How to Get a Shy Guy
If you have a crush on a shy guy, don't wait for him to ask you out or make a move. Instead, catch his attention by smiling at him during class or making eye contact with him during lunchtime. To strike up a conversation with your shy guy, try some casual comments about class or vaction plans. When you're talking to him, give him a light touch on the arm or a pat on the shoulder every so often to hint at your romantic interest. As you become more comfortable together, ask for his number by saying something like “Hey, I've liked talking to you for the last few weeks. It would be fun if we could talk more. Could I get your number?” Then, try to text or call him a few times a week to let him know you're interested in being more than casual friends.
Smile and hold eye contact from across a room. If you don't know the shy guy you're interested in, start to catch his attention with subtle moves. Try smiling at him during class or over lunch, and make eye contact for 2 or 3 seconds before looking away. You never know, maybe the guy has had his eye on you for a while too. If that's the case, your open, engaging behavior may give him a needed confidence-boost and lead to conversations and dates. Make light physical contact to show your interest. Physical touch can indicate personal, romantic interest. A touch on the arm or pat on the shoulder is fine. However, if he seems fine with it, then you should continue to do it every once in a while. As the 2 of you get to know each other a little better, try giving him hugs or touching his hand to get his attention. If the guy recoils when you touch him, lay off of physical touch for a couple weeks. He may warm up to the idea more once you two know each other better. Contact him on a social network. If the guy has a Facebook, Instagram, or Twitter account, follow his page and leave a few “likes” and comments. This won't come across as overbearing or intimidating, and will give him a chance to think about his reply to your post. You can even “Like” a few of his pictures, and leave a slightly flirty comment on one or two of them. Find a picture in which he looks good, and comment something like “Wow! You look amazing,” or “I wish I'd been there with you!” Strike up a casual conversation with the guy. Small talk is usually rather impersonal and can consist of topics like: the homework, weather, teachers, vacation plans, or something on the news. If you don't go to school with him, maybe ask what he likes to do other than homework, and school. If the conversation goes well, try talking to him again later in the week. Say something like, “Hi, I think we're in the same Physics class! What did you think of that homework last night? It took me several hours.” Don't worry if you're doing most of the talking for the first few conversations. It might take the guy a few conversations to start opening up to you. Ask for the guy’s number. A direct approach is best; don't try to play games or to get his number from somebody else. Getting his phone number is a flirty move that will let him know you're interested in him as a potential romantic partner. It will also allow the 2 of you to have more drawn-out conversations. Say something like, “Hey, I've enjoyed talking to you at school for the past couple of weeks. It'd be fun if we could keep the conversation going when we're not together; could I get your number?” Remember, if he doesn't text you first, don't sweat it. If he's shy in person with you, he'll be shy over text at first too! Attempt to talk to him a few times a week. By talking to him a few times a week, you will begin to establish a bond and let him know that you're interested in being more than an occasional conversation partner. Until he opens up to you fully, try to lead the conversation by asking him questions. This will encourage him to talk more and even confide in you. Ask things like: “My family and I usually take a trip up to Aspen every winter. Do you travel often with your family?” “I like your shirt; The Ramones are a great band. Do you have a favorite record by them?” Ask him out for a date. Asking him out is a great way to move things to the next level, and it'll also let him know unequivocally where you stand regarding the relationship. Make sure to ask him out in private so that the guy doesn't feel nervous. Shy people can be very protective of their emotions, and he may hate feeling pressured. Say something like, “You know, I like being around you, and it's been fun to get to know you better. Would you like to go out on a date sometime?” “I'm attracted to you and I'd like it if we could spend more time together. Can we go out sometime; we could get coffee or see a movie?” Suggest an activity that you know he’ll enjoy. The shy guy may not have a lot of personal confidence, or may need engaging activities to help bring him out of his shell. In either case, try to find an activity or environment that you'll both feel comfortable and at-ease in. Go to a volunteering event together, or have lunch at a café nearby. Make sure that you'll enjoy the date too! If the guy loves mini golf but you can't stand it, find a different activity. Hang out with the guy in social settings. Just because the guy you're interested in is shy doesn't mean that he's a social recluse. So, throw a small party and invite a few people you know he'll be comfortable with. Make it fun by trying some ice-breaking games and a bottle of wine (if you're all over 21). Or, invite the guy to meet a few of your friends at a coffee shop or an art museum. If the guy likes movies, invite him to see a movie with you and a couple friends. Keep the first few hang-outs low-key. Fancy, extravagant dates can lead to high-pressure, uncomfortable situations, especially for a shy guy. The good news is that there are plenty of ways for the 2 of you to spend time together doing things that aren't stereotypical dates. Take hikes or go cycling together, do a fun bar-hop on a weekday evening, or go sledding in winter. For example, maybe going out to public places is not his thing. Suggest a movie at your house or something else that's low-key. You could also suggest getting drive-through dinner and parking someplace quiet to eat and talk. During your time together, listen to what he says so that you can get a feel for what he's comfortable doing. For example, if he says loud places make him uncomfortable, then you'll know not to invite him to a concert. 
Smile and hold eye contact from across a room. Make light physical contact to show your interest. Contact him on a social network. Strike up a casual conversation with the guy. Ask for the guy’s number. Attempt to talk to him a few times a week. Ask him out for a date. Suggest an activity that you know he’ll enjoy. Hang out with the guy in social settings. Keep the first few hang-outs low-key. 