In my friend group there's been this new guy recently, he seems a bit shy and he looks ugly; mouth breather, glasses, acne, recessed chin etc. He's not hideous but he's clearly unattractive and has that stereotypical ugly nerd look.

He's shy in the way that he's very agreeable with what you say, laughs at every joke, repeats kinda unfunny stuff to be "in" on the funny moments, etc. No real contribution in conversations except those forced observations or asking people questions but the interview mode.

Ok enough shitting on him, basically as you can see he's a bit socially clueless and for some reason I wanna help him? I mean it's gay but he sounds nice so far, it's just hard to really talk to him because it feels like there's a layer of social awkwardness and an off-vibe you need to pass through before you get the real him.

My question is, how would you help someone like him? Not like with girls but at first in general, socially etc, to get him to open up and be better socially. I know what you'll say, he hasn't proved himself to be worthy of blablabla idc he reminds me of me in middle school and it's also a nice exercise and I'd feel good about myself lol. So how would you do it?

PS: I've tried some guy banter with him but it didn't work because he didn't really know how to respond so I felt bad and I don't wanna embarass him in front of our group. So I need other stuff. Thanks in advance