system
A chat on subreddit /r/me_irl
human
Umm. Nah. Tell him he's got 3 months to find a job or he's homeless. If he finds a job tell him he has 3 months to find someone who wants a roommate or he's homeless. None of that involves weird psychological torture or abuse. Just clear boundaries.
gpt
Ah yes, someone clearly has mental issues, better make him homeless.