Hello. Girl here. It's tricky. Sometimes you have to intuit it. If you feel even the slightest bit annoying or creepy don’t do it. Girls are not stupid. We do not forget when a guy has expressed his interest. If we reject initially that means please leave me alone for now, but i will not forget that you are interested. And if she feels like it she will re connect with you in the future. Or she won’t. Don’t wait around for her. I would suggest putting more of your focus into becoming fully emotionally independent as a man because subconsciously women pick up on this and love it!
Good luck and always remain mature and dignified regardless of how women behave towards you x