Dear Prudence

The “A Hell of a Guy” Edition

My father-in-law was a horrible person. Do we have to lie and speak kindly of him at his funeral? Help!

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Episode Notes

Prudence is joined this week by Josh Gondelman, a comedian who has written for Last Week Tonight With John Oliver and now writes for Desus & Mero. His debut essay collection Nice Try: Stories of Best Intentions and Mixed Results is available now.

Prudie and Gondelman dig into letters about if you should allow guests to speak kindly of your extremely unkind father-in-law at his funeral, how to handle a mother who doesn’t approve of your relationship yet is bossy about your wedding plans, what actions to take when your boyfriend pees in the bed whenever he drinks, what to do when your parents side with a manipulative sister and her bullying boyfriend, how to help your husband tell better anecdotes that don’t turn people off, and whether you owe it to your Jewish community to be “more Jewish,” even though it’s not a big part of your identity.

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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