Live from the Oregon Country Fair with Reggie Watts

·51 min·5 clips

Sophie, a fair regular, closes her eyes as three bachelors line up behind her for a live dating game.

The episode opens with Natasha Leggero and Moshe Kasher introducing their podcast and promoting their secrets hotline and email for advice seekers. They welcome the audience live from the Oregon Country Fair and introduce guest Reggie Watts, who describes the fair as a gathering of arts and crafts in the forest. The hosts read written-in questions from listeners, including one about a situationship where a man wants to keep things casual but sleeps over often, with Reggie humorously suggesting he might love the apartment more than the person. Another question involves a date who hasn't touched below the waist after eight dates, prompting discussion about asexuality and communication. The hosts then bring up Bennett and Irie from the audience for live advice; they reveal they both work at Burning Man and have known Moshe for years, living on his property for nine years. Bennett and Irie ask how to manage conflict in stressful work environments while keeping the magic alive in their relationship. Natasha shares their rule from filming Another Period to not discuss work after leaving the set gate, emphasizing boundaries. Moshe adds that protecting each other's solitude is key, sharing a story about a man on a plane who said that's the most important thing in a relationship. Reggie chimes in about the importance of listening and being honest about comfort levels. The episode shifts to a live dating game segment with bachelorette Sophie, who has attended the fair six times and works in the service industry. Sophie asks the three bachelors—Ryan (Remy), Toe Jam (TJ), and Anthony—questions like what they get the most compliments on and their worst jobs, with humorous and sincere answers. After the questioning, Sophie chooses Anthony, and the hosts offer to pay for their meal at the fair. The episode concludes with a secret from a caller who hit a pedestrian with their Prius and never told their partner, followed by farewells and promotions for Reggie's show.

As heard by us

A loose festival-floor advice episode where protecting solitude somehow ends at surfing.

The Oregon Country Fair gives this live Endless Honeymoon episode an easy frame for parenting jokes, relationship advice, and festival oddities to sit side by side.

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Why you'd press play

Press play for a live Oregon Country Fair hang with relationship advice, parenting-side-eye, and a surfing answer that somehow becomes the takeaway.

Read the full recommendation in PlayNext →

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