How To Ask A Woman Out

Sure, there are guys out there who never seem to get shot down. But no matter what they tell you, asking a woman out is as much art as it is science.

Often, successfully asking a woman out comes down to that unquantifiable thing: mojo. Sometimes you’re feeling it, sometimes you’re not.

That said, there are a few guidelines that can increase your odds of success when asking a woman out on a date:


Don’t get too many steps ahead of yourself. You should be focusing on the moment and not flashing forward in your mind to a movie-montage of the love affair you’re going to have. Don’t get all dreamy about it—the higher your hopes and dreams are, the farther they can fall. For now, just focus on getting her to say yes to drinks on Friday.


It’s easy to make a big deal about how she’s going on a “date” with you. In your head you’re thinking, “She’s getting coffee with me. I’m IN!” Placing too much significance on the first date can make you seem a little desperate. It’s like if you went to a car lot and the salesperson said, “Hey, do you want to buy a car…from ME? Can I be your salesman?” You’d be creeped out. Much better if he casually said, “Hey, I’m Jim, do you want to do a test drive?” When asking a woman out, it’s better to think one date at a time. This isn’t a commitment to “go steady,” this is you getting to know each other better a couple hours at a time.


Ok, you know when I said you should avoid saying “date”? Well, I’d rather you say that than “hang out.” Your window of being able to ask women to “hang” closed right after you stopped riding a BMX bike. One of the biggest issues with asking a woman to hang out is that you’re not being clear about your intentions. At least if you ask a woman to dinner, she gets that it’s a date. But if you ask if she wants to “hang and play some X-Box,” who knows what she’ll think? You may even be putting yourself to the “friend zone” without realizing it. Now that you’re a man, ask her on a date.


Even if you’re nervous and you think there’s NO way she’s going to say yes, you need to be confident when you ask her out. If your body language and tone of voice say “You’re so much better than me, I’m a loser,” she might just believe it. Some guys understand this but take it too far—into swagger mode—and they come across like arrogant players. That’s where the nuance comes in: you need to strike a balance between acting like you KNOW she’s going to say yes, and not acting like a total douche. You can still be polite and act like you’re expecting a yes: look her in the eye, stand up straight, take your time and don’t fidget. After awhile, you’ll forget that you were “acting” confident and you’ll actually feel confident. And she’ll notice.


Literally: Wear nice shoes and you’re going to get the girl—that’s all there is to it. Of course I’m oversimplifying. It’s not just about the shoes…but there’s an element of truth to it. If you’re asking a woman out, you want to make sure your appearance is in top form. If you approach her in saggy sweatpants and a nappy old t-shirt, I’m not saying it’s a definite no, but you’re not helping your chances. Dress like you value yourself. Now back to the shoes: notice when you’re wearing a nice outfit, a woman’s eyes will go to your shoes. It’s amazing how great shoes can take a so-so outfit up to the next level. And just as often, a great outfit can be torpedoed by wearing crappy shoes. So, dress well and don’t forget the nice shoes.


If you go in there expecting she’ll say no, she probably will. Instead, envision success. Literally imagine what it will be like when she says yes. If you start imagining yourself getting nervous or tongue-tied, stop and start again until you imagine it going smoothly. Now the big caveat to this is: don’t get hung up rehearsing specific dialog—don’t memorize your script, otherwise if things veer off in a different direction you could really be thrown. Just envision the sensation of feeling success, of being confident, of having a good rapport with her. It’s not just about you, it’s about both of you enjoying a moment together.


Buddhists have a great attitude about attachment to the physical world. They have a phrase that goes something like “See the glass as already broken.” They don’t overreact when something is destroyed or when a glass breaks because that glass is already broken. It is inevitable that the glass will break, so they see the glass as already broken—there’s no overdeveloped sense of attachment to it. Asking a woman out should be the same. If she says no, it’s not like you’re really LOSING something. Instead of getting bent out of shape if she says no, just say to yourself, “ah well, her loss.” One thing the Buddhists won’t tell you is that asking women out is a numbers game. The more you get out there, the more you increase your chances of a woman saying yes. Once you realize that it takes 9 no’s to get to a yes, the no’s don’t sting as much.


Hopefully by the time you’re considering asking a woman out, you’ve already had some sort of conversation and made a connection.  It sounds silly, but lots of guys approach women in bars and ask for their number or ask them out right on the spot. That may work for guys who don’t care about personal chemistry. But I think you’ve got to make a connection first. Even if you’re SURE you’re in love before speaking two words to her, give it a chance to percolate by talking to her. If you ask her out too soon, you may get a no that would have been a yes if you’d just allowed the situation to develop. Sex needs foreplay and so does asking a woman out.


Don’t bring your baggage from other rejections into the conversation. The only person keeping score of your past “wins and losses” is you. It’s not like all the women who’ve ever known you set up a private Facebook page to discuss how to systematically ruin your life. They’re not in cahoots. Also, just because you got rejected last week doesn’t mean this new woman has to give you a break this week. Pity should not be in your arsenal. You still have to be confident and bring your A game.


You have to remember that what you’re doing is not a big deal. You’re not asking her to move in with you. You’re just asking her to spend a couple hours with you alone. Also, realize that whether a woman says yes or no, she respects you more for asking. At least you had the balls to try. And ultimately you realize that the initial fear you had is ridiculous. As you get older, you end up regretting the women you didn’t ask out, not the ones you did. So, suck it up and go for it.


Having one or two drinks before asking a girl out might be okay, but you really don’t need them. Be confident. You’ve got this. And by “got this” I just mean you’ll go through with it without peeing your pants. I can’t vouch for the outcome. The potential dangers of drinking too much before approaching a woman are pretty obvious: you could come across like a slurring, grabby douche. What’s funny is that many guys feel like they can only ask a woman out when they’ve had a few drinks so they can relax. But with practice, you’ll realize you can be just as relaxed and confident without the booze.


Just because she’s said yes doesn’t mean you can celebrate and ditch all pretenses. A yes certainly doesn’t give you permission to introduce her to your friends as your new squeeze or talk about how you’re going to go on a date. “Yeah brah, we’re totally going to Benihana together next Wednesday!” It’s also not usually a good idea to use the “post-yes” time to recap the “asking-out” segment of the evening: “Wow, I was pretty nervous, but I’m glad I asked you out. I didn’t think you were going to say yes. You’re purrrdy.” Just keep cool and enjoy the moment.


It’s easy to rationalize not asking or delaying asking a woman out because of various factors. Don’t let yourself wimp out. And don’t think you need a 5-part strategic plan. The more rigid and methodical you are about it, the creepier you’ll seem. Don’t delay, because sometimes the clock is ticking, especially if you’ve made a connection and the woman is expecting it. Writer Jeff Goins told a story about a girl in high school he’d been wanting to ask out for a while. When he finally got the cojones, he said it was a poor effort and he thought for sure he’d failed—he just mumbled something to her about going out. To his surprise she immediately said “I’d love to.” And then as she was walking away, she turned around and said “it’s about time.”



Real Weddings

Asaba James and Twinomujuni Deborah via mikolo