Sorta similar to my situation. I have actually, never asked a girl out in my life. And i've been asked out about 5 times.
Life is a drag man, you never get what you want. Its either you like a girl for who she is, but shes not that great looking, and you dont wanna go out with her because you would get made fun of, and i know everyone says "Its the personality that counts", but yea, easier said than done. But, your a good looking guy, and with that you can expect random girls to ask you out
Just keep your cool, try and make friends with a girl you've had your eye on, and see what happens. Its worked for me once