Big Mood, Little Mood

The “He Could Be the One” Edition

My sister is dating a felon. She says I’m being judgmental, but I don’t want him around my house or daughter. Help!


Episode Notes

Prudence is joined this week by Kaitlyn Greenidge, the author of the novel We Love You, Charlie Freeman. Greenidge has written for the New York Times, the Wall Street Journal, Vogue, Glamour, Elle, Virginia Quarterly Review, and other places.

Prudie and Greenidge tackle letters about what to do when your sister is dating a felon who’s fighting a heroin addiction, what to consider when you find out that your boyfriend fathered a child that he wants nothing to do with, whether you are obligated to return your boyfriend’s meat cleaver after finding it a year after you broke up, how to politely ask friends to return books you consider long overdue, and whether you should discourage your not-very-sensitive boyfriend from becoming a therapist.

Join us for a live Dear Prudence at The Bell House in Brooklyn on Thursday, April 23rd at 7:30 p.m. Get your tickets now!

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

Every week, Danny M. Lavery brings on a guest to answer questions from listeners before diving into conversation about relationships, dissatisfaction, drives, regrets, estrangement, embarrassment, self-assessments, and feelings from the monumental to the minute.

Submit your questions to Danny about manners, morals, and more here.

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