Ok I’m probably in the same demographic of women you want to meet (attractive, early 20’s, college educated) and I’ll give you advice on what will get me to go on a date with you, and what won’t. I might seem harsh, but I am being honest.
First off, just because a girl smiles at you DOES NOT mean she is interested in you. I am a very friendly person, I smile at everybody. This does not mean I want to go on a date with them. And if some random guy comes up to me at a library, or some other non-social place, and asks me on a date, that is a turn off. First, I don’t know anything about you, so why would I want to go on a date with you? If you see a girl you like in some sort of non-social setting, it would help to start off with small talk first and then maybe ask for a phone number or something low key like meeting for coffee- but do not ask her off the bat to go on a date.
The fact that you still dwell on things from high school is a huge turn off. Shitty things happen to everybody in high school. Get over it. Move on and don’t let those experiences shape your view of women and dating. If I dated a guy and he still dwelled on things that happened to him in high school, I would run for the hills.
I’m sorry to hear about your mental illness and I know it was something you have no control over, but don’t talk about it with a woman you have just met. From this post you seem very neurotic, and women AVOID neurotic men just like they avoid a power-tool shop. No woman wants to deal with a man who might potentially stalk them or get bent out of shape about something they did or might do (i.e. break up with him). There are plenty of men for women to date so they will definitely avoid the ones who seem crazy. Therapy would help.
If a women rejects you, don’t be so bitter about it, nor keep trying to pursue them because “you know you’ll win them over once they get to know you.” I’m not saying you do this, but it is just a warning. No means no.
An internet relationship DOES NOT mean you are stable enough to handle a real relationship. Honestly, I can’t even believe you somehow logically convinced yourself about this. Interacting with someone IRL is completely different than the Internet. Don’t give yourself props for maintaining this relationship in regards to your love life.
Don’t think just because you get rejected by a girl, she is going to go on to her friends and gossip about you. I have turned down many offers for dates, but I rarely go out and tell my friends about it. It’s just something most normal girls don’t do. Everyone is scared of rejection, and it sucks and you feel like crap, but shake if off and move on. There are plenty of fish in the sea and if one doesn’t like you and you get bitter about it, it makes you seem scary to the women who would want to date you.