How to Ask A Girl Out (Or a Boy, or Anyone)


If you’re wondering how to ask a girl out, it’s a good question: We’re past sixth grade. You no longer get to ask your buddy Tommy to ask your crush out for you. Now it’s your responsibility to ask people on dates!

Maybe you’re a magically self-assured person for whom this isn’t difficult. If so, congratulations! For most of us, no matter your gender or who you’re interested in dating, asking someone out is mildly terrifying. It’s asking someone to agree that you’re not a romantically repulsive person. It’s setting yourself up for potential rejection.

But also…it’s really not a big deal. And the more you treat it that way, the better your odds of getting a yes.

The Idea Is to Seem Like You’re a Good Time to Hang Out With.

You do not need to rush and ambush someone before another guy gets to them—you need to demonstrate to someone that you are a chill, normal person, and that you see them as another person, and not just someone you saw across the dentist’s waiting room whom you’d like to see naked. Talk to that person a little before asking them out. You should know their name and at least two other things about them before you ask. (Job, hometown, that they hate tequila shots, that it’s their friend’s birthday, etc). If you’re in a situation where that conversation is not going to happen, it’s probably not the time to shoot your shot.

Know that you have the power to set the tone when asking someone out. If you treat it like it’s no big deal, that you’re simply interested in the person and would like to get to know them better, you’re a lot, lot, lot more likely to get someone to agree to a date. Why? Because the stakes are low for them. Because you haven’t made it seem like you might freak out if they say no. By being calm and moving slowly, you’ve displayed a lot more quiet confidence than chasing desperately after people or, god forbid, following them around the bar. Instead, you’ve made it seem like a good time to hang out with—which is your goal.

Be Specific.

If you’re old enough to be forklift certified, you are old enough to ask someone out on a specific, thought out date. I’m not saying you need to email an itinerary. I’m just saying do not ask, “Are you free sometime?”

Not only is a vague date request difficult to turn down if the other person actually doesn’t like you—what are they going to say: “I am never, ever going to be free”?—but vagueness also doesn’t properly demonstrate interest or effort. If you think you’re too cool to convey interest in a person, you’re not ready to date. (“We should get coffee sometime,” is something I have said to ex-coworkers I have loathed.)

“Hey, do you want to get drinks on Thursday?” might work. Or “Are you free next week for dinner? I’ve been looking for a reason to try [INSERT APPEALING RESTAURANT IN YOUR CITY HERE]” could be the ticket. You want to be clear on what is happening and give the person you’re asking room to actually communicate truthfully.

Here’s A Date Hack to Try:

I’m going to give you one of the best tricks there is: Invite other people along to things you’re (at least allegedly) already going to do.



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