This train of questions "Learning how to cold approach in college -> how to build emotional connection with a stranger -> what to talk about" brought me here.

I never understood why people gave the advice "learn to talk to all people" first and then "talk to women". Until just now. I think when I'm making a conversation with someone I get into analysis paralysis and I often get out of "the moment" due to my worries or analysis. I'm someone who think a lot and who wants to optimize everything. I calculate shortest path when walking or minimize my number of clicks when using my computer.

Is the trick "relax, stay in the moment, focus on understanding the other person and say the first thing that comes to your mind"?

If yes, I have a second question. What if I'm an asshole/inconsiderate/socially inapt? I sometimes say offending things to people without realizing it. And people usually just decide to go away instead of giving me feedback that I hurt them. So I can't spot that I'm doing something bad "in the moment". Or I spot, then I get nervous, then get stuck.

PS. By good conversation, I mean an interaction where other person likes you and actively "wants to" see you again.