How to Talk to a Shy Guy

Making Contact

Start saying "hello" on a regular basis. If you rush up to a quiet-type and start peppering him with a million questions, you're more likely to get a blank stare and a bunch of one-word answers than a good conversation. Ease into it. When you see a shy guy, start saying "Hello" as you pass in the hallway. Smile, give a little wave, and know that you're making progress. 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.

Use open body language. Open body language means you've got your head up, your shoulders back, and your limbs uncrossed, suggesting that you're willing to talk and open to listen. Shyer types will be much more likely to open up a little bit and mirror your body language and behavior, so it's a good idea to try to adopt open body language to help out the process.

Try to figure out what his interests are. Shy guys will have an easier time talking about things outside of themselves. Music, sports, movies, books, even the weather, are all better topics for a shy guy than to try to prod him into talking about himself. So, asking, "What'd you think of Walking Dead?" will be a way better question than, "How was your weekend?" 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.

Keep your interactions brief. Often, shy guys get nervous when conversations last more than a little while, because they're scared of messing up, saying something dumb, or drawing a blank when it's their turn to say something. Don't force the issue, especially at first, by keeping your conversations short. 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. EXPERT TIP Eddy Baller Eddy Baller Dating Coach Eddy Baller is a Dating Coach and the Owner of a dating consulting and coaching service, Conquer and Win, based in Vancouver, Canada. Coaching since 2011, Eddy specializes in confidence building, advanced social skills, and relationships. Conquer and Win helps men worldwide have the love lives they deserve. His work has been featured in The Art of Manliness, LifeHack, and POF among others. Eddy Baller Eddy Baller Dating Coach Give him physical space while you're talking. If you're having a conversation with someone who's really shy, take a step back to give them more space. That can help them feel more comfortable around you, and it will make you seem more empathetic, since you're not just barging into their space.

Go slowly. Lots of quieter types are perfectly communicative and articulate, but struggle to interject in louder or faster types of conversation styles. Just as speaking very quickly isn't a sign that someone is saying anything interesting, speaking very slowly isn't a sign of simplicity. Wait out his pauses and go more slowly than you might be used to. 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.

Getting to Know Him

Be yourself. Whether you're shy or super-extroverted, funny or somber, sporty or dorky, the only way to get to know someone better is to be yourself. Even if you don't have the same interests as this shy guy, you shouldn't pretend that you do, just to get to know him better. 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.

Talk to him one-on-one. It's much easier to talk to a quiet or shy person one-on-one, compared to a larger group. Don't try to talk to this guy when you're with three of your friends, or at a big lunch table, or in class. Wait until you've got a minute in private to talk to one another, and you'll probably find him much more willing to talk at length. 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.

Ask open-ended questions. If a guy is shy and you ask a closed question–a question with a yes or no answer–you're going to get a one-word answer almost every time. Learn to ask specific and engaging questions if you want to draw someone out and give them something to talk about. 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?"

Look for something you have in common. As you're gradually talking to this guy, try to find something that you have in common and can talk about. Even if it's not big, having some common ground or common attitudes to share will help make conversation much easier. 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.

Be a good listener. It's important to practice good listening habits any time you're having a conversation, shy guy or no. Make eye contact while you're talking, showing that you're listening to what he says. Summarize what he's said after he says it, or respond to it in some way, to show that you're listening. 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.

Follow up on old conversations. Often, the second conversation is more difficult than the first. Lots of times, shy guys are afraid of starting conversations, because they're afraid you'll have forgotten what you talked about next time, or don't remember talking, or that you don't want to talk. Make an effort to remember what was said previously and follow up on the conversation. 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.

Share silence together. Awkward silences don't need to be awkward every time. Sometimes, shy guys won't have a whole lot to say, and you don't have to stretch to fill the silence with a bunch of talking. If it gets quiet, it gets quiet. Just sit together for a while and think of things to say. No big deal. Don't acknowledge awkward silence by saying, "Well this is awkward." What's someone supposed to say to that?

Talk online. Introverted types often have a much easier time communicating in writing, because it gives them the opportunity to revise. While it might seem less personal, striking up a conversation with this guy online can be a good way to get to know a little about him, to give yourself a chance to talk more in person later.

Avoiding Shy-Guy Errors

Don't make him talk about himself. 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?"

Don't be afraid to disagree. 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."

Don't assume things about him. 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.

Don't ask him why he's shy. 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.

Don't assume he likes you, or doesn't like you. 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.