Should I flirt anyway?

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Do you have some advice for this person?

Visitor's Question:
Okay, so there's this guy at school in the hour that I have band that I've become really head-over-heels over, but while some girls become more flirty the more they like a guy, I'm the kind who totally clams up around the guy I like. This has happened before last year w/another guy, but this time it's a lot harder. I've become so much of a clam around him that now most - if not all - of the band thinks I'm this shy, smart, goodie-goodie two-shoes girl. And the thing is I'm not - well, except the goodie-goodie bit. Away from school and in more casual, out-and-about settings, I'm really extroverted, will talk to anyone, and not afraid to do outrageous, goofy things.
The problem is that each time I try to be myself with the guy, some mental obstacle keeps me from doing it. Sometimes when I plan ahead like the class period ahead or something what I want 2 say to him or how I want 2 joke around with him, I clam up or I get so nervous that my comment or the thing I do doesn't work as well as I thought it would. Other times I would come close to doing it, to flirting with him, but then I'd lose hope and think to myself it won't work. It would be awkward if all of a sudden this supposed plain-Jane girl made a funny just out-of-the-blue, you know?
Basically my problem is I want a second chance with this guy, but I'm not so sure how to do it. The last time I asked for advice, it said that I should take the flirting at a gradual pace, but when I tried doing that I kinda got to one point, and then I got nervous or something and I'd give up. So how should I do it? Is it too late in the game to be myself and see if he'll take me for as I am? Will he be able to look past the facade I've had since the beginning of the school year, and see my "inner light"? Will the transition be awkward? And how can I just flirt with him without getting nervous or planning ahead what I'm going to say and how I'm going to act? Or should I just be myself and not worry about how the guy or the rest of the band group will react? See, when I try to plan ahead what I'll say around the guy and how I'm going to joke around, it just makes me seem even more awkward and shy, and when I try to take the flirting step by step, I get to one and I can't seem to move on to the next.
Yeah, I know this is a tough problem, but I will so grateful if you help me with this! Thanks for reading, and i will take your advice this time! :)

Our Suggestion:
Why not take some of the burden off of yourself.

Do this by pretending to yourself that you are not very interested in this guy. Imagine that you are just practicing on him for some other guy in the future. And, guess what, that is exactly what you will be doing. Someday this guy is going to be gone (he is older than you as you know) and you will be interested in someone new. You don't want to go through this shyness over and over. So, instead of clamming up, just think of him as a regular guy that you are practicing on.

This won't be easy at first, but the more you do it the easier it will become.

Good luck! George

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