I'll be honest, the 9 PM curfew on a new college student who is freshly out on his own, trying to stretch his wings and find his own way is EXTREMELY uncool, even if it's the rules of the guest house. Especially considering how long it takes to get to and from school, she is basically making it IMPOSSIBLE to socialize with people of his own age group after a typical day of classes, which is only going to make his social akwardness even worse.
Add onto that the teasing and baiting (even if she is trying to teach him lessons about how to treat women) which is clearly being done because she finds his reactions entertaining... It's pretty messed up. Obviously she sees something that she recognizes in him (either old crush or boyfriend), but that is still no excuse to essentially keep him chained to her guest house.