First, like other people have said, three by 24? There's nothing wrong there, and scorekeeping is dumb anyway.
Confidence is extremely important, but yeah, make sure that's even his scene. I can get by in bars after a fashion, but I've never really picked up anybody that way. Closest I've come is actually getting to know somebody I met at a bar and hanging out separately. I am that guy that ends up in the background in a big crowd.
However, here's something I haven't seen anybody suggest yet: offer him something to be confident about. Bars suck so very badly. In most places that's close to all there is to do, but they cater to exactly one set of social skills, and if that's not your strong suit, you're just never going to get the chance to shine. What's he good at? What can you do instead that might give him a fighting chance to be competitive with you guys who are usually just doing laps while he treads water? In my case, for instance, I vanish into the woodwork in a typical bar, but don't put a karaoke mic in my hand if you ever want it back. Not to overshare, but it turns out that if you can pour your heart into a Killers song, there's a significant fraction of the female population who will just turn into puddles on the spot, and for the guy that can get sick of seeing his friends make it all look too easy at a normal bar, that's a good feeling.
Confidence is extremely important, but yeah, make sure that's even his scene. I can get by in bars after a fashion, but I've never really picked up anybody that way. Closest I've come is actually getting to know somebody I met at a bar and hanging out separately. I am that guy that ends up in the background in a big crowd.
However, here's something I haven't seen anybody suggest yet: offer him something to be confident about. Bars suck so very badly. In most places that's close to all there is to do, but they cater to exactly one set of social skills, and if that's not your strong suit, you're just never going to get the chance to shine. What's he good at? What can you do instead that might give him a fighting chance to be competitive with you guys who are usually just doing laps while he treads water? In my case, for instance, I vanish into the woodwork in a typical bar, but don't put a karaoke mic in my hand if you ever want it back. Not to overshare, but it turns out that if you can pour your heart into a Killers song, there's a significant fraction of the female population who will just turn into puddles on the spot, and for the guy that can get sick of seeing his friends make it all look too easy at a normal bar, that's a good feeling.