Start using his name when you say hi. While it might seem like a little thing, it’ll mean a lot for him to know that you know it.
Check out Facebook, if you can, or other social networking. Notice a guy taking lots of pictures of his pet dog? Strike up a convo about dogs. If you’re not sure what a particular guy is into, try finding out from someone else. Talk to his friends. Talk about something you know you have in common, if you know something. If you both are in class together, talk to him about the teacher that you have, or a particular book you’re reading for class, or an assignment.
Start by saying “Hi” regularly, then have a quick exchange or two about something. Talk about that assignment by asking a question. When you get the answer, just say, “Yeah, totally. Good luck next week. Good talking to you!” and leave it at that. It’s good to end on something positive, like, “Good talking to you!” or “Talk to you later!” Often, shy people will have the feeling that they “messed up” every time they speak. So it’s good to leave off with a positive.
Quieter, introverted types of guys are unlikely to be engaged by motormouths. If you tend to fill silences with lots of talking, try to chill out a little bit. Take a deep breath, and create a calming presence to be around. Shy guys will have an easier time speaking to someone like them.
It’s a common misconception that all quiet guys want is to start talking about themselves, anyway. You don’t have to pretend. Talk about yourself, as well. Shy guys, if they’re worth getting to know, will be happy to listen as well.
A great time to have a quick one-on-one conversation is during passing period. You can be “alone” in the hallway, even though there are people around. The bus is another good chance to have a talk. Sit next to the guy you want to talk to. Speak softly. If you’ve identified someone as being shy, he probably doesn’t want a big audience listening in on his conversations. Talk to shy guys in private, using a quiet speaking voice.
Make your questions specific. “How’s your day?” doesn’t give someone much more to say than “Fine. " Instead, ask a particular question based on his interests, or on something you have in common: “Mr. McGurk totally ripped into our group project today. What did he say to you guys?”
It can be a little thing. Talk about pets. Talk about siblings. Talk about where you want to go this summer. Talk about bands you like, or bands you don’t like.
Don’t just wait for your turn to speak in a conversation. Listen closely to what is being said. try to get a sense of his attitude and his feelings about a particular topic based on how he says things. Nod along as he’s talking to encourage him. If you just stare at the ground, or look skeptical, he may think what he’s saying is “dumb” or “wrong,” and want to stop talking.
If you talked about sports last time, try to follow up with something like, “Manning really blew it this weekend, huh? What happened?” It’s also a good idea to try to find something new. Don’t just get stuck on sports.
Don’t acknowledge awkward silence by saying, “Well this is awkward. " What’s someone supposed to say to that?
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?”
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. "
