Boy trouble

I’ve known this guy since the 4th grade. He’s liked me for a long time and I’ve always turned him down. Me and my friends used to tease him behind his back and I kinda feel bad about it now. We spend a lot of time after school together because of the school play and I’ve been talking to him a lot more recently. He’s seems really sweet and he has a lot of qualities that I look for in a guy. But, he also has qualities that are kinda major buzzkills. I definitely don’t think my friends would approve of us dating nor do I think he is allowed to have a girlfriend. I’m realllllyy stuck. Should we just remain friends?