@imastarwarswhatever; Uhm, no. That’d scare him off.
Are we talking, cute popular boy, crunchy on the outside but you Hope soft in the middle? Cuz they’re usually crunchier than you think, and it’s best to go for someone a bit creamier.
Peanut butter… Mmm….
Anyway, I say be confident with your image and personality. You’re probably prettier than you think. Talk to him like it’s no big deal, and pretend that you don’t know you’re flirting.
If he doesn’t respond after a couple earnest tries, he’s probably not interested. Try to go after someone else, maybe a bit less obsessed with the popular girl.