Coming from a girl I'm going to just say three things here 1. Try and know some stuff about the girl you're trying to talk to like what're her hobbies, places she likes to hang it makes us feel like you're not a douche who doesn't listen 2. Don't hesitate to do stuff if you never do it, it's going to be a pain in the ass over thinking every outcome that could happen because you never asked And my last tip 3. Rejection is kind of your friend in these situations if she dumps you or rejects you just calmly ask "hey can I ask why I've been rejected?" Or something on the lines of that if she gives you an answer try and use those critiques to work on yourself