Summarize the following:
Instead of just awkwardly asking how it's going, try to have a more specific opening prepared to get the conversation flowing. Tell him what you're up to, ask about his plans for an upcoming event, or bring up an inside joke. Be sure to ask him open-ended questions that require more than a simple "yes" or "no."  For example, you might say, "I heard you're going to the Winter Formal with a group of your friends. Fun! What are you planning to wear?" You could also say something like, "I totally spaced when the homework assignment was announced in History. Can you help me out?" Light touches can help you gain the confidence to break the touch barrier in a more romantic way. For example, when you're talking to him, gently touch him on the arm when he says something funny, or "accidentally" bump into him when you're walking together. Everyone likes to be complimented, and it will also communicate that you're thinking of him. Focus on a quality you genuinely like about him⁠—whether it's his eyes, his sense of humor, his hair, and so on⁠—and tell him why you appreciate it. How you carry yourself can tell him a lot about how you feel! Plus, it will probably be a lot easier to move in for a kiss and, when you do, he won't be as surprised. Don't cross your arms, twiddle your thumbs, or clasp your hands together. Instead, orient your body toward him.  For example, if you're standing, keep your toes pointed at him. If you're sitting, point your knees. If you can't help fidgeting, put your hands behind your back so that you look open from the front. You don't have to be totally alone, but a little privacy is ideal. For example, if you're hanging out with a group, go outside to grab some fresh air with him. If you're hanging out in public, try to find a quiet area that feels intimate. For instance, if you're at the mall, you could sit on a bench in a low-traffic area.  You could also try offering to walk home with him or dropping by his house to ask if he'd like to go out for a bit. If you really want to make sure you're alone, you can always ask him out on a solo date. Kissing him will feel more natural if you gradually move a little closer to him. It will also subtly alert him that you want to be intimate, which is always better than swooping in suddenly and completely catching him off guard.  If you're sitting together on a couch or in a car, move in closer than you need to. If you're standing up, inch a little closer to him or visibly shiver to see if he pulls you close. You can also try holding his hand or leaning on his shoulder. This usually works best when you're leaving or parting ways, but you can try it any time, like when you're snuggling and watching movies. Lean in close to him, put your arms around his neck or shoulders, and hold the embrace for 2-3 seconds before pulling away. You want to create an intimate moment, but don't hug him for so long that it gets awkward!
Say "hi" when you see him and strike up a conversation. Find excuses to touch him in small, fleeting ways. Pay him a genuine compliment. Keep your body language positive and open. Find a good opportunity to be alone with him. Sit or stand a little closer to him. Go in for a hug or snuggle to initiate a romantic moment.