First time poster here, just recently started looking at this subreddit. Lately I’ve been trying to reevaluate how I engage people on a social level as well as creating interest in me within women. I realize a big part of talking is to just talk without thinking and that you can talk about almost anything to stimulate conversation.

My problem is that I never know how to transition.

I feel I’m not the best at telling whether or not someone is into me, and yet it seems like so many people around me can just hop in to a hookup or date with anyone they choose. If I’m interested in someone/talking to them how do I transition the conversation to a more intimate topic without coming off as creepy or too pressuring?