getting him to make the move

Reader T. M. writes:

I’ve been hanging out with a guy I like for a while and I think he likes me, but he won’t make a move. How can I get him to ask me out on an actual date or something?

Dear T.M.:

I think you have three options:

1. Wait forever.

2. Make the move yourself.

3. Move on to a guy who’s more aggressive.

In my experience, if a guy doesn’t make a move, it’s either because he’s too shy or he’s not interested. There’s a slight possibility he has no idea you’re interested, which is basically exactly like being too shy.

So what I’m thinking will happen is: nothing. Unless you make a move.

bigger man

Go on, be the bigger man. Image: graur codrin / FreeDigitalPhotos.net

While I am personally a greater fan of the guy making the first move (just like you, apparently), we actually live in an era where it’s always Sadie Hawkins time. Being slightly aggressive is no longer shunned or relegated to hussies and hos. Sack up them ovaries, tell him how you feel, and ask him if he feels the same way. Remember, rejection is good for you.

You can be coy about it and ask him why he hasn’t ever asked you on a date. Or you can be a real girl and straight up ask him to dinner, and make your intentions clear. Say to him, “I would like to date you. Are you interested?” He may be taken aback (particularly if he’s shy), but at least you’ll know whether he wants to date you or not.

You can try flirting harder, and giving him even broader hints that you want him to be romantic with you. Maybe he’s completely oblivious to your intentions. Guys can be strangely thick sometimes, especially if they lack a bit of confidence. But usually I find people who are oblivious are there because they want to be, and not because the other party isn’t being totally clear. He may not be attracted to you, and he may want your friendship to stay the way it is, and he may therefore be oblivious to your advances. This is why direct questioning is the best way to go. Get it out of the way.

You could also get a friend to tell him to ask you out. Then if there is rejection, it comes at you sideways (from your friend) rather than head-on (from his mouth). It’d be rather passive aggressive of you. It’d also be very seventh grade of you. And who didn’t love seventh grade? (That would be me; I hated seventh grade. Hence this option makes me roll my eyes. It’ll work, but it’s stupid.) (And maybe, technically, if he reads this blog, you’re basically doing the “have a friend tell him” thing through me. Damn, I’ve been caught in your web!)

Of course, moving on is probably my favorite option. If you’re not getting what you want, find someone else who will give it to you. We ladies always forget that you don’t have to be tied to anyone, especially not someone you’re not married to. You’re not even dating this guy yet. There are very likely some really nice crushable guys around you that will actually ask you out without needing to be instructed how. Find one of them and flirt away. If your current boy is actually interested, he may take up the competition and ask you out of his own volition. Or he may sneak away into the woodwork, in which case he’s not your type anyway.

The fact is, if you want a guy who will ask you out, this may not be the guy for you and you’re going to have to admit that. If you like this guy for who he is and want to date him, the ball is in your court.


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