I have a guy friend that I have kown since I was 3. I felt like I have liked him that long to. I told him once, and almost kissed him, but I chickened out. My mom knows him 2, and is close to him also, and thinks he feels the same way about me. I want to tell him I like him, but he's the most popular guy in school and I am not popular. I don't know what to do, or if he even likes me. He may flirt with me from time 2 time, but I don't know if it means anything.

Maybe in high school popular means something but in the real world it doesn't, so you are going to have to sort of drop the high school beliefs for now and assume that doesn't matter(which by the way it doesn't because nobody remembers the popular people in high school once you leave, because they join the ranks of everyone else).

So now that belief you are going to have to take is he is lucky to have me... not the other way around. Don't be cocky about it, just know that you have much to offer and he'd be foolish to turn you away. Then avoid him for a couple weeks and after he's had some time away from you go up to him and say in a joking manner, "I feel bad for you." He'll say why? And you say, "because you haven't got to talk to me for weeks." He'll laugh, and you say to him, "I'm going to dairy queen(or local ice cream place) after school, why don't you come along, I'll buy you a cone and we can catch up." Now if he doesn't he probably doesn't like you.

Let's assume he says yes, you go on the ice cream date you talk about hannah Montana, Facebook, twitter and whatever else kids talk about. At the end, you tell him he owes you and you will collect. If he says okay, he probably likes you.

Look this is a little detailed and it takes place over time, but at some point you just have to open up and tell him if you want results.