How to Bring a Shy Guy out of His Shell

Building Confidence

Compliment him. Usually, compliments make people feel good and boost their self-esteem. If you notice something about the shy guy or something he is doing that you really like, give him a specific and sincere compliment. This should help him feel better about himself and also get communication going between you two, which will make talking to you a little easier for him. You might say something like: “I read your blog post last night about history class and it was so funny and well written! I can’t wait to read your next one.” Be careful not to overdo the effusiveness, which could make you seem fake.

Watch him in his element. If he plays soccer, go and watch him score a goal. If he plays the violin, attend his orchestra concert. When a shy guy is "in the zone," he will probably be happy to see you witness his strengths. He might not yet feel like he can be bold or straightforward around you, but he may feel empowered by seeing you in an environment where he’s successful and confident.

Chat via cell phone or social media. He might feel too intimidated and pressured to say the right thing face-to-face. He might feel more confident talking to you behind the safety of a phone or computer screen. Conversations online and through text message move a little slower, which will give him time to compose his thoughts and encourage him to open up.

Ask him for help. Men often feel more strong and masculine when they have the opportunity to help others. Ask him to fix your computer, your car, your bike, or anything else you think he might know how to fix. Helping you out will make him feel good, and he may even be more talkative in this kind of setting, so don’t hesitate to ask questions about the steps he’s taking to make the repair. Not all guys know how to fix things. Make sure that he’s knowledgeable about what you’re asking of him or else your plan may backfire and he might up feeling embarrassed.

Showing Interest

Ask open-ended questions. These kinds of questions can help a shy guy open up and talk about himself and can also lead to him feeling known, liked and comfortable with you. Avoid asking questions that can be answered with a quick “yes” or “no” because these may create awkward pauses and make the conversation feel forced. Good examples of open-ended questions include: "How did you get interested in carpentry?" "What brought you to live in San Francisco?"

Ask about his interests. When you ask about all of his favorite things, such as sports, movies, books, and more, you’re showing him that you’re interested in getting to know him better. Once you’ve talked a bit about each other's likes and dislikes, you’ll most likely find some commonalities that you can discuss further and bond over. Make sure to show interest in him and not just his role or activities. Hobbies and interests are good, neutral places to start, but when you're both ready, be sure to look deeper.

Be direct. If you hang out together, make sure to tell him you’d like to see him again when you part ways. Verbal clarity will make him more sure of your feelings and desires, which will ease his uncertainty and draw him out of his shell. Also, pay attention to his reactions when you say things that directly communicate your interest in him. If he smiles or agrees enthusiastically, you can assume that he may be interested in you too.

Make subtle physical contact if you like him. Making physical contact releases oxytocin, the bonding hormone, so initiating touch may quickly start making him feel liked and close to you. Touching him breaks through a kind of barrier that may lead him to feel less nervous or unsure about holding your hand or putting his arm around you later on. Ask permission first, and make sure he's open to that sort of attention and affection. Try lightly and briefly touching the outside of his arm to communicate assurance while you’re having a conversation with him. If you aren’t interested in him romantically, be cautious with physical contact. Giving him frequent hugs, for example, may seem friendly to you but he may interpret it as a romantic gesture.

Say his name often. People love to hear others say their own name because it brings a personal touch to an otherwise general situation or conversation. Not only will saying his name strengthen the bond between you and the shy guy, but it will also quicken the bonding process. You can also give him an endearing nickname to make him feel especially liked and noticed. If you give him a nickname, make sure that it’s positive and that he’s comfortable with being called that name.

Accepting Shyness

Adjust your expectations of change. The shy guy may not want to come out of his shell, and he may not share the same ideas of personal transformation that you do. Bringing a guy out of his shell is not an overnight process, but takes time. It’s not always as simple as being super kind or asking the right questions. You may need to help him build additional social skills, depending on his personal situation and experiences. It is best to consider that not only is this an investment on your part, but the shy guy must also put in a fair amount of invested work on their own as well. The most you can realistically hope for is that you can slowly chip away the shell that the shy guy has encased himself in. Be understanding and practice patience and acceptance.

Initiate and arrange plans. Shy guys often have a hard time reaching out to make plans because it makes them feel pressure and puts them in a vulnerable position. Save him the stress and just make the plans yourself. Try to cater to his comfortability by suggesting interaction that’s less communicative early on, such as going to see a movie together.

Be patient with him. He's not going to open up to you overnight, so don’t get frustrated if progress seems slow. Rushing may only intimidate him, so as your relationship grows, suggest the next move, but try to keep things at his pace. Building trust and comfort takes time. If you really want to show that you care for him, make it clear that you’re okay with that. He may seem awkward around you at first. Be persistent and compassionate.

Make the first move if you’re interested in him romantically. Don’t let your pride get in the way of making the first move. Especially if he’s really interested in you, it may come as a great relief to a guy who's a bit reserved if you ask him out or tell him you have feelings for him first. He may have really wanted to tell you, but his shyness just kept him from putting himself in a such a vulnerable position.