Gaining Skills with Women, and is the following "healthy" behavior?

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.

Whatname, between what you describe in previous posts and what you are describing here, i would say that your issues are far more significant than garden-variety introvertedness. In a previous post, you mention being so worried about having to hang out with a girl's friends - now I can guarantee that this girl will have friends and you will need to be social as part of your role of being boyfriend.

For now, forget the girl. It's far more important to address your issues and overcome them. If you don't, they are likely to drive even an introverted girl away.

Are you sure you are not agoraphobic? I would say you need a girl who can bring you out of your shell, introduce you to new people, make new friends, have a more active social life and have some fun.

Why would you want a girl who is just as shy and lonely as you? So the two of you can sit in the dark together 24/7 coz your both two afraid to leave the house and you cant afford the electricity bill coz neither of you work out of fear of having to talk to someone you don't know?

I agree with b&t. I think your OCD is unhealthy and your fear of making friends is even worse. Your in college now, you are grown up-nothing to be afraid of. Its not like being bullied for wearing glasses when you were 13. Most college kids are more mature. I think you need to face your fears and conquer them.

Well when i was smaller, i was introverted as well but i didnt have the fear factor that i now kinda have, of meeting people.

I guess id want a girl that is as "shy and lonely" as me so that any social development can be done in more of an equal pace or ground, you are right in that i need a girl who can bring me out of my shell.

Sometimes i think of situations like, meeting new people, going on a date, depending on my mood at the given time, my visualization of what can happen changes, sometimes i feel confident that i could move forward and do a good job , be funny, be "my self", and other times i imagine my self being uncomfortable, nervous, etc, maybe i can try to have a different attitude towards all of this. I am aware that i make too much of a drama of these things, i overthink too much.

social anxiety. have you ever considered counselling?

I have but too "embarrassed" to go further.

Along with some disinterest rooting from me thinking i maybe dont need it..

whatname, isn't seeking help and overcoming a problem less embarrassing than staying hidden inside?