How to Start Conversations With Shy Guys

Ease that shy guy into a great conversation.

So you can't figure out how to get the quiet guy in your class to notice you. Perhaps the last time you tried to have a conversation with him, it was awkward because he barely spoke. Shy guys may be nice and sweet, but it is not easy to talk to them. If you are really into a guy you know is shy, you have to take the initiative to start a conversation with him. Approaching him in the right way and asking him the right questions will help pull your shy guy out of his shell.

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Instructions

- 1
  
  Approach him in a gentle manner. Shy guys are not likely to go for the loud, bold woman that gets in his face. Even if he likes you, he may be turned off by that type of approach. Take things down a notch and go for something much more subtle by simply catching his attention, smiling and saying "Hey." Don't try to get his attention from across the room; instead, walk up to him. "Accidentally" bump into him if you need to to get his attention. Just be casual and don't make a big deal out of trying to talk to him.
- 2
  
  Compliment him. Guys, no matter how shy they are, appreciate being complimented. Don't make a remark about his body or eyes though, because that might embarrass a shy guy. Instead compliment his outfit or an accessory he's wearing. For instance, you could say something such as, "Nice watch! Is that a Movado?" or "Most guys have a problem wearing pink, but you pull it off well." Or if you've just seen him play a sport, you could compliment him on his game.
- 3
  
  Ask him questions with detailed answers. Shy guys tend to give one-word answers. You have to get him to talk by asking him questions that he has to answer with more than a yes or no. Ask him questions such as what his favorite sports are and elaborate with follow-up questions such as who are that team's best players and who's going to make it to the playoffs this season. If sports aren't his thing, keep trying with other subjects until you hit something that sparks his interest. Once you discover that, he will be more comfortable talking to you about something he's really interested in.
- 4
  
  Subtly ask him out. If the conversation is going well and he seems to be responding positively to you, ask him out in a non-direct way. A direct approach -- telling a guy you want to go out with him -- works for many guys, but a shy guy may not know how to handle that, so keep it casual. Let him know that you want to hang out with him again by saying something like, "We should definitely hang out sometime." You also could use something the two of you have in common to try to spend more time with him. For example, if the two of you like to bowl, you could say, "We should go bowling next weekend and see who's better." If he's into you, he will definitely say yes. If he comes up with excuses and avoids eye contact, your shy guy may not be into you.