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Guy I know, never see him, wanna start a relationship?

So this guy, we'll call Dave, I've known since Pre-K. He actually was my first love, he would tell me I was the "prettiest girl in the pre-school" and would chase me around the playground. we had some wild times, haha.

Dave and I are 17 now, and this past year, since our moms are friends, we got together with his fam and another family. Dave and I sat across from each other and had good conversations, laughs, eye contact, smiling. It was funny how not seeing each other for a whileee could start something like that. he's honestly so cute, and I would love to get to know him more, and perhaps start a relationship. for not seeing each other in 3 years, that time at the table, hit off some good vibes. The thing is we go to different schools :/ And I don't know when the next get together will be with our families, and fam friends. I'll definitely try and stop and say hi if I see him again, maybe at a basketball game or something (our schools are 'rivals' and have huge events for sports). But what if its too late and he picks up a girl by then?

What should I do? Maybe a subtle fb message? A casual 'hey what's up' sounds to personal, I was thinking maybe 'accidentally' messaging him instead of someone else, and seeing if I could casually start a convo then. Is that stupid? ha ha help me! I wanna know if he still thinks I'm the prettiest girl he went to pre-k with haha! To be honest I think we both aged quite well ;)

helpppp!? anyone been in a situation like this too?
Updates:
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Also a little about Dave- He's never had a girlfriend before, isn't one to chase girls (says his mom to my mom haha), is friendly, has a good sense of humor, and we don't really have any mutual friends (if we did I'd be golden :p ).
Guy I know, never see him, wanna start a relationship?
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