Make the first move. Women traditionally wait for men to seize the initiative, but that won't work with a shy guy. It's up to you to step forward. Be casual and keep the conversation light. Don't be in a hurry to get anywhere; it may take time. Give him a chance to respond when you talk, but be prepared to hold up the conversation on your own if you have to. As he opens up, the exchanges between you will grow more balanced.
Use body language to help him relax. Look him in the eye when you talk and smile quietly at him. You want to let him know that you're not a threat and that you won't laugh at him or make fun of him. As with other aspects of attracting a shy man, it may take a little patience before your efforts pay off.
Look for conversation topics of mutual interest and use them to get him to open up. Find out what his passions are, the things he really loves to do and the hobbies that occupy his time. If he lights up when a particular subject is mentioned and starts talking more easily, you know you're onto something.
Go on a group date with a small number of mutual friends--people your shy man knows and is comfortable with. Keep the excursion casual: dinner and a movie, bowling or a trip to a local amusement park. If it's not overwhelming and he's around people he knows, he'll start to open up with you. Subsequent dates can be more private as his comfort level grows.
- If you're comfortable, talk about mild concerns and fears with a shy guy. Many shy men are intimidated by women whom they perceive to be more worldly and sophisticated than they are. A small display of vulnerability--confessing a little nervousness or a slight insecurity--shows him that you're not someone to be placed on a pedestal.