My 31-year old friend has never had any luck with girls. He's been feeling pretty miserable about it and has complained a lot about it, to me and my friends.

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Lately he's gotten to know an 18-year old girl. They're getting along as friends, but he wants more. She seems to be exactly his type, but he's a bit too awkward to make a move. She shows some genuine interest in him, but I can't tell if it's just friendly or more.

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However, I'm convinced she is just WAY too young for him. I know they're both technically adults, but looking at her, she might as well be 16 or something. Just a couple of months ago it would literally be illegal for him to go after her. The whole thought of it just creeps me out. Why can't he go for girls his own age, or at least 24-year olds or something?

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So, along with another friend, I've been trying to prevent them from getting together. I already said to her outright it wouldn't be a good idea to ever start dating, but she just laughed a bit shyly. I've tried discouraging him, but he just complains about having been lonely for so long. Me and this other friend are trying to find other ways to keem him away from her.