Joe,
I take it that you have no sisters. Am I right in this assumption? I always tell young'uns (I have always been very shy, myself) to always treat a woman like a sister (or mother). When you find the right one you'll start treating her like a prospective lover instead.
One of the greatest pains in life is the "what if". The greatest regrets are those where you chide yourself for not doing something. I have always regretted not asking a certain woman not to marry me. I know that she would have said "yes". But my vanity, the thought of "something better" being "out there" caused me to act ir-responsibly.
When you see someone you like, just go up to her and say hello. Make believe you are speaking to your sister. After 30 seconds you'll know if you like each other. See through each other's games. (We all play them. We like to rationalise them as "defense mechanisms" and "personality". The truth is that we are all afraid of making commitments). (I have known a few guys who always ended up with psycho girl friends. Their forethought was always centred around the sex.)
The fact that you like her says that she must be a lot like you. So chances are that she will like you, too.
On a personal note, I would have composed the letter thus:
"It has been said that life is too short. That life is full of regrets. But as I am not experienced in the ways of the world, I can therefore only seek out what is beautiful and good in life. Like a moth to a flame, your beauty beckons me forth. I yearn to see your smile, to gaze into your eyes, and to hear your sweet voice. I have admired you from afar and now find that the image of your beauty can not be erased from my mind by the oblivion of sleep. I would like to break bread with you, perhaps with a small bottle of wine. Could we share a cup of coffee and a walk in the park? It would be our second meeting.
Then send her one rose, closed, with the thorns removed. The above would be on a card, with your name and phone number. I just hope that she remembers you.
smile alot. be yourself. hey, WE like you. chances are she will too.