Use small talk to engage the shy person in light conversation. Although it's often perceived as a superficial approach to communication, small talk can be an effective way to help a shy person open up. Small talk doesn't just involve talking about the weather; skill is required to maintain the flow of conversation. Prepare relevant topics of conversation before calmly approaching the shy person. Use open-ended questions such as asking her opinion about a light topic and steer clear of controversial or otherwise "heavy" topics. Give her opportunities to respond. Smile and remain optimistic during the conversation to communicate a sense of warmth to the shy person.

Pay attention to nonverbal cues. Most communication is nonverbal; for a shy person, this can be his only means of communicating his feelings to you. Pay attention to your own nonverbal communication style, and avoid cues that can make a shy person feel anxious, such as prolonged eye contact. The book "Nonverbal Communication in Human Interaction" notes that eye contact can communicate what a shy person may not be able to verbalize. If you notice the person's eyes darting quickly away, then back to yours, it's a good sign that he finds you attractive. Allow the shy person to set the pace of nonverbal communication and try to mirror his physical behaviors to communicate an unstated solidarity.

Suggest activities you can enjoy together. For a shy person, it may be extremely difficult to take a step forward. Instead of waiting for a shy person to push past her fears, make a suggestion that you do something together. Don't use scenarios that suggest a "date," however, and instead consider activities such as going out to a movie with a group of friends. The presence of other people you both know can help buffer the shy person's anxiety and take the pressure off her to carry on a conversation with just one person. The goal is provide her with opportunities to get to know you.

Flirt with the shy person subtly rather than aggressively. Subtle flirting, explains the Social Issues Research Centre in its "Guide to Flirting," can be accomplished by simple things such as sitting close to the other person, smiling often, responding to what he says with enthusiasm and using the occasional compliment. The key is not to use all these approaches initially, which can cause a shy person to become anxious and defensive. Instead, gradually provide the shy person with subtle cues and pay attention to how he responds. Reduce the intensity or frequency of cues that appear to make the shy person more anxious.