Dear Prudence

Dear Prudence: The “Crush On My Job Interviewer” Edition

Is it inappropriate to ask out someone who could be my future boss? Help!

Prudence is joined this week by Courtney C.W. Guerra, an editor and writer who’s been giving advice as Businesslady since 2014. Together, they tackle questions about talking to a partner who thinks they know how to do your job better than you, how do decide if you’re ready for a big move to a new job, what obligations you have to answer work texts when your job provides your phone, how to talk to your parent about not wanting their new partner to officiate your wedding, and if there is an appropriate way to see if a job interviewer felt the same sparks you did.

Slate Plus members will hear Prudie and Courtney discuss an additional letter about weighing your options when you want to hire a close friend to work for you.

Listen now:

Access to the full Dear Prudence podcast is available exclusively to Slate Plus members. Learn more and listen to previous episodes at

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.

Read Prudie’s Slate columns here. Production by Max Jacobs.