Seek out a shy guy when he's in his element or doing something he enjoys, such as playing pool or jogging. Chances are that he'll feel confident at the time and be less skittish. If he seems flustered or preoccupied by another activity or person, approach him later, when he doesn't seem overwhelmed.
Touch his arm briefly; introduce yourself and ask him a question that will break the ice between the two of you. Ask a question that requires more than a "yes" or "no" answer for best results. For example, "What do you think of the new gym that just opened?"
Address him using his name in order to make a connection with him, instead of addressing him indirectly. If, during your conversation, you come with a playful nickname, don't be afraid to use it from time to time. For example, if he's from the country, call him "Cowboy." This will help you inject a bit of humor into the encounter.
Ask him more open-ended questions to keep the conversation alive. If you find something you have in common, suggest getting together. For example, if you ask him what type of movies he enjoys and he tells you he likes films with action, ask him if he wants to check out the latest action movie at the theater.
Give him a sincere compliment to make him feel good. For instance, if he seems to know a lot about a certain topic, tell him you're impressed with his knowledge on the subject.
- Ask him about favorite foods, hobbies or sports to find out more about his likes and discover a common interest.
- Don't be discouraged if a shy guy doesn't seem that into you at first. Keep trying and maybe he will open up.