Message him on Facebook or get his number and text him. I'm shy and when I'm talking to people I don't know that well and still feel shy around (especially someone I like) then I feel more comfortable doing it through fb or text first until I get to know them better. It just makes me less nervous, and then there's no awkward pauses and I don't have to try to think of what to say to the person I barely know. If you don't have his number and one or both of you guys don't have a fb, then tell him that you need help with something for the class and then ask for his number. Text/message him and ask a question about class, then when he answers say thanks and then say something about the class. You could talk about how hard it is, how boring your teacher is, how scary your teacher is, bring up a funny time in class, or anything that could start a conversation. With this, you could bring up other stories. Like if you guys are talking about how weird your teacher is then you could tell him about another weird teacher you have/had and share a funny story, and then maybe he'll have one to share too. I think that's the best way to start a conversation casually. Then you just have to try to keep it going. Ask him questions about himself so you get to know him, and respond with something about yourself too so he knows you better too and will know what to talk about with you. Try to find a common interest and talk about it. At school, try to be friendly and warm towards him. If you act too out there or bubbly/loud, it could make him feel uncomfortable. Smile at him, laugh when he says something funny, let him know that you enjoy talking to him. There are different reasons why a person can be shy. I think I covered: feeling uncomfortable, not knowing what to talk about, and insecurities so far. Keep those in mind when you talk to him so you don't make him feel less shy. Maybe compliment him on his shirt or something too so he feels more confidant about himself. He's also more likely to compliment you if you compliment him first. And if he doesn't talk to you in person right away, don't worry, just wait. Depending on how shy he is or how comfortable you make him feel, he might have to get to know you better through messaging/text first until he talks to you in person more. If you see him around school, say hi to him and smile so he can gradually get more used to being around you and to talking to you. Also try joining his conversation with his friend. I feel more comfortable when I'm around my friends, so if I meet someone while I'm with my friends, I'm more likely to be open to that person and less shy. That might work with him too, so join their conversation so he'll continue talking and feel less nervous.