OK so this is my first time ever posting.
I'm 26 AFC basically, though I don't know why. Well actually i do know why, I'm shy or have AA. I've had 2, 3 yr. relationships (8's) and a handful of other encounters so I do know how to talk to women, it's just opening or transitioning that is my problem.
I'm a pretty cool guy, I ride motocross a lot and i have my sh*@ together. I Have a bachelors degree, half of a masters degree done, and I work full time making a little over 100k. I live alone in Orange County, CA where there are tons of women. So why am i single I ask.
The last girl i was with was 2 months ago (since my last relationship) but this was an old friend that got in touch on FB. We had a wild 10 days but then I was over it and told her I just wanted to be friends... she told me to have a nice life

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Basically I feel like I should be confident enough in myself to get a 9.5 but for some reason I am terrified to approach or turn a flirty conversation into a pickup. I know that there is nothing to lose, I've read the game, I'm pretty good at being cocky / funny when I get in the groove, I'm successful, I look ok, I dress nice. I'm the most successful person I know out of my friends yet I am terrified to look a woman i don't know in the eyes and put it all on the line. I need to not take it so seriously but that's just my personality... I know i need to relax but when the time comes I tense up.
Just today I was flirting with this receptionist of a business i goto about once a week. I've built rapport, flirted, DHVd, and I think she is pretty comfortable with me. Yet everytime i tell myself today's the day, I choke or find no way to smoothly transition into asking for her #.
WTF is my problem i should be meeting girls. I'm considering going to a mall and saying hello to 30 ppl or going alone to a bar, but geez. i feel like 2 separate people