Soz, for me the hot chick was not always the prettiest and dumbest, it was the one I could relate to best on a physical and mental plane. But what do you do when you feel a mutual attraction, have spent time cultivating a friendship, and want to take it to another level? Well, when you are shy, the answers are not really black and white.
Now, this isn't what you said, but the argument from some women about "just be a man" is also not an option when you are paralyzed to act on your feelings. I don't give a crap whether or not women think this is just guys being pussies. The best anyone can ever do is to try to read a situation, and act on their feelings, period. Be a man, be a woman, the terms are meaningless, useless. It is WHAT YOU WANT, and HOW YOU GET IT that are important, i.e., in a mutual, respectful, equal way. In the relationship arena, both sexes need the courtesy to be strong and weak, depending on the situation, and should support each other accordingly.
With unrequited love, getting back on topic, sometimes things screw up. It happens.
Back in university, I had a female friend who was dead gorgeous, and we had a lot in common. I fell in love, but wanted to cultivate some friendship first. I thought, being shy, that may have been the best approach. We went from your average coffee date, to dinner dates, and later to cooking dinners together at her place with candles, a little wine and soft music. It seemed to me we were making progress. One night after dinner, and many comments on my beautiful brown eyes and curly locks, she said "Let's go to the bedroom and lie down." Okay, I had been bursting to tell her how I felt. We lay down together and she took my hand. We caressed hands for some time (or maybe it just seemed like an eternity). We chatted for a while, and then there was a silence. I chose my pseudo-brave moment, for the first time in my life. I kissed her hand gently, twice. She jumped up and said "What the hell are you doing", and threw me out. She never spoke with me again. As a postscript, I did indeed meet many attractive women after this incident, but none introduced by her.