Try and find something they like. Let them talk about it for a while and then if you notice something else they say in a conversation ask about that. Start with basic stuff. "What classes are you taking?" "Whose your teacher" "Do you like sports" "How long have you been playing the." Then find stuff you can relate too. normally the conversations will start to flow on afterwards and you can go from the notes you've picked up of the things he's said.
I don't ask anything specific I just carry a casual conversation and let it go from there. You should try it or if you want to ask him questions you can think of some before you see him :)
Ask them about themselves--how they like the class, the food, whatever. Just keep asking them questions about themselves and remember to show how interested you are in their conversation.
Ask them about his life and past relationships. Talking to boys about relationships sends him a signal that you are looking for one.
Just start a casual conversation to start and see if they seem interested too.
What you should ask depends. You can keep your questions open-ended if you don't know them very well yet. Ask them what they did over the weekend. What do they do for fun? You can compliment them on something (their shoes, Gameboy, a recent accomplishment, new haircut, etc.). That should lead to some better questions, "Where did you get them?", "What are your favorite games?" Try to listen to their answer and follow-up with some related questions. If you tap into a topic of interest, you'll notice them answering in more detail. Ultimately, if you like him, you'll want to lead up to questions that will end up with you spending more time with him. If you are at the same school, ask him where he goes for lunch. Ask him if he's seen a movie yet that you would like to see. Ask him if he's going to the baseball/basketball/football game or concert. You can also ask if he's got a blog or Facebook/MySpace account. Then get his online handle so you can chat online.
ask what he likes in a girl! and go for it guys love to get hit on
What's going on? What's new? What bands do you like? Find out what he HATES. CRAZY RIGHT? It works, WHY? You have something to relate to.
"Do you like me?" if he says yes "I like you too." "Do you like me more than a friend." The rest is yours.
Ask them about their life. This shows that you want to get to know them better. You may even want to invite them for a quick cup of hot chocolate or something.
Pretend that you're interested in sports, that works... on me at least :D