Muhammad Ali once said, "He who is not courageous enough to take risks will accomplish nothing in life." While asking a guy to hang out is not quite the same as stepping into the ring with a heavy-weight boxer, the fear in the pit of your stomach at the thought of looking foolish or being rejected may feel exactly the same. Like the boxing champion, however, you can put some strategies in place to make sure you're set to succeed.
Look to the Past
Reference something you've talked about earlier, recommends "Women's Health" columnist Christina Tudino. For example, if the two of you were chatting last week about his sunburn, text him a message asking him if he's gotten over it. In the ensuing discussion, ask him if he wants to hang at your neighborhood pool after getting a bite to eat at your house. Asking will feel much easier when it's part of a conversation you're already having than it will if you simply say, "Wanna hang out later" without any prelude -- although there's nothing wrong with that, either.
Focus His Attention
It will be easier to ask the guy you like to hang out if you know that you'll be getting the new version of an amazing video game the day before or otherwise have something to focus your -- and his -- attention on. Then you can walk up to him and say, "Hey, I just got an amazing new game -- wanna come over later and play it with me?" Or text him and let him know you just painted a mural in your room and that he should stop by and check it out.
If you're really having trouble working up the nerve to ask him over, invite a couple of friends and let them do the asking. Or say, "Hey, Greg and Sky are coming over later to shoot some pool, wanna come?" It'll likely calm your nerves to know that other people will be around to help carry the load of conversation. Then, when you're more comfortable with him, you can ask him to hang out when it will be just the two of you.
Plan what you want to say in advance, advises corporate communications consultant John Baldoni in an article in "Forbes." If you're planning to say, "Hey, wanna come over and watch movies?” Watch yourself in a mirror as you say those words. It may seem cheesy, but it works for actors preparing for a performance, and it can work for you when you're afraid you'll become tongue-tied in the presence of the guy you like.