Here’s a quick difference between men and boys. Men take women out on dates. Boys want to “hang out.” Clearly, taking women out on dates is the superior move. Still, a lot of guys aren’t sure how to ask out a woman. It’s not something at which our generation excels. A lot of guys need a few pointers on how to do this the right way (and how to summon the courage to do it at all).


When you go out on a limb like this, you’re going to run the very real risk of getting totally shot down. That’s fine. The only people who never get shot down are people who never try.


Fortunately, giving men pointers on how to do things the right way is what I do for a living. So read on for six key steps to asking a girl out on a date, as well as an important bonus tip.

Step 1: Know What You Want to Do
Nothing is more annoying than having someone call to make plans without any idea of what they actually want to do. When you call a woman for a date, you need to have something to do. In fact, you need to have three things to do, because she might not like the first one. If you “pitch” her three and she’s not interested in any of them, you can be confident that she just doesn’t want to go out with you.

Step 2: Steel Yourself for Rejection
When you go out on a limb like this, you’re going to run the very real risk of getting totally shot down. That’s fine. The only people who never get shot down are people who never try to do anything. But you should be ready for that when you call. Hope for the best and plan for the worst, which in this case means that she’ll just say “no.”

Step 3: Call Her
On the phone. Don’t ask her out via text message or Facebook chat or whatever. You need to pick up your fancy-ass smartphone and actually dial her number. This shows that you’re a confident man, and it gives you a far better stance from which to ask for the date. Further, she’ll take you much more seriously than if you make plans via texting or G-chat. You’ll set this interaction apart from others, subtly making the point that she’s special enough to put in the effort of real-time communication.

This is no doubt what she’ll be wearing when you phone her up.

Step 4: Use the Word “Date”
Don’t ask her if she wants to hang out, get together or any other milquetoast euphemism. This isn’t any of that. That stuff was what you did back in high school and college when you were too scared to let your intentions be known. Now that you’re a man, you explicitly say what it is you’re going after.

Step 5: Be Casual
You’re asking her for a date, not her hand in marriage. Don’t make it a big deal. Call her up, engage in a little bit of banter, then ask for what you want as if it’s something that you do every day.

Step 6: Follow Up
You should follow up after you confirm the date. I don’t mean calling her every day between the day you ask and the night that you go out. I mean sending her a text message the day before mentioning that you’re looking forward to seeing her the next day. You can even do this in the course of other conversations, provided that you don’t lay it on too thick.

Bonus Tip: Have an Original Date
A lot of guys have trouble knowing what to do on a date. What makes for a good date varies from person to person, but as a rule, the obvious ones (coffee, dinner and a movie) are actually terrible first dates. Ditto on her coming by to hang out with you and your friends. There are five things a first date should be:

See, for her, rock climbing would be a good first-date activity.

>> Inexpensive: Don’t spend a ton of money trying to impress her.

>> Easy: It should be something that both of you can do without a lot of fuss. For some people hiking is easy. For others, it’s not.

>> Interactive: You want to be able to get to know her on the date. So it should offer ample opportunity for conversation. (This is why bowling, believe it or not, is better than a movie.)

>> One on One: Dates should never involve anyone but you and your date. No third, fourth or fifth wheels.

>> Controlled: You should have everything planned, but also be ready for deviations from that plan.

So there you have it. Now you know how to ask out a woman on a date, and what to do on it (see more tips in Score! Eight Great First Dates). Sure, it might be a little scary, but once you get two or three attempts out of the way, it will feel pretty natural. And it’s a skill you absolutely have to learn. Because if you’re tired of lingering in the friend zone, asking for a date like a man is your surest way out. Good luck!


Jordan Harbinger is a Wall Street lawyer turned Social Dynamics expert and coach. He is the owner and co-founder of The Art of Charm, a dating and relationships coaching company. If you dig this and want to learn more from Jordan and The Art of Charm team, visit You can also interact with Jordan on Facebook or Twitter.