Woah there, "Desperate"
Being shy has nothing to do with this situation what you really need to think about is how much you like your job. I mean, I'm all for love and I know that butterflies-in-the-stomach feeling can drive one crazy, but are you sure you can be in love with someone that you only know on a professional level?
You May Be in Awe of Him
Ask yourself if you're not really in awe of your boss...I mean he has power over you and that can be very sexy, but he's your boss. Maybe a small percentage of office romances can work out, but these days its too risky.
He Might Be Married
What if he's married, or already in love with someone else? What if you do hook up and it turns sour? He risks you filing a sexual harassment complaint and you risk your job.
This could have a happy ending, but I just can't see it. I say let it go.
My Friend Is in an Ugly Situation with Her Boss
I really have to say that the reason I am mostly against office relationships is because a friend of mine for SEVEN years, was having an affair with a man from her office who was in an authoritative position...meanwhile he was also sleeping with another girl in the office. The other girl got pregnant, and the two got married, and occasionally my friend, blinded by her feelings for this schmuck, will still entertain his cheating ways... this is an ugly situation for all concerned.
You Will Be a Loser in the Long Run
And maybe this is an extreme case for argument's sake, but don't entertain your schoolgirl crush and don't mistake it for love, because in the long run, you will be the big loser in this situation.