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Establish eye contact. Glance from time to time at the person you are interested in, yet don’t overdo it. Smile when eyes connect. Feel out the emotional state of the other person to try and make them as comfortable as possible. Initiate the first move. Extend the first introduction and approach the shy person with a smile and a hello. Introduce yourself and start a simple, relaxed conversation. Be patient. During the conversation, give the shy person time to respond. Embrace silence — a meaningful pause can signal thoughtfulness and respect. Sometimes it takes time for a shy person to open up and get personal, so don’t rush the process. Attend to the shy person’s interests. Once you’ve revealed a few things that the shy person enjoys, direct the conversation toward these personal preferences, giving them more space to open up. End the conversation respectfully and positively. Especially in the first interaction, try to walk away feeling good about the meeting. Feel free to express how great the meeting was in a respectful and meaningful way, and that you are interested in meeting again. Invite the person to meet again. You don’t have to wait for the other person to reach out to you to go out. Make them aware that you are available and interested in meeting. Again, be proactive and ask them if they’d like to meet up sometime soon. Be direct about your interest in developing a friendship.