I’ve tried 4 times, 1 was a complete rejection that nearly ruined a friendship, the second was a weird soft-rejection that led to a friends relationship that felt a lot like I was taking advantage of this person. That ended when they moved away.
The other two led to relationships, one lasted a month and ended with me getting dumped. Second is my current girlfriend.
All of these happened within a year, starting when I was 22. Before that first rejection I had never made a move on anyone because I had 0 self confidence and could only see women as sexual objects. The girl who first rejected me was the first one that I liked for genuine reasons, which allowed me to change the way I looked at women. I now have a lot of female friends and hardly ever think about women I see in a sexual way, when 2 years ago I couldn’t see a woman without thinking that way. I owe a lot to the girl who rejected me, and we are now friends again, for which I am grateful.
She talked to me without me having to strike up the conversation, that was a huge part of it. She was really easy to talk to, and friendly to everyone. She was passionate about the same things as me, and got me out doing things that were beyond my comfort zone. Basically, she was a human being who treated me like an equal human being. There was no disgust at my presence, or laughing at my awkwardness. Those had been the things I was afraid of prior to that.