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Shy guys may not feel comfortable making the first moves in a relationship. Instead of waiting for him to ask you out or to lean in first for a kiss, you make the first move. He may not feel comfortable taking the lead in these situations and you doing this will help take the pressure off him. Figuring out what to do on a date with a shy guy requires some thought. You'll need to make an effort to make him comfortable. Shy guys usually prefer low-key dates where they can relax and open up slowly over ones where they feel pressured to be outgoing. Opt for dates like staying in and watching a movie or spending an afternoon at the driving range, instead of inviting him out to a packed bar with a big group of friends. Dates that provide some kind of activity and don't focus solely on talking can help him relax. Dates on which he has the opportunity to teach you a skill he's good at are also a good idea. Not only will the two of you bond over the activity, but he'll likely get a boost of confidence by teaching you. When you're dealing with a shy guy, you will probably need to put in a majority of the effort needed to keep the conversation going. This can be tough when your guy isn't naturally chatty. To help encourage him to provide more than just a quick, one word answer, ask him open-ended questions and avoid those that can be answered with a "yes" or "no." For example, asking questions like, "How did you become such a great guitar player?" rather than, "Do you like playing the guitar?" will encourage him to share more details about himself. Although it might be easy for you to talk about what you like to do, a shy guy may have trouble adding to that conversation. Try talking about topics he's interested in and avoid topics that might make him uncomfortable, causing him to clam up. For instance, your guy probably won't have much to say about your recent experience at the nail salon, but he'll likely have quite a bit to say about the band you guys saw after dinner the other night. Talk about topics you both have in common. Also, remember to pick topics that won't make him feel uncomfortable. Asking him to talk about a strained family relationship, for instance, might cause him to become uncomfortable and stop talking. If you're having trouble getting him to open up in person, try using a different type of communication. For example, maybe he has trouble communicating in face-to-face situations, but feels more comfortable talking over the phone or texting. Give him the chance to do this until he starts to feel more comfortable around you. Social media platforms provide tons of different ways to communicate. Try messaging him on Facebook or Instagram to get the conversation going. Getting a shy guy to open up to you relies a great deal on building up his confidence. Make sure you let him know that you appreciate the little things he does for you. Praising him for things like taking out the trash, bringing you a coffee at work, and rubbing your feet at the end of a long day will let him know you are paying attention to his actions too, not just his words. This will help him feel loved and appreciated. Also be sure to praise him when he makes an effort to open up to you. If you had a great conversation one night, let him know how much you enjoyed it and that you'd like to hear more of his thoughts and ideas.
Make the first move. Plan dates where he can relax. Ask open-ended questions. Pick the right topic. Try different methods of communication. Praise his efforts.