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Don't make him talk about himself. Don't be afraid to disagree. Don't assume things about him. Don't ask him why he's shy. Don't assume he likes you, or doesn't like you.

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Shy guys aren't just extroverted people waiting to be asked questions. While some shy guys may be perfectly happy to discuss their opinions and attitudes with you, it's more likely that they'll do so if they don't feel like you're wrestling it from them. Get to know him by talking about other things. Let personal things happen on their own time. Wait until he gets comfortable to ask more personal questions. When he starts feeling comfortable, start asking more personal questions as you're following up. "How was the rest of your weekend?" Just because a guy may be shy doesn't mean he's a fragile shell of a person, and it would be condescending to change your opinions or hold things back just because a guy may be on the quiet side. Speak your mind and share your opinions in a friendly way, to treat your new friend with respect and kindness. You can have disagreements but still be friendly by couching things in softer language. Instead of saying something like, "That's stupid," if a guy says Jeter's the best shortstop of all time, say something like, "I can see that. I just can't stand his personality." Many people assume that all quiet people are automatically shy, which isn't necessarily the case. Likewise, shy people aren't either conceited or introverted or anything in particular. If you want to know something about a guy, ask. Don't assume you know. First off, there's no answer to this question. Often, people will ask this question to fill an awkward silence, but it doesn't help and it doesn't give you anything to talk about. Saying something like, "You're so shy!" to a guy who is feeling uncomfortable will only make his discomfort and his silence more strong. Talk about something else. Shyness isn't ever a sign of anything other than shyness. If a guy feels awkward around you, it might be for a variety of reasons, and you shouldn't assume interest either way.