I've become.. Silly.

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Sometime in October 2009, I joined a school called 'Esteem Academy'. Basically, it's a school for kids with 'issues', such as myself. Though I don't necessarily fit in with the other children, they seem to absolutely adore me.
Anyhow, I've pretty much gotten used to the schedule and such at the school... But, new kids have been arriving lately. And this school is small, maybe 20+ high schoolers and around 12 middle schoolers.
Unfortunately, I don't adapt well to change, and the new students have been setting my anxiety way off the charts. Also, most of the new kids are just plain obnoxious.
Well, about 2 weeks ago the therapist at the school told me of this new boy who had joined, Shannon. Now, she made it extremely obvious that she wanted me to.. Well, date this boy.
I finally got to see him today, not meet him, but see him. And he is absolutely gorgeous. As I was returning to class after a session with the therapist, she whispered to me. She told me how Shannon was 'checking me out' the other day.
I felt myself blush and returned to class...
Now... Shannon is apparently very shy. As am I. I have no idea how I could even work up the guts to talk to him.
But, I've been absolutely bubbly since I heard of his staring at me. And I WANT to get to know him.
I don't know what to do.

Good for you on becoming silly with infatuation, that's a nice state of being One of you will have to break the ice for something to happen with it. That may have to be you, or at least you may have to let him know or someone who talks with him that you are interested in doing so. Since your therapist is involved in this, you may consider writing him a letter for her to give to him, telling him about yourself and saying that you would like to get to know him as well. If you aren't very good at face to face introductions, that is a viable second route. I can totally understand your situation, I've always had the same shyness as well.

I am shy myself, and worked up all the nerves I could to talk to this other shy boy I'd see on my bus and around the lunch room.
Well, after days upon days of awkward conversations and awkward silences, we became good friends. It took a year for one of us to work up the nerve to ask for a date, and it all ended up becoming a year long relationship. We broke up not long ago, and we are still great friends.

Hope all goes well for you!!

good on ya....i think you are really brave

That Esteem Academy sounds pretty cool... Sounds like something I could have used when I was younger.

I'm sure you've already thought of this, but if he's as shy as you, then he probably thinks many of the same things you do. So imagine if he came to talk to you, how would you feel about that? I'll bet he'd feel the same if it were turned around.

If you're simply not sure what to say, you could try out writing out a list of stuff to talk about. Sounds silly I guess, but it could help you feel a bit more empowered for when you do talk to him. If I were in your shoes, all the stuff would be bouncing around my head too randomly or vaguely, but writing it out would help me stay mentally organized. But that's just me.

I'm not sure what sort of stuff happens at this place, but you could ask him to join you on something school related. That way you know you'll have at least that much in common.

Either way, the sooner you take some action, the better.

Good luck!

Get his email address and send him an email. That's how I ask my wife out the first time. It might take some time to work up the courage to hit send but once you do it's out of your hands and you can't chicken out like in a face to face conversation. Might make it easier on him too. You might want to find out if he shares any interests with you first.

My therapist introduced us yesterday. He smiled, waved, said hi, then went back to reading.
Not much, but it made me happy for the rest of the day. (:
I'm hoping, quite possibly, to talk to him a bit more today. ^-^