Let go or try again?

I met a young woman nearly a decade ago when we first started college.* Due to a life full of social anxiety disorder, I failed to have the confidence to approach her and upon the day in which I did, she dropped the course.
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Eventually, I found her on MySpace.* I admitted having had feelings for her and told her that I wished to give her a gift which happened to be a wooden wristwatch I had crafted.* In fear of never knowing her, I told her that I only wanted to be friends. I probably terrified her and she rejected me saying that she was "having problems with the male race" and deleted her account.
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Pathetically, I didn't stop there and messaged her friends.* Most of them were non-responsive except for one who said that she was a private woman who wasn't trustful of men because of the relationships her friends had been through.* Her friend also said she would be amazed if this woman ever got into a relationship.
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As a relatively private introvert, I did not take it well and made some drastic changes the following years. I moved to the Pacific Northwest and ended up finishing school in another state hoping to greet social change. It was indifferent. After school, I did it again and went to Japan. I worked for a Global 500 chemical company for 3 years before finding my niche in derivatives, international stocks, and forex. After more than 5 years in Japan and Korea, I returned to the states 8 months ago and my social life still does not exist.
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I have tried datingto a small extent. Coworkers and long time acquaintances have introduced me to friends and family and they have never worked. More recently when I had a joint seminar in New York, subsidiary hedge fund sent me a high detail escort.* Every time and every woman, I only thought of her.
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I do not know why I admire her so much. Perhaps my memories of her were that she is just so smart and conscientious and carried herself in such a respectable yet reserved manner that I cannot let go. Or perhaps, what the psychiatrist says is true and my inability to let go and fail has become a detriment to my mind.
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I have a wedding to attend this winter in the Orange County, California where I grew up and where I met her. I'll be lending my GT2 to my older brother. He tells me if I really cannot give up, i should try one last time since nearly 9 years has passed since i may have disturbed her.

I am afraid of instilling the fear I may have once brought upon her and if she realizes availability of resources and expenses I have, I do not see a reason why she could not conclude that I attempted to manipulate a situation.

So, I am curious if you fine chaps happen to have any ideas of how I can approach her without seeming like an infatuated stalker. Any other opinions, insights, or psychological evaluations would also be fine.

By the way, my brother devised an idea whereas I purposely crash into her vehicle. Coincidentally, I would remember her and confess something. I do no like the idea because it essentially employs my financial life to an extent. On top of that, I suffered from severe social anxiety disorder until I left this country in 2004. I think it may emerge if I see her.
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I expect some insults and jokes. I am a pretty self-deprecating person so good insults can bring an enjoyable grin. Thanks in advance for your insight.

DcL

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So, I am curious if you fine chaps happen to have any ideas of how I can approach her without seeming like an infatuated stalker. Any other opinions, insights, or psychological evaluations would also be fine.

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How do you still know how to even reach her since you haven't seen or spoke to her for 9 years?

Anyway, I think you should talk to your therapist and ask him/her how and what he/she thinks you should handle this. You sound obsessed and it also sounds like you use our social anxiety as an excuse to stay stagnated.

So: How do you still know how to contact her? .. and .. If you still do know how to contact her, why wouldn't you just go ahead and say hi. Running into her with your car is ridiculous IMO and your brother, if serious, does you no favors by enabling you to be so socially inept that you'd cause harm.

9 Years is a long time to be carrying such a torch either talk to your therapist about strategies to help you forget her or, talk to her and find your answer.

I was going to say that I am socially fine but I am thinking and have been thinking of a woman I barely knew for 10 years. Still, she hasn't caused much stagnation. It's only in an area of personal life that has existed since the dawn of time.

Anyways, seeing the psychiatrist is pointless. She is there for the betterment of the fund. Introverts being introverted and preferrentially nonsocial is apparently fine as long as it doesn't complicate one's well being and other aspects of life. I don't have problems which complicate my trading performance. Her advice have only been as typical as question responses to questions atypical of overpaid epiphany-inspiring psychiatrists.

Your insight is useful, though, and leans towards what I have always tried to do but could not. Your response is very much appreciated.

I honestly think you should try again and if she rejects you then its time to move on. you have spent far too long thinking about her and probably missed out on other matches. Its time to look elsewhere, life is not about infatuation it needs to be mutual.