How to ask out someone I’ve not spoken to?!

Hi everyone,

I’m a 36yo teacher and I am really interested in another teacher/coach I work with. Normally I wouldn’t want to pursue someone I would work with but I think this is a bit a of a special circumstance: we actually went to high school together (I didn’t know him but we know a lot of the same people) and then wound up teaching at a school nearby almost 20 years later. We don’t work in the same department and it’s honestly challenging finding opportunities to interact. But when we are in crowded rooms, our eyes are constantly meeting and I do think we’re attracted to each other, at the very least. The thing is, when we have had a few opportunities to be in more intimate settings, like a 15 person work dinner a couple weeks ago, we don’t speak to each other and both seem to clam up. This is very typical for me. People see me as extroverted but I do get very shy and anxious around someone I like. From what I can see, he’s also outgoing but is quiet around me as well (though yes, I recognize he just may not be interested in me. But he appears shier around me than others).

I’ve felt this way for a couple months now and don’t know how to move forward. Obviously if he’s truly uninterested, I’ll have to understand and move on but i think I’d be doing myself a disservice by ignoring this. My work friends who have interacted with him say he’s incredible and kind and would be great for me. I just don’t know how to even open a dialogue to see what’s there. I’d love the male perspective and any advice from women who’ve been in the same position!

Thank you!!