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How to talk to shy boys?

This boy looks at me all the time and has for a couple months, but we've never talked. I figure he's shy and scared to initiate conversation, even thought he acts pretty outspoken and outgoing with others. He'll talk to other people around me when were talking to friends at the end of English class, but he'll avoid looking at me or talking to me, which I don't understand?

What can I say to strike up a conversation? I was thinking about asking if he went to school last year and where he came from and stuff, but how will he react if I try talking to him. I'm very shy myself, so advice on how to look flirty/ nice/ available to talk to... would be very appreciated. Thanks.
How to talk to shy boys?
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