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Gentlemen Speak: What to Do When a Guy You Like Hasn’t Asked You Out Yet

How to know when it's time to take matters into your own hands.
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Photo Credit: Katie Ruther

I’m told that there are few things more frustrating to a single woman than a man who seems totally into you but has still not asked you out. What gives?

It’s likely that he is just not quite interested enough to make a move, but there is a chance your instincts are correct, and this guy is simply experiencing failure to launch. While I never claim to speak for all guys (and that’s especially true in this case), I find that it’s not always disinterest that keeps a guy at bay. That said, if you sit around waiting for him, you may never know.

Ladies, take it from a guy: It might be time to take matters into your own hands.

You don’t need to wallow in no-man-land (see what I did there?), as there are plenty of things a gal can do to bust out of the purgatory that is relational ambiguity. Here are a few ideas on how to get that date—or at least find out for sure if it’s time to move on.

Do a little reconnaissance.

You don’t want to be going into this blind. Pick out one of his buddies, and find out if there’s someone else. If so, how serious are they? Find out if he’s coming off a relationship or if there’s anything that might be keeping him from moving forward. Hell, while you’re at it, you could ask him point-blank: “Your buddy Romeo. Do you think he’s into me at all? Because I totally dig him.” This might be uncomfortable, but sometimes it pays to be direct (and trust me, Romeo’s friends won’t mind).

Ask him about his dating life.

This is a great way to find out what the heck is going on. Ask him if he has his eye on anyone in particular. If he says, “I can’t work up the guts to ask anybody out,” that might be encouraging. Maybe this means he likes you but is just scared. That also might be discouraging; do you really want to pursue a dude who can’t even ask a woman on a date? This approach can also serve to show him your interest. “Why do you ask?” he might say. “Oh, no reason . . .” you say, giving your best pregnant pause. Pay attention to how he responds in this situation. Personally, I get slightly uncomfortable talking about my dating life with someone I’m interested in.


This seems like a no-brainer, but let me tell you, Monica was not lying when she said it’s a lost art. One point I wholeheartedly agree with: Compliments go a long way. Especially in awkward group settings, a gal offering a little praise can be just the shot of confidence we need.

You see, as much as we’d like to fashion ourselves confident enough to approach any woman at any time, often a string of rejections is still too fresh in our minds. But if we know that someone of interest has already shown signs of intrigue—that’s a game changer.

This is just as important when you’re already friends as it is if you’re just meeting. One of the hardest calls for a dude is trying to figure out if a girl is being friendly because you’re friends or because she’s interested. Do what you can to make it clear that you’re flirting, not just being polite. P.S. Physical touch helps. A brief brush of the hand or light touch on the arm is where it’s at.

Meet him halfway.

Pretty much all men are deathly afraid of getting a no. If a guy seems a bit slow to ask for your number, and you want to give it to him, do yourselves both a favor by expediting the process.

This doesn’t mean you have to give him your number out of the blue, although that wouldn’t be the worst thing in the world. Sometimes men throw out comments to test the water. Remarks such as, “I would love to go to that concert,” are probably him kind of asking you out. So if you want to go out with him, say something like, “Well then, let’s go!” Or if he says, “I’d love to continue this conversation later,” you could say, “Let me give you my number,” or even, “How about this weekend?”

Tell him to ask you out on a date.

It’s a bit bold, of course, but that’s good. Men like bold. In fact, we love this sort of thing. It’s the best of both worlds, really. She clearly communicates what she wants to happen, with no room for misinterpretation, while still letting him have the honor of asking.

Keep things light and playful here, but hold his eye contact, and leave no room for doubt. What makes this approach even harder to resist is that you project a certain comfort level with your guy. It gives him a sense that you’re in this together. “Take my advice (smile, wink) because I want what’s best for you. Ask me out to dinner.” If you are having yet another great conversation about music or food, just throw it out there. “Well, you should take me some time.” If he is interested, he will jump at the chance.

Just ask him out on a date.

This isn’t every woman’s style, but if you are dying to know what his deal is, this is a surefire way to get an answer. The idea here is that the two of you have been spending enough time together that this wouldn’t come as a surprise. Sure, he might be embarrassed or disappointed that you beat him to the punch, but that’s his own fault. And he might decline. But then at least you know.

How should you do it? Think about what you would want. You don’t like ambiguity, so be clear. I personally like to use the word “date.” I want a date, so that’s what I ask for. Also, never apologize when you’re asking somebody out. Don’t say things like, “This might be weird,” or “I hope you aren’t creeped out by this.” Of course those things might be true, but saying it gives the guy a reason to think, “Yeah, this is weird,” instead of focusing on you. Besides, you wouldn’t want a guy to ask you out with caveats.

If you like a guy enough, and he hasn’t asked you out (and has missed his cues), what have you got to lose? Instead of sitting around frustrated and confused (or reading into every little thing he does or doesn’t do), you can get answers and save your energy for someone who is interested in return.