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Ask him to dance. Ask him out in a way that he won't realize it's a date. Include him in a group activity. Suggest attending an event that focuses on your shared interests. Find out what his interests are and suggest an outing related to them.
Many guys find it refreshing when girls take charge. If you're out and notice him looking at you, but not making a move, take matters into your own hands. Be flirty and suggest you dance together. He'll admire your confidence and liveliness. Try telling him that this is your favorite song to dance to, he might get the hint after that. Include him in a daily activity. If you have to run errands or are staying in to watch a movie, casually ask if he wants to join. There will be no pressure whatsoever, and he might not even realize that you technically were the one who asked him out. Reach out to him at the last minute, rather than planning in advance. This will make it seem more spontaneous. If you'd like to see more of him, invite him to a party or dance that your friends are all attending. This won't come off as too aggressive, but you'll still get a chance to get to know each other better. If he is too shy to ask you out, a group activity might be more his style anyway. It keeps the pressure off him and you'll be able to spend time together in a relaxed setting. He'll have a chance to see you interacting with the people you are most comfortable with, so your personality is sure to shine. This will not only emphasize what you have in common, but give you a perfectly good reason to ask him out. You'll have plenty to talk about on the date, because the event itself centers around a passion point for each of you. If you've talked about a band that you both listen to, suggest buying tickets to go together when they come to town. If you know that he also enjoys horror films, see if he'd like to go see the new scary movie that's out this weekend. He won't be able to refuse partaking in one of his favorite activities. Make sure you can at least carry a conversation about the particular topic. There's no need to pretend to be an expert, but he will be impressed that you are trying. Let him know that you have an extra ticket to the game this weekend if he'd like to go. Tell him you've been wanting to hit up the batting cages because you have a dreadful swing. He'll be able to let loose and be himself around you.