Oh, don't be so hard on yourself.
Preety woman are all around, they are for you to ENJOY--not stress over!
You seem to be well on your feet and therefore you know how well you can get along without a girl. Realizing that you don't need one is important, because you can be more relaxed about dating.
However, if finding a girl is important to you at all you need to make an effort. Don't be scared--that's pointless--just set goals for yourself on how to "dick up" (opposite of "pussy up"?) Flirt with that waitress, make yourself do it! Soon your actions will make your conscience realize that this IS important to you, and before you know it you'll have a handful of women you're chasing--with confidence!
I know I sound like a self help book or something
You're such an awesome person, give lucky girls to have that chance to not only know you but be CHASED by you, ... tip: only fall for the ones who chase back! lol, if only that could be helped.
good luck!
<3 Jessica