Guys, did you ever like an older girl?

So im in marching band and i am a junior. there's this freshman guy in my section who will not stop staring at me. I've noticed it for a couple months now which is really only as long as I've known him. I tried to be friendly and nice at the beginning but he was super shy. Now he talks more but when i talk to him or crack a joke he gets this goofy grin and just goes red. The other night i sat by him in the bleachers at a football game and we talked all night. I think he feels nore comfortable around me but he still blushes a lot and now he tends to always be around me and its almost annoying. I dont want to lead him on but then i almost kind of like him and thats just weird to me cuz I've never liked a younger boy. Guys, did you ever like an older girl in high school? Did you feel like it was hopeless and is it weird? I don't know what to think. Does he like me?
Guys, did you ever like an older girl?
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