This is a little different, but I figured people here might know best. I'm very worried about my roommate (known him since the 8th grade). I guess I should note we've really drifted far apart as friends in the past couple years. He hasn't made a single real friend in 4 years of college and has only had one girlfriend and that was in high school. He takes a big drug cocktail every day for anti-depression, anxiety, and the like, and sleeps until its dark out. When he actually is awake he just sits in front of his computer until he goes back to sleep. He always says he wants to go out more and and meet people, but once he's out the most he does is make other people feel awkward. He's not a bad looking guy, he dresses and speaks well, and is at heart a good person. Yet he just manages to come off as a douchebag or extremely awkward. His idea of impressing or wooing a girl is talking about how expensive something he bought was. He also tends to just be entirely too pushy and will push subjects that are obviously uncomfortable to people. Maybe he doesn't realize? I've taken him out to parties, to bars, to dinners...I've introduced him to the nicest girls AND guys (not sure if he's gay or not), and still nothing. And I don't mean just your typical nice guy and girl. I mean the kind of person that can walk into a crowd of random people and be best friends with everyone within an hour. And yet he still manages to make them uncomfortable. I've even chatted up girls and given him an in and he never takes it. Do I tell him bluntly as a friend what I actually think? Or should I just leave him alone and go out to the occasional dinner or movie with him? I'm sick of trying though and being his only friend here. My girlfriend and I are finally in a great place lately and have been in another honeymoon type phase and every second he wants to know what I'm doing. Cliffs: Long time friend/roommate says he wants to go out more and meet people, but won't do anything with the opportunities I give him.