so one of my good guy friends, like the title says, is still a virgin i am going to be 26 in may, he will be 25 in august. we have a pretty close group (back from high school), even though we all went different places for undergrad, masters, law school, etc. he is definitely one of the smarter members of the group, but lacks the social skills that some others have. when we get together and go out, the main thing on most of our minds is obviously girls, and while he talks about them with us, he NEVER pursues them in a social setting. for awhile we just figured he was shy, some people even thought that he was gay (which he is not, that convo has been had), but i now can tell he is just so afraid of being rejected, that he would rather not even try because he doesn't want to face that risk. to make matters worse it doesn't help that some of us in the group have always been able to pull some pretty hot tail, and like all guys we talk/brag about it amongst each other. anyways, a couple weeks ago he opened up to me while drunk saying that he was getting really upset with the fact that he has never even had a girlfriend or had sex, and that he just doesn't know what to do anymore. clearly this supports my judgement that it is all in his head now, and unless it happens, things are just going to get worse. how would you go about addressing this? i have tried numerous times to go up and talk to girls while out, introduce him to her or her friends (hot by the way because his standards are WAYYYYY too high), but every time i do that he either walks away, is a complete dick (and says they were bitches when i ask him wtf) or just acts like a complete tool and removes any chance of a score. i have a couple ideas that i'm tossing around, because i really believe he just needs to hook up with a girl and get the monkey off his back. 1. find a girl from one of my lady friends who wants to "take one for the team" 2. pay a hooker in vegas when we go this summer 3. keep trying what i have been, even a blind squirrel finds a nut sometimes he is not a bad looking guy at all, he makes BANK, his style is not top notch, but he isn't a dirt ball by any means, he just lacks confidence which is what most girls are attracted to. anyone have any ideas?