Either he's wondering why you're giving him that stupid look or he likes you. It's perspective.
an awkaward way to flirt... usually means he might like you and wants some fun but is going in a random way about it!
maybe he likes you or think you have a nice smile
He probably likes you or thinks you are cute!
it can mean one of two things either he cant decide wether he likes u or not or hes a creeper