Hee hee! This all reminds me of the way I acquired my husband! I had a BF at the time, and he knew, and I KNEW he knew, but when it came right down to it, it was "Oh, you have a boyfriend? I didn't know you had a boyfriend", all pitiful-like. What a liar! Always wanting to go for rides, pizza after (and he'd always say "It's a date!", when I'd agree to go, with me insisting it be as friends. I'd always say it wasn't a date.). I spent months insisting we were friends only. Anyway, he was waiting in the wings when I came to the realization that long-distance BF wasn't "the one". 20 years later, he's still my favorite riding buddy.

Having been there, I know how hard it was to just get to the point and SAY I had a boyfriend. It's awkward. However, I do think the probability is pretty high that he likes you likes you. Racer guys on teams don't often hand out their numbers to girls who aren't uber fast (no offense intended - maybe you are uber fast. I don't know what kind of riding you do, but you said something about not being at his level). To me, that's a definite sign. If you're a racer, then not so much.

My DH was thinking "date" on that first ride, where he proceeded to drag me over monster hills, feed me pizza, and then drag me up one more monster hill. He thought I'd like that. I nearly puked on that last hill!

I see nothing wrong with riding with another guy, as long as everyone knows the status of things. Then again, I married the other guy (however, I never belonged with Guy #1). I think it's all about how secure your relationship is, and if you trust yourself.