The Approach
Walk slowly toward the shy person, in a non-threatening matter. Make sure to come alone, as a big group of people can seem intimidating, especially to a socially awkward person.
Greet the person with a smile, and a friendly 'Hello." Most people will answer back.
Be genuine in your wish to get to know the shy person. You don't want to make the person feel like you are befriending them only out of pity. They may be quiet, but most likely they aren't stupid. Pretending to be nice will only embarrass them, and make them harder to talk to.
Conversing Together
Be prepared to be the one who starts the conversation. Most likely this will be essential. When asking questions, be sure not to get too personal, as this will cause the shy person to feel uncomfortable, and may make you seem nosy. A good question would be "Did you hear it was supposed to rain today" or "Did you understand the math homework?" When talking, be sure to not make eye contact. This can seem intimidating to most shy people. Unless they make eye contact with you, don't do it back. Getting to know a shy person is similar to knowing someone who is not shy. The only difference is that you may have to ask more questions or lead the conversation more. Ask questions, express interest, go slow, and don't interrupt them. If they are already shy and you jump in with your comments, they may not feel confident enough to talk to you.
Make sure to keep a warm smile at all times. This will help you to avoid creating tension and helps the person feel safe. Talk in a light voice, but make sure to talk loudly enough so that you can be heard clearly. When talking to a shy person, make sure to never draw attention to their shyness. Most people would take this as an insult, especially if they don't know you well. Questions like 'Why are you so shy?" or "Speak up!" will only make them draw farther away from you.
Getting to Know Each Other Better
Avoid getting involved with the shy person's social media until you get to know them better. After a couple of weeks, or whenever you feel they are ready, you can ask for their phone number.
Make up a nickname. This can be a good way to bond. Be careful to make sure that the name is not offensive though. A name such as "Em" for a girl named Emily, would be suitable. Do not overuse the nickname; that could begin to be annoying, especially if they aren't as fond of it as you are.
Take your time. Bonding with a shy person could take from just a few days, to even a few months, depending on how shy the person is. Never rush anything, and never make it seem like a "Project." If the person finds out, most likely they will be hurt
Expand your friendship. Find ways to help your shy friend meet other people or get out and do things together. Once you feel you have a good relationship with the person, try introducing some of your close friends. Only do this when you are both good friends though, for if this is done too soon, the person will likely feel very uncomfortable. Asking to do things outside of the place you met in, whether it be work, school, art class etc is a big step. This could either strengthen your bond or break it. Make sure that your relationship is strong enough. Asking the person before they are ready could make them feel helpless and uncomfortable.
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