Shy men need to know that you like them. Although you might think that your feelings are obvious, a shy guy is more apt to question your view of him, because his own self-view is often negative and critical. Shy individuals spend a good deal of time thinking badly about themselves, asserts Carducci. One way to let a shy man know how you feel would be to offer a compliment, recommends the Shyness Research Institute. Tell him how much you enjoy his stories, how his smile lights up the room or how comfortable you feel in his presence. A few complimentary words will go a long way toward reassuring the shy man that you want to get to know him better.

A loud party or disco night club might be a good spot to hang out with adventurous friends -- but they are not the ideal locations to get a shy man to open up. If you want to help a shy man start talking, choose a quiet spot where the two of you can talk one-on-one. If you want to accelerate the comfort level even more, consider connecting through electronic communication such as chat, email or text. Carducci notes that shy individuals are more likely to open up when chatting through electronic means, as they are able to take time when formulating responses and may feel more comfortable than when talking in person.

Approach a conversation with a shy man using a bit of caution. On Match.com, psychologist Laurie Helgoe recommends choosing topics that are light, such as music, movies and food, and staying away from heavier subjects such as politics and religion -- at least until you get to know one another better. Helgoe takes this advice a step further, advocating against sharing too much personal information about yourself when initially talking to a shy person; also, ensure you hold in confidence anything that he tells you about himself. Be discreet, be considerate and show the shy guy that he can trust you. Displaying these qualities will make it easier for him to open up.

More than anything, a shy man needs time to open up. Rather than beginning an interrogation session, wait until he is feeling comfortable with you and gradually encourage him to share more about himself. Shy individuals are slow to warm up to new situations and need more time to adjust, warns Carducci. Be patient with a shy man and understand that he will not immediately feel comfortable sharing details about himself. As you get to know each other better, ask him open-ended questions to learn more about what he enjoys and dislikes. Show a genuine interest combined with a patient attitude, and he will eventually feel comfortable enough to divulge his most personal thoughts.