How to Talk to a Shy Boy That You Don't Know Very Well

Have you met someone who you'd like to start talking to? Is he too shy to start the conversations himself? Worried that he's not interested? Have no fear. Read on.

Steps

Admit it; sometimes you just don't want to be seen. Even on your worst days, try to make yourself look appealing. If he acts like he doesn't notice you, he probably doesn't. Go to places he'll be. Put yourself in the center of attention. Make him know that you're alive.
It's probably the most clichéd move in the book, but it actually works! Smiling can make you seem more approachable, and also more happy and fun to be around.
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If he's shy, chances are he won't come to you first. Bring some of your friends, to make the situation more comfortable, and sit near him.
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Talk. Start a conversation with him the same way you would with another friend. Say hello. Introduce yourself, if he doesn't already know who you are. Ask him how his day is going.
- The best conversations usually happen when you take one topic and go deeper with it.
If you just throw yourself at him and drag him into a conversation he doesn't really want to be a part of, he'll get creeped out and most likely leave. Be calm. Stay relaxed, and don't be loud. Anyone who is shy most likely enjoys things being quiet.
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Ask him about his interests. If the conversation is still going well, dig deeper. Ask him what kind of music he listens to. Ask him who his friends are. Letting him know that you're interested in knowing the real him, not just to find out if he's single. It may definitely help him to open up.
- Make sure to not just skip from subject to subject, or the conversation might turn into an interview, making the guy uncomfortable.
- Instead of just talking to him standing there, try doing something different together! Grab a cup of coffee and go for a walk to a neighborhood you've never heard of before or go to a museum and walk around. You will see different things that will turn into subjects of discussion, keeping the conversation engaging.
Make small jokes to show him that you're comfortable around him. This should make him comfortable around you. Talk about annoying teachers or classmates. Point out something funny that's happening on the other side of the room. If he laughs, you've succeeded.
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Know when to end the conversation, and how to end it. If you leaving him hanging by saying, "Well gotta go bye", he'll feel used and probably suspicious. Chances are he won't talk to you again. Instead, slowly build up to an end to the conversation. Say something like, "My friend looks tired. They're supposed to be studying. I'd better go wake them up before the test so they won't fail."
- When leaving, smile and let him know that you want to talk to him again. Giving him your number is a drastic move, especially for a first conversation, but if you feel it went well, go for it!
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Tips

End the conversation in a positive attitude.
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Be careful as to who you bring along to help. If you bring your best friend, she may decide she likes him, too. Try bringing a friend who is happily in a relationship, but who also knows how to be outgoing and friendly.
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Just talk to him as you would another friend. Don't be afraid of rejection or him not responding positively to your conversation.
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Warnings

Don't be pushy! If he seems disinterested in talking to you, immediately, but inconspicuously, end the conversation and leave. You can try again later or just forget him. Chances are he's not worth it.
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Be careful. Sometimes people aren't who they seem to be. Don't go talk to him in the dead of night or in a room without any other people until you know him well.
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Don't get discouraged. This is a try, try again situation. If the conversation doesn't go well the first time, you can try it again, but with, perhaps, a less chipper attitude. Don't get your hopes up too much.
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