How to Ask Someone Out


There’s one big secret, right in front of you.

When I was 19, a guy placed his hand on my cheek at a New Year’s Eve party and told me I was beautiful. He did that after about 20 minutes of flirting, to underscore his intentions.

It was a bold move —but it worked. Later that night we sat outside in the grass, holding hands and kissing.

The point of this story isn’t that you should walk up to girls and put your hand on their face and tell them they’re beautiful.

It’s something else:

There’s no single right way to ask someone out. There’s lots of ways — and only a few of them are wrong (because they’re illegal). Some suit your personality, and some don’t.

Dating apps have made everyone a little spoiled. We don’t invest anymore. We swipe. We think it makes dating easier.

But it doesn’t, not really.

It leads to swiping sickness. You look for love on your phone, when it could be right in front of you.

You rely on an algorithm to decide if you’re minimally compatible, and you wind up dehumanizing the most important step of a relationship — actually telling someone how you feel about them.

You put more thought into your connection to that person. If you’ve just met — you spend more time observing them, and listening. You have to make a decision, and a real commitment.

You have to deal with ambiguities, uncertainties, anticipation… You actually have to decide if the possibility of being with them is worth the hurt of hearing no. You have to summon confidence. And you have to make yourself vulnerable for a minute.

The word sure means something.

By comparison, swiping on someone is easy. You can swipe on 12 chicks in one night. Hey, dating apps work for lots of people. But they’ll never work for everyone. And if all you do is swipe-swipe-swipe, or wait to be swiped on, you’re taking a passive approach.

You’re missing out on the little nuances of human interaction that make a relationship in the first place.

When you swipe, you don’t really earn your first date. So you take it for granted. You almost waste it. You think, “If this doesn’t work out, there’s 23 other matches in my zip code.”

A date is more than an audition for sex.

There’s no such thing as an indirect approach. And yet, loads of guys (and girls) cling to it. Here’s the thing, you can’t trick someone into a date. Hiding your intentions just confuses things.

Almost anything counts as a date if you ask the right way. Don’t say, “Let’s meet up for coffee sometime.” You do that with work pals. If you want to go out with a girl, then say, “Can I take you out for coffee next Friday?” Or you say, “What are you doing this weekend?”

The direct approach doesn’t always get a direct answer. You have to deal with a polite dodge. If she tells you she’s busy and leaves it at that, she’s not playing hard to get. She’s not interested.

Maybe directness sounds a little dull. You’d rather establish a kind of rapport with someone first. You want to see how quick-witted they are. You want to see if your personalities match.

That’s fine — it’s why you flirt.

Everyone eventually flirts. All flirting comes down to is joking around with someone you want to have sex with. Some of us don’t really start flirting until midway through a date.

Others want to flirt before the date even starts.

It makes sense. When you joke with someone, you’re finding little ways to upset their expectations, which means you have to find out what those expectations are. You have to learn about them. Flirting is a fun way to build up to a date. If they joke back, it usually means they’re into you. If they don’t, then you should probably stop messing with them. They either don’t like you, or they’re not your type.

I’ve seen guys and girls ask someone out with barely a word. They see each other, and they just know.

They walk right up and hand you their phone number. They smile at you and hold your eyes on their way out the door.

You call them and set up a date — maybe coffee, or a drink. You either chat for a few minutes, or an hour. Great relationships start this way, even if they don’t always work out in the end.

The only wrong approach is one that makes you feel uncomfortable, or one that violates someone’s consent.

You never just ask someone out with your words — you do it with your eyes and face, and your shoulders.

Be inviting and confident, but not pushy. Just like you can’t trick someone into a date, you can’t intimidate or guilt anyone into one either. Some guys out there literally beg for love, or preemptively shame women for giving out fake phone numbers. That’s not cool.

A fake phone number or a lame excuse is the same thing as a no. It just means she was scared, and probably for a good reason.

Touching a girl’s face or hair after twenty minutes of conversation is about as bold as anyone should ever get.

If she doesn’t like it, she’ll let you know pretty quick. Don’t defend or justify yourself. Just apologize and leave her alone. Not every girl is a 19-year-old waiting to be swept off her feet on New Year’s Eve.

Maybe dating apps have killed the subtle art of asking someone out. But you can bring it back. It’ll be good for you.

Source : Medium