I've been told that I am a really confident guy by many people - I was hitting on a chick that this older (later 30's?) black guy was hitting on as well, he was doing pretty well for himself and in the end I worked my magic and won. His only words upon leaving were, "Man, if I had the confidence you do, I would be running this joint"; it's been one the greatest compliments someone has given me in the recent years. I rarely have issues regarding social situations and I've done well for myself on the women front; words that are generally heard about my presence are manly, awesome and hip as fuck. Now, I've got a friend, who doesn't quite meet those qualifications; mainly because he's not confident in himself. He's one of the smartest people I have ever met (in a long line of smart people I've met); academically, he's beyond anything I'll ever reach; he has a decent job, a good education and holds his own in a comfortable social situation (by comfortable, I mean with established friends). He's also been on an amazingly long dry spell and is getting somewhat depressed at his inability to meet and enter romantic situations with the ladies*. In the end, it's the simple fact that he's not confident enough to go out and try; so, as the good friend I try to be, I've been brainstorming ways of helping him build his confidence. He's not incredible looking nor is he ripped like a mother fucker; I've told him many times that it's not how we look but how we project ourselves. Hell, I'll even admit, I'm kind of goofy looking but that hasn't stopped me. I realize the only way someone gains confidence is to put themselves into situations that they're unsure of how to handle - failure, uncomfortable, awkward and plain terrifying moments are what builds a persons character and ultimately their confidence. One idea was to have him find an interesting fact (on wikipedia or something) and when we're at the bar, he has to present this fact to no less than three women while maintaining some sort of sobriety**. He'll either hit or miss, both options are good as it's a learning exercise right now and after he has talked to these women then he can rejoin us in shriveling our livers. I've tried wing manning for him but he doesn't have the confidence to take off from there, I can't babysit him through these things if he's unable to help himself. FOCUS: Tips and tricks for gaining confidence. I'm not interested in directing him towards that stupid fucking PUA or whatever the fuck it's called. I'm talking ways of building his confidence permanently. Do you have a friend who was like this and you brought him up to speed? How did you do it? *He's been on one date, last week, but doesn't think he's good enough for the chick he went out with and isn't going to call her back - it's idiotic because it sounds like she's into him **It's quite possible my plan will backfire and he'll end up dead from alcohol poisoning.