So I've been asked to unplug a friend - by a common lady friend no less. I don't have many chances - I'm no longer much in contact with him, and we've set up a beer next week - so this one chance is pretty much all I got.

My friend is the pretty classic blue pill. Serial oneitis (I think he's at the third now), and he tends to fixate (obsess?) on his target quite a lot more then normal. AFAIK he did absolutely nothing sexual with any of them, other then being best friends forever and occasionally living together. He may or may not be a virgin. He is around 30, about 50 pounds over ideal weight and none muscle, working in a tech job without much responsibility. Lives with his sister and two cats. Right now he's awkwardly pursuing another onitis (this one slightly less cute and slim) who predictably feels no attraction towards him.

At this point he has invested quite a bit of his self-image into being a blue pill. To swallow the red right now would be to admit he's been a complete fool for the better part of the decade, so I don't expect him to be a willing listener. He probably read about PUA and already has preconceived notions.

The topic we're supposed to discuss over beer is convincing him to accept our common friend buying him an erotic massage for his birthday, something he firmly refused, because "I want it to mean something". (the friend is not attracted to him btw, just frustrated). I could skip it and dive straight into trp stuff, but I doubt he'd be willing to listen. Honestly, I'd be perfectly happy with just one crack in the armor. Does /r/asktrp has any idea of how to achieve this?