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Snoop, I have the exact same problem! and i was thinking about how to fix it. Here's how i see it: the reason guys like us run out of things to say is because, well, we'retalking to people weve, just met! we have no prior relationship, and unless youre a social whiz or a big talker eventually things may sizzle out. But this can be prevented! thats why puas use stuff like negs: it creates an emotinal connection, albeit negative, and it gives her a reason to keep talking to you, if only to defend her pride. you can also straight up tell her you think shes cute: its a high risk/high reward approach, cuz if she likes you she has an opening to express it and if she doesnt then shell just blow you off. but at least its not awkward cuz you have a reason for talking to her, and even if she doesnt like you she knows you at least have some balls.
Well, that's the opposite problem to what I have. When I talk with say, my friends or family, they already know everything about me, so we have to create stuff to talk about (which even so often makes for really awesome conversations) but with strangers? It's exploring, and it allows you to talk about stuff you can't talk with people who know everything about you:
Close Friend: I really like steak
You: I went to this amazing steakhouse last night, you wouldn't bel-
Close Friend: Yeah, I know, I was there
I know it sounds ridiculous but that's the best thing (or positive, at least) that can come from talking with strangers - you don't know anything about them nor they know anything about you. Explore, have fun!