Dear Prudence

Dear Prudence: The “Feeling Guilty” Edition

My oldest friend has been cheating on his girlfriend, whom I know and respect. Do I say anything? Help!

Listen now:

Listen to the Dear Prudence podcast via Apple Podcasts, Overcast, Spotify, Stitcher, or Google Play.

This week finds Dear Prudence live on stage at the Brava Theater Center in San Francisco. Recorded on March 7, Prudie was joined onstage by New York Times best-selling author Jasmine Guillory. Guillory’s books include The Wedding Date, The Proposal, and the forthcoming The Wedding Party.

Together, they dig into letters about how to handle your bestie’s new friends, who leave you feeling alienated; whether you should date your neighbor even though it might be confusing for your children; what to do when your longtime friend is a cheater and it’s awkward to face his girlfriend; what actions to take when your expensive grad school degree hasn’t yielded any job prospects; what to do when two crucial members of your wedding party are going through an ugly divorce; how to handle a husband who wants to maintain a relationship with his white supremacist brother; and whether you see your estranged parents after years of conflict.


Slate Plus members will hear Prudie and Guillory discuss a letter writer who is wondering what actions to take when you find out your boyfriend has known about your affair for months but has been silent, as well as questions from the live audience!

The full Dear Prudence podcast is available exclusively to Slate Plus members. 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.