Chat with him. If he is online simply say "hey" but make sure you don't always start the conversation though let him sometimes.
If he replies, say "cool" or if it is a negative statement say "that's crappy, are you ok?", unless he says "what about you?". Then simply say you are fine or nothing much is really going on.
Relax. It's over the internet... not even face to face, it's very simple and don't freak out.
Laugh at his jokes. Laugh at his jokes even when they aren't funny. Guys like that.
Ask him about something he likes. Maybe he's a music lover, ask him his fave song. Or sports type, ask him his fave team. You get the idea.
If he isn't online, send him a message asking about a current event going on in your area. Nothing going on? Ask about homework if he goes to your school. If he goes to a different school then say your friend had mentioned that he is funny and you two could be great friends.
If he talks to you for hours, that is a good sign. Make sure he is single though.
Talk to his friends. Make sure he likes you before you ever mention a word of you liking him.
If you ask him out.... never do it online. Always make it in person. Unless you can't.
Say something funny. But don't try too hard and don't laugh at everything he says. Especially if he's being serious.
Be confident! If you don't trust yourself, how can he?
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