First up: an exciting update on the one true way to date a former boss and how Prudie helped make it happen. Then, your letters! My mom wants me to discourage my daughter from doing “boy” things. My friends are convinced my boyfriend is a stalker! My boyfriend has bad table manners and I’m worried it’s going to have professional consequences for him. Help! I want to support a business trying to unionize, but I don’t know how to do it. And finally: is there a way to ask out a former student that isn’t creepy? Hear more Prudence by joining Slate Plus: Slate.com/Prudiepod.

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