How should I talk to him whenever we see each other?

Well, there's this guy I've been liking for a while now... it's almost been a year but we haven't gotten to know each other well until about a month ago. I met him when he was a senior and I was a freshman, but now he's in college and I'm a sophomore in HS, but he and I have a lot in common. We don't get to hang out with each other but we have a lot of conversations on Facebook.

My question is a little one. Whenever we're both on Facebook, do I initialize the conversation or does he? Whenever he says hi first we talk longer, probably because he has more time to talk. Whenever I say hi our chats are short and he usually has to leave. I want to talk to him but if I say hi to him every time he's online maybe he'll find me annoying or something. I'm kind of shy but I open up quickly whenever I talk while he's a little bit more shy but also talks to me about a lot of stuff. Sometimes I just wait for him to say something but he doesn't so I regret not taking the first move to approach him. I'm a bit stuck in a rut. Advice?

Also, if there's anything I should say or do to show him that I'm interested in him would be nice too. Thanks. :)
 
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