U Up? How Do I Navigate My New Polyamorous Relationship?
Nov 21, 2025
Sean Kilby, a former producer of the show and recently single after a 22-year relationship, shares his journey into casual dating and navigating non-monogamy. He discusses the thrill of speed-dating and his intense connection with a woman in an open relationship. As they explore their dynamics, Sean grapples with the balance between love and casual encounters. He reflects on his desire for exclusivity and the happiness found in both single life and committed relationships. The conversation dives into emotional work, FOMO, and the tension between stability and freedom.
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Breaking Free After 22 Years
- Sean left a 22-year relationship and immediately struggled to learn how to date and be alone.
- He speed-ran dating, joined mixers, and treated casual sex as a learning curve to gain experience.
Sex And Love Were Entangled
- Sean realized he strongly associated sex with love and lacked casual-sex experience.
- That gap made casual dating emotionally harder despite his emotional maturity.
Protect Hearts When Dating Casually
- Don't be reckless with anyone's heart when exploring casual sex.
- Communicate boundaries clearly to avoid unintentionally leading people on.