How to help a friend?

I have this friend who I've known for almost 3 years, he's super nice, always been very bright and one of the funniest people I know. But sort of recently, he's been talking about how alone and depressed he's been been feeling. I took notice a little while back thinking it was just he's been going though at the moment, but its been starting to worry me a little more. He doesn't like being by himself at all which is why he asks people to hang out. But he's bummed that he has to be the one to ask instead of anybody asking him.

He sometimes talks about past relationships, not bringing any of the girls down, but how indifferent he feels when talking to new people and how its been difficult finding some to like and be in a committed relationship with. I'm not a talker at all and would much rather listen to his problems rather than my own, but still do want to help and encourage him to keep trying. He says he doesn't want to come off as a creep when talking to girls,  and I dont know where he got that idea from but knowing him, he doesn't give off that impression at all. I tell him he's overrhing it, but i dont think that what he needs to hear since he probably already knows. I've never been good with words so is there any advice for me to give to him?