Dear Prudence,
During COVID lockdown, I had a truly difficult roommate, John. John is a nice person, but lacks social-awareness—he has no boundaries, is pushy and too personal, and generally inconsiderate. It drove me bonkers that I had to explain basic social etiquette AND clean up after him (and that he was the only person I interacted with 95 percent of the time). Since John moved out, we’ve been friendly. I’ve set better boundaries, taking the occasional phone call for updates on his life. He doesn’t really understand that he was a bad roommate.
When my brother Jacob was looking for temporary housing in John’s city, I suggested he could live with John. I stressed that I had a rough time (he knew the details), but maybe things would be different? (Jacob is much better about setting boundaries than me.) Prudie, things have been a mess since the beginning. Jacob is furious and ready to move out ASAP; John doesn’t think he’s done anything wrong and wants me to explain what’s happening. I wouldn’t mind cutting out John entirely after Jacob moves out, but John won’t take a hint. Do I tell John the truth of how I feel?
—Sibling Solidarity