If you’re trying to get closer to a shy acquaintance and develop a friendship, chances are that you’ll have to make the first move. Ask them if they’d like to meet up sometime soon, or send them a text asking if they’re busy. Be upfront about your interest in developing a friendship and, more likely than not, it will make them feel flattered and welcoming of your overtures.If you’re in school or college, it can be an easy, no-pressure invitation to ask if they would like to go get some coffee and study or go to a campus event.
If you know one another from work, see if they’d like to go out after work for a happy hour drink.
 Going out for a meal, drinks, or coffee is usually a good way to get to know someone, but these kinds of talk-heavy activities can be intimidating or high-pressure for a shy person. You can alleviate this pressure by planning activities for the first few times you hang out together: a shared activity means that neither of you has to work continuously to support the conversation. It will also create shared memories that deepen and strengthen a friendship.If you’re both sporty people, you can go for a hike or a bike ride. If one or both of you isn’t comfortable with this kind of activity, though, pick a more relaxed thing to do, such as seeing a movie or attending a community event.
 A shy person already knows they're shy, so mentioning and drawing further attention to it won’t do any good. In fact, you’ll just make the person feel uncomfortably spotlighted and even attacked for something which comes innately.You want to show them that you like and are interested in them just as they are, not that you’re trying to change them and their behavior in order to suit you.


For example, avoid saying things like, "You're so quiet! Why are you so quiet?" or "Stop being such a wallflower! Pipe up!" If you want to encourage your shy friend open up, say something instead like, "You always have such interesting stories, I'd love to hear more!"
If the shy person has done well by sustaining conversation for a while, give them a break. Take control of the conversation for a while or just keep the activities short and let them go.
 It can take time to break down the personal defense barriers of a shy person, so don’t rush the process. Keep talking points light and impersonal until you're well-acquainted. In general, this is good etiquette with anyone, but it’s particularly important when dealing with a shy person. Touching on a sensitive personal issue or political hot-button can make the shy person feel vulnerable and retreat back into their shell, effectively undoing any progress you’ve made in the past.


A good way to develop intimacy in a friendship is to divulge a secret or something personal from your life, or to acknowledge an insecurity of your own. This self-revealed vulnerability will make the shy person feel entrusted with your intimate feelings and more likely to share something personal with you in return.Revealing your own insecurity may make the shy person feel okay about their own anxieties.
Also be sure to avoid racy or dark humor. Racial, sexual, or extremely sarcastic jokes may offend the person or make them uncomfortable, so keep your banter breezy and PG-13.
 Introducing your friends to one another can be a tricky business with no established etiquette, and it's made even more difficult when you’re dealing with a shy person.Since it’s more difficult and takes longer to get to know a shy person, you might want to keep your hangout sessions one-on-one until you get more comfortable with one another. Letting other friends into the dynamic too soon can make the newcomer feel pushed out and more hesitant to open up, so wait a beat before you bring in the whole gang.


You can help facilitate this by telling this person about your friends before they meet — knowing what to expect can help them feel more comfortable.
Try introducing the person to others around you with a piece of information you learned about the person. For instance, “John have you met Allison? We were just talking about how much she loves traveling.” This will help the shy person make more connections and feel comfortable.
If you met the shy person through your larger group of friends, this is less of an issue. You should still make time for the two of you to hang out one-on-one, though, in order to cultivate a unique friendship.
 While a shy person will often open up after they begin feeling comfortable with a new acquaintance, they might revert to old, reserved ways when something bad happens or they’re struggling emotionally. Be a good friend by checking in and helping them to articulate these thoughts and feelings.


The best way to get anyone to open up is to show them you're listening. Pick a time when the two of you are alone and ask, "Hey, how have you been lately? What's been going on in your life?" If you've noticed your friend has seemed withdrawn or depressed, you can gently bring it up by saying, "It seems like you've been a bit down recently. Is there anything you want to talk about?"Make sure your friend knows that you're available and interested in the future as well. Reassure them by saying something like, "I'm always here to listen if you want to talk."
Invite the person to hang out.
Find activities you both enjoy.
Don’t tell the person to speak up.
Wait a while to get personal.
Introduce other friends gradually.
Check in to find out how the other person is feeling.
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