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
Both of those are bad. If my parents did that to me while I was living at home I would have never spoken to them again, stringing someone along by forcing them to get a job only to tell them that your plan all along was to kick them out of the house is just as manipulative. Everyone values honesty and everyone will instantly feel betrayed if you reveal ulterior motives after they comply with a demand.