This is a sticking point that now that I think about it has been by my side since the very beginning.
Being an introvert, the most game i can practice is at my new school I am currently going to. That means I semi-know everyone I talk to on an everyday basis.
Here is the problem: I am talking to a bunch of new girls that I "have no" problems speaking to, at least when I am not talking about them. Stay with me on this one. Everytime I start a new conversation with a chick it will always either be about: Their weekend, upcoming homework, gossiping(even though i try to stay away from it just because it is sooooo boring) or how life is going in the moment. Sure that is "everyday convos" but that is not what I am seeking to talk about and when I think of better stuff to talk about it allways just seems too weird to talk about. Not that I am ashamed to ask them about their past life, or what they are up to in their spare time But more about it being to late to even talk to them about it just because it's almost expected by now that everybody knows each other in my school. Maybe I'm just overthiking it but I would still like to hear your opinion on this "difect".

Are you in high school?