I'm shy so how do i talk to this quiet guy at my lunch?

[~:Peace:~]

so there's this guy at my lunch and he's quiet, doesn't talk to anyone, he's kind of a laid-back guy. he's like 15 and im just about 15. anyway i think he's really hot and i want to talk to him but im super shy i don't want him to think im weird and scare him off. so how do i approach him and how should i start out the conversation besides hi and keep the conversation going without boring him? the guys have always asked me out but ive only gone out with one guy who asked me, and ive been called pretty, hot, sexy, gorgeous, etc... but i don't have any self-confidence so i don't believe im all that. how can i gain self-confidence around this guy? and how can i get him to ask me out or would it be weird if i asked him? if not, when should be a right time? thank you. sorry about the azillion questions haha i just don't want to mess this up.