Prudence is joined this week by Michelle Dean, a writer based in Los Angeles. Dean is the author of Sharp: The Women Who Made an Art of Having an Opinion, and the co-creator of Hulu’s Emmy­- and Golden Globe­–winning The Act.

Prudie and Dean tackle letters about what to consider when you want to pursue a polyamorous relationship with your boyfriend and your best friend, what to do when your propensity for making fun of people has left you with no friends, how to navigate a relationship with your partner while also having sexual conversations online with men, and what actions to take when a manager at your job refers to himself as your “master.”

Access all of Prudie’s podcasts and columns here.

Got a question for Prudie? Send it to prudence@slate.com 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.