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, with Vice writer Noah Kulwin: My mom wants me to discourage my daughter from doing “boy” things. My friends are convinced my boyfriend is a stalker. My girlfriend wants me to come out to my grandparents even if it means they’ll cut me off. My boyfriend has bad table manners, and I’m worried it’s going to have professional consequences for him. I didn’t hit it off with my friend’s brother and now she won’t let it go. How do I support a business trying to unionize? And finally: Is there a way to ask out a former student that isn’t creepy?
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Read Prudie’s Slate columns here. Production by Audrey Dilling.