Dear Prudence

The “To Serve With Love” Edition

My favorite patron at the bar fell off the wagon. I feel so guilty making her drinks. Help!

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Episode Notes

Prudence is joined this week by Peyton Thomas, a freelance journalist and video game writer based in Toronto. His writing has appeared in Vanity Fair, Billboard, and Pitchfork.

Prudie and Thomas dig into letters about how to handle feeling not nonbinary enough for your trans boyfriend, what to do when your friend in recovery comes to your bar and orders a drink, what actions to take if you feel your fiancée has befriended a con artist, what to do when your partner’s lack of direction feels like it’s holding your own future plans back, and how to let a new friend know that even though you declined a last-minute hiking invite you still want to be friends.

Access all of Prudie’s podcasts and columns here.

Got a question for Prudie? Send it to or leave a voicemail message at 401-371-DEAR (3327), and you may hear your question answered on a future episode of the show.

Production by Phil Surkis.

About the Show

Whether it’s a challenge with a lover, a fight with a difficult roommate or boss, or you just like to hear about the challenges other people face, Dear Prudence is the podcast for you. Every week, Prudie and special guests answer questions about relationships, sex, work, family, and life.

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