I'm uncomfortable with the amount of women my roommate has over. Do you think I should tell him?
What women does he bring over?
Sometimes boring hookers and sometimes girls that I like
I would feel uncomfortable with that as well. I would talk to him about it and hope that he understands.
You're overanalyzing. I just want to make sure he doesn't have them all over all my shit.
I would be concerned with that also. I think you would feel better if you have a conversation about how much company he has. Then he'll know that you're concerned about your stuff.