hits at the heart of modern dating’s paradox: wanting the thrill of newness and the safety of intimacy, and wondering if anyone can ever have both.

Final Thought:
This episode doesn’t deliver easy answers, but it does offer real talk about the complexities of love, sex, and self-understanding in adulthood.

For more conversations like this, follow @u.up.podcast on Instagram and check out Sean’s podcast “Picky & Selfish.”