Well ill try to keep things short.
I have always been introverted and i prefer to remain by my self at almost all times. I have a small circle of friends, thats it and i feel generally happy.
The only outstanding problem is my failure when it comes to going out with women, i have never gone out with one in 20 years of existence, i have shared a handful of kisses, been advanced on, and even got asked out to prom by a hottie (when horribly wrong afterwards) but nothing ever really happened.
So my question is, what can i do to perhaps find a girl i can go out on a date with, maybe in my college classes, without having to entirely reframe my social life, i prefer to be alone, have great laughs with the usual buddies ( think of king of the hill and hank hill with his buddies drinking beer in the alley) and all i want to do is to preferably go out with someone who has similar traits as i do ( introvertedness, similarity in personality, etc).
Now to the second part of my question, aside from gaining skills with women, is the following behavior healthy at all?
I seem to get excited sometimes if i see a girl in college or facebook that i find to possibly hold an introverted personality, for example, i saw two girls in college last semester than interested me because they seemed introverted in class, i found their face books and they were quite the opposite, i have knowingly been exciting my self and have even been jumping at radical conclusions in an attempt to bring some excitement to my life but again, nothing happened as i didnt ask them out, as even if they said yes to a stranger, the idea of going out with someone thats "TOO" social is not appetizing for me atm.
3 days ago i was searching for a girl who was very nice to me in senior year of high school and i was wondering if i could find her and friend her just to be friends but in my search some way or another i found the profile of a girl that i saw in school once or twice and thought she was hot as any other hot girl and never gave it second thought, but instead of just passing by i went to her facebook. By hot i mean hot by my own twisted definitions.
I immediatley decided to excite my self based on the fact that the pictures and posts she makes are of "introverted nature" by what i can analyze, she has very little friends, and some of the ones she has are in relationships with "ugly" people in comparision with me, and her "likes" and everything would have me thinking she is of introverted nature.
I am aware im making some very risky assumptions based on many things, i am aware of this yet i decide to Aaccept it yet again, and now i feel like trying to ask this girl out by saying i saw her and thought she was pretty all while doing so in a "caring way".
My philosophy going into it being of "yolo" in that if she says no i dont lose anything, and if she says yes, might as well give it a try. On top of all of this even her appearance excited me in that she seems "reachable" both of us being 6-7 in a looks scale (whatever that means right?) i am aware that this is all very superficial and maybe even a mental fabrication.
Is this behavior healthy at all even if i am aware of many of its "negative features"?
Even when i think of going out with someone like this girl, she might be just a little bit social than i am and i feel a bit anxious just thinking about it, i think this could all be dealt with, but atm its like im having trouble getting out of my comfort zone.