Having a conversation with a shy person requires patience -- otherwise you may find that person retreating back into her shell. Loud conversations, abrasive comments and overly personal questions will leave a shy person feeling off kilter, while a sensitive and gentle approach will help make initial encounters go more smoothly. If you wish to help a shy person feel more comfortable, appreciate her sensitive nature and respect her need to go slowly -- especially in the beginning stages of a friendship or relationship.
People who are shy take longer to go through most of the developmental hurdles of life, according to Indiana University Southeast psychology professor Bernardo J. Carducci, Ph.D. For example, a shy man may take longer to start dating, marry or have children. Those who are shy may be out-of-step with acquaintances who have already moved past the life experiences that the shy person is just now experiencing. Help the shy person feel more comfortable by showing patience -- both by not pushing too soon for more than he can give in a relationship and understanding that your life experiences may be very different. For example, if a shy friend wants to talk about going on a first date, listen and show compassion for the obstacles that he facing, even if they seem insignificant to you.
Shyness involves a constant internal dialogue that tells the person he is "not good enough," asserts Carducci. The shy person might stand alone at a party, feeling that everyone else is judging her and that she is awkward and insignificant -- particularly in comparison to more outgoing and gregarious individuals. Your job is to make a shy person feel welcomed and "good enough" by offering genuine and sincere praise for those attributes and qualities that make her special to you. For example, tell an acquaintance how much you appreciate her ability to listen or her calm manner in the face of stress. When a shy person feels liked and welcomed by you, she will feel more comfortable.
Choose the Right Setting
Shy people can feel out of place in loud, bustling environments. If you really want to help a shy person feel more comfortable, suggest meeting in a quiet spot where the two of you can have a private conversation. A bookstore, quiet coffee shop or park bench is an ideal location to dive into getting to know a shy person better -- because he will feel more at ease. In contrast, a bar, nightclub or busy family gathering may leave a shy person feeling awkward and uncomfortable.
Find Mutual Interests
If you would really like to hit it off with a shy person, be the one to initiate small talk and search for topics of mutual interest, suggests Don Gabor, author of "Talking With Confidence for the Painfully Shy." For instance, ask your new friend what movies she has seen recently, what type of music she prefers or how she spends her free time. Take advantage of open-ended questions to find out her passions, and then compare them with your own hobbies and interests. Once you hit upon a subject of mutual interest, the shy person should feel more comfortable opening up and talking more freely. At that point you will have moved beyond small talk to having a genuine conversation.