Are you dealing with a guy that’s a bit shy and you’re wondering if he’s ever going to make a move? Here’s how to tell if you should buck up the courage to ask him out instead.
You know for a fact he’s shy. If his friends, family, or co-workers have confirmed to you that he’s a shy dude and doesn’t usually ask girls out, then this might be your clue to ask him out instead. It’s 2019, so go ahead and invite him out for coffee! You won’t regret it—the worst that can happen is he’ll say no, and then it would be his loss!
He asked you out in the past and you declined. If his ego is bruised from the past, he’s unlikely to try again. You might have to give him a little more confidence in order to get him to ask you out. Try being a bit more flirtatious or outright letting him know you like him. If that doesn’t work, go ahead and ask him for drinks! You already have evidence he likes you since he asked you out previously.
You’ve been acting like you don’t like him. If you’re playing hard to get by trying to act like you don’t like him, your plan may actually be backfiring. If he thinks you’ll say no, why would he ask you out? No one wants to sign up for rejection. Soften your game a little bit and flirt with him, girl!
He’s super focused. If he’s the brand of guy that is incredibly focused on his career, hobby, or finances, you might have to go out of your way a little bit to get him to notice you. This includes, just, you know, asking him out yourself.
You know he’s the type to play games. If you think he’s the one playing hard to get, then you might have to give in and be the one to make the first move here. If you aren’t the type to play games (and if you’re no longer in junior high, you shouldn’t be!), let him know. Tell him flat out you’re a straight-shooter, you don’t play games, and you would like to go out with him. How’s Saturday work for him?
He just got out of a serious relationship. This one’s a bit tricky. He may still be grieving or he may not even be thinking of dating yet. Feel it out a little bit and start slowly. Give him some time to process his own emotions and if it feels right, ask him out to do something low-key. Don’t put a lot of stress on it and manage your own expectations too.
You guys are good friends. He may not be willing to sacrifice his friendship with you, or he may not know how you feel about him. The first might not be something you can do anything about but the second is something you can.
You work together. This can always end awkwardly, so he may be worried that if things don’t work out, you’ll have to see each other every day at the office. He also may not know if he’s allowed to ask you out, so it might be good to double check your HR policies. If you get the green light, go ahead and let him know that you’d like to see him outside the office. If things don’t materialize for the two of you, you’re a professional and he has nothing to worry about.
He’s the “nice guy.” He may feel like he respects you a lot and thinks he’s in the friend zone. If he’s the guy that’s very nice, friends with a lot of girls, and might even get rejected a lot, you may have to let him know that you aren’t going to reject him.
You’re “out of his league.” If he isn’t someone you would traditionally date or isn’t your usual type, he might be picking up on this. Guys are usually pretty aware of their status within a hierarchy. If you usually date guys who are richer, more attractive, or taller, he may be nervous that he won’t measure up. This is the time to let him know how you feel—you have lots of types and your current type is HIM.
You’ve been known as a bit of a player. If you have a reputation for breaking hearts, he may be a little nervous to make the first move with you. After all, guys don’t want to get their hearts broken either. This is the time you’re going to have to go out on a limb.
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