I was going to give you a huge speech on how you shouldn't give a fuck about what other people think and the only people who care about reputation are the socially retarded spastics running around pretentiously calling people "randoms", but then I realized you're a private school kid. So yeah, scratch that. Because networking with other successful people is pretty crucial for your experience in life. You're probably going to want to stay local and use the people you met through private school to create something of yourself, so don't burn any bridges.

You should just take this time to learn from your boss friends. I've personally never seen the 'complete' package out of the private school kids I've met, but if your friends are naturals and pulling then they're far far far ahead of most people. There's no shame in watching your friends and learning. I remember a guy I met my freshman year who had a million dollar mouthpiece when it came to humor and fucking roasting the shit out of people. I'd just watch him do it, pick apart what elements made it funny and tried to learn from him. It didn't ACTIVELY increase my game or whatever, it was probably more weird than it was beneficial, but I still find myself making his style of jokes every once in a while 3 years later and I haven't seen him in a year and a half. I'm pretty sure he's transferring to my college next year so I'll meet up and see. So yeah, small anecdote later, if you got boss as fuck friends, learn from them and mimic their behaviors. Obviously it's not only going to be better, but it's going to be less weird and more congruent for you to make them your own, but that's a healthy thing to do.

I wish I had rich, private school, natural friends to go out with and compare myself to. Holy shit would my game sky-rocket. Nobody aside from me cold approaches at my school dude, they can't even grasp the concept, it's completely foreign to them. So yeah man, you've got yourself a few diamonds in the rough to look up to. Literally the closest thing to cold approach people at my school do is they do the obnoxious social pranks on people.

Why don't you broaden your friend base to public school kids too? I meet a lot of private school kids at the Y or just out and about. Most of them don't impress me with their modeling and horse jumping or whatever gay as fuck parent-sponsored hobby they try to brag about, but I'm sure that'd make you look really cool to 99% of the public school population.

Amuesment parks, the mall, school, other school, sporting events, cafes, etc

And for your issue on not knowing what to say..