How can be nicer to a person who's socially awkward by not sounding like a jerk?

I first might this dude through another friend at community college. I mean he seems like a nice person but he's very socially awkward. Doesn't have a lot of friends and believes everyone should like him. He tries to invite himself to other's social gatherings without consent. In addition, he's kind of a stalker, because he keeps asking questions about my lady friends. He keeps whimming about why he doesn't have a relationship with a girl & tries to ask me for help. I want to hang out with the person but he just doesn't know how to socialize other people properly. Always asking personal questions, wanting people to drive him everywhere, etc. By the way this person is only 25 years old.