Dear Prudence

Dear Prudence: The “Always Testing Me” Edition

My boyfriend is insecure and often makes little comments that are hurtful and annoying. Help!

Listen now:

Listen to the Dear Prudence podcast via Apple PodcastsOvercastSpotifyStitcher, or Google Play.

Prudence is joined this week by Chris Randle, a New York–based writer from Canada who’s written for Hazlitt, the New York Times Magazine, Pitchfork, and Real Life.

Together, they dig into letters about how to handle a brother who is weirded out because he’s dating your ex, how to decide if you should help someone in your friend circle who’s not actually your friend, what to do about a boyfriend who is always testing you and questioning your commitment, how to handle your husband’s teenage cousin who has a crush on you, what actions to take with a husband who monetarily supports his mother and sister instead of contributing to your household, and how to deal with grad school social anxiety and still get some work done.

Slate Plus members will hear Prudie and Randle discuss a letter writer who is wondering how to stop paying a friend’s way whenever they socialize.

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.