Ask out or not?

Nicole • I'm a nonbinary girlflux lesbian, and 16 :)

So there's this guy I've known since preschool. His house is a few down from mine, and we both go to the same school. We are both in 8th grade and have 3 classes together. We used to hang out alot when we were younger, and lots last year, but not as much this school year. He's been single for over a year and the only relationships he's been in were because of dares or popular girls just dating him for even more popularity. He seems to be flirting with me when we talk in homeroom. He sits right by me and my friend. I'll occasionally buy him candy or popcorn (when our school sells it in the cafeteria/office) and he always jokes with me and has the same sense of humor as me, he's just not as dirty as my though. But since I'm a tomboy and I've always been able to talk to guys easier than girls. We laugh and chat alot, but I don't know if I should ask him out or not. I've liked him since 3rd grade. I don't know if he likes me or not. I'm not pretty, have tiny microscopic boobs, and I feel like I'm acting desperate. What do you all think I should do? Thank you all so much!

(Btw, yes I'm copying and pasting this from my original post, and I'll be posting this a lot because I need lots of advice. Ok bye)