Prudence is joined this week by Colby Gordon, an English professor at Bryn Mawr College, where he teaches weird gay poems.

Prudie and Gordon tackle letters about what to do when you fear that transitioning would hurt your career, what to consider when your partner leaves you feeling vulnerable about your finances, how to talk to a close friend about her transphobic comments, how to handle regret over not supporting your trans and non-binary friends prior to you coming out as trans, what to consider when you stumble upon your friend’s fanfic Tumblr page.

Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

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Prudence is joined this week by Bijan Stephen, a reporter at The Verge, a music critic at The Nation, and a video game columnist at The Believer. He plays T.K. on the actual play podcast Fun City, hosts a couple shows on Twitch, and his writing has appeared in The New Yorker, The New York Times, Esquire, and elsewhere.

Prudie and Stephen dig into letters about How to come to terms with a long ago relationship you now realize was inappropriate, what to do when your always negative sister-in-law decides to move to your town, how to decide when or if you’ll tell your parents that you’re legally changing your name, what to consider when you feel like you’re competing for your boyfriend’s attention with his female bestie.

 Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

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Prudence takes a look at some of the many memorable letters of 2020 with Grace Lavery, Calvin Kasulke, Toni Golan-Vilella, Lizzy Marmon, Justine D’Souza, and Jack Doyle.

Prudie and company tackle letters about how to decide if you should you let your best friend raise your troubled daughter, what to consider about rewarding weight loss by getting a breast lift, how to handle a husband who gets upset when you mention missing the food from a restaurant that conflicts with your politics, what to do with a mother who only became proud of your job in a grocery in light of the pandemic, and should you report a childhood friend who’s now lying about her upbringing to solicit donations.

Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

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Prudence is joined this week by Harron Walker, an award-winning freelance journalist who lives in Brooklyn. Her work has appeared in GQ, Esquire, and Out, and she is a longtime Jezebel contributor.

Prudie and Walker tackle letters about how to handle a mother-in-law who wants to refer to you as an “aunt” rather than admitting your baby has two moms, what to consider when you suspect your partner is transitioning and is reluctant to talk about it, should you let your parents know before you legally change your name.

 Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

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Prudence is joined this week by Max Jacobs, a radio and podcast producer based in New York. Long ago, he helped produce this show.

Prudie and Jacobs dig into letters about what to do when a neighbor’s cigarette smoke creeps into your apartment, how to cope with your mom’s passive aggressive behavior, what to do when your privileged partner complains about his job, should your wife be more careful about hiding her pot smoking from the kids.

Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected]

Production by Phil Surkis

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Prudence is joined this week by Diana Stegall, the creator of the popular French history podcast, The Land of Desire.

Prudie and Stegall tackle letters about what to consider when bad experiences with therapists leave you wondering if you even know how to “do therapy”, what to do when you realize that your husband is a secret daily smoker, how to handle family who aren’t comfortable that you have the same first name as your partner, should you tell your brother-in-law that your sister is cheating on him.

Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

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Prudence is joined this week by Avery Trufelman, the host of the podcast The Cut, from New York Magazine, as well as Nice Try! a podcast from Curbed about utopian experiments. 

Prudie and Trufelman dig into letters about what to do when you find out that your coworker is engaged to your controlling ex-fiancé, how to handle working in the same industry as a triggering ex-boyfriend, should you feel guilty for drunkenly kissing straight women in college now that you’ve come out as a lesbian, what to consider when you don’t want to spend free time with your husband.

Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

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Prudence is joined this week by Sarah Hagi, a writer based in Toronto, Canada

Prudie and Hagi tackle letters about what to do when your wife gets really upset when you waste any food, what actions to take when you find out that your abusive ex may be harming his new and possibly underage girlfriend, how to connect with a friend who has joined a cult, what to do when an injury ends your sports career, how to stand up to your good friend when they say racist things. 

Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

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Prudence is joined this week by Alicia Harris, a self-described public health nerd based in Oakland, CA. Harris works as a foundation program officer, directing resources to reproductive health, rights and justice organizations.

Prudie and Harris dig into letters where a woman is wondering if it’s okay to cheat if she hasn’t had sex in her marriage for 5 years, what to do when your husband moves out because he hates being a father, but still wants to see you, what to ask your students to call you when you’re trans and still exploring your identity, should you hide your relationship in an area where you are legally below the age of consent.

Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

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Prudence is joined this week by Davey Davis, who writes about culture and sexuality. Their first novel, the earthquake room, is available through TigerBee Press. They write a newsletter about people named David at itsdavid.substack.com. 

Prudie and Davis tackle letters about what to do when your father refuses your attempts at reconciliation, how to steer your family away from triggering you during quarantine, what to consider when sharing your traumatic past with potential partners. Plus, Prudie and Davis respond to a voicemail from a woman who is trying to forgive herself for being in a transactional sex arrangement with someone she now finds repulsive. 

Slate Plus members get an additional mini-episode of Dear Prudence every Friday. Sign up now to listen. 

Email: [email protected] 

Production by Phil Surkis

Learn more about your ad choices. Visit megaphone.fm/adchoices