Dear Prudence

Dear Prudence: The “Shy Spy” Edition

I have a top-secret job that I can’t talk about. How do I not scare off dates? Help!

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

Prudence is joined this week by Hillary Eason and her brother, Tyler Eason. Hillary works in international development in Washington, and Tyler is a data engineer in the Bay Area. They claim to have another sibling who is arguably better at giving advice, but she was not available.

Together, they tackle letters about accepting a dream job that you’re not allowed to talk about with anyone, whether should you tell your grieving parents that your sister was pregnant when she died in a car accident, what to do when you’ve only had crushes but now wish to enter the world of dating, what to consider when your daughter wants you to financially support her through her unplanned pregnancy, how to handle a woman demanding to know if she is the daughter of your deceased husband, and what actions to take to mend an old broken friendship in light of your kids being in preschool together.

Slate Plus members will hear Prudie, Hillary, and Tyler discuss a letter writer wondering what to do about his wife when she gets upset over his attempts to make plans to see friends or family.

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 Phil Surkis.