Some personal stuff below.

I have a friend who is the kind of person who is "friend zoned", in that he never expresses his attraction for a lady until they're 6 months into a friendship, and when she inevitably rejects him, is very heartbroken. This is a guy who has never had a serious relationship, and no dates in the last like 4 years of his life. He's the type of guy who, under the right cicrumstances and let his pain consume him, would potentially evolve from nice guy to a Nice Guy TM.

He's got major desperation and insecurity issues, and he posts a lot of depressed lovelorn stuff on Tumblr. I want to help him, but it's continually frustrating to watch his progress, because it's one step forward, jump back to the beginning and crumple up into a ball of heartbrokenness. I really just want to figuratively slap the hell out of him and yell, "dude unless you work on your shit, teh ladayz will continue to avoid you!"

The thing that is particularly frustrating is that he will fall in love with a girl without building any sort of relationship with her, and I really want to tell him that he doesn't actually love her, but the idea of her. He doesn't fully know who she is, but he knows what he's projected onto her, and he's infatuated with that.

I just... I don't know what to do with this guy or how to react. He approaches relationships like he's still in high school, despite being well out of it. Should I just give it up and try to let him be? I want him to be happy and not lonely, but it's so frustrating to see him sabotage himself.