How to Flirt

Flirting is, in my experience, something of a lost art, especially amongst nerds. They simply don’t understand how to flirt. Too many young nerds have hit some sort of mystical, magical combination of bad influences that seems to have convinced them to make all the wrong moves. It seems to be split into the camp that believes that to get the girl you have to either be intensely sincere to the point of being creepy  and the camp that is so nice and obliging that they may as well tattoo “WELCOME” on their backs and resign themselves to a career of women wiping their shoes on them.

Personally, I blame John Hughes.

But hey. You want to learn how to flirt and clearly many people have gotten the wrong impressions so let’s start off with what it’s not: 

Flirting isn’t complicated.
Flirting isn’t a wide variety of subtle signals you have to keep an eagle-eye out for.
Flirting isn’t intense.
Flirting isn’t making fun of people, “negging” or generally being an asshole.

All well and good, yes?

So let’s move on to what it is and how to flirt.

Flirting is, at it’s core, a way to engage, size up and generate attraction in a perspective mate. It’s light and it’s friendly. It’s a combination of banter, body language and teasing.

Let’s start by watching this clip of Matt Damon and Emily Blunt from The Adjustment Bureau:

So, clearly, flirting is like acting like a couple of six year olds who snipe at each other and screw around with the other’s personal possessions.

Or, y’know, not. But this is one of the best and most realistic flirting scenes you can find in modern cinema (and, critically, that I could find on YouTube). As you watch the two of them, you can tell that they’re starting to like each other, even as they insult each other’s fashion sense and she destroys his Blackberry. But why does this work?

Let’s break it down. Flirting really comes down to a three key points:


Teasing, put simply, is the art of saying something mean that really means “I like you”. Flirting is essentially teasing with intent. It’s banter;  a playful back-and-forth between two people. It’s fun and inclusive and a little silly, and when done right, it’s incredibly attractive.

There’s a certain structure to teasing as flirting; in another context it could look like a couple verbally jousting for social dominance. The keys are tone of voice and to be careful not to make the teasing too harsh. An easy short-hand to teasing is to imagine the other person as your bratty little sister; you’re needling at them for a reaction rather tan trying to actually insult them. As you’re teasing, you can incorporate a number of ideas. You can start a role-play, establishing some sort of ridiculous fantasy situation; if she talks about a love of cooking or food, you can say “Hey, you can totally be my personal chef. I’m going to have you make all these insanely elaborate meals for me.” If she’s clumsy or drops something, “Wow, you’re officially the worst personal assistant I’ve ever had. It’s bad enough you wear these inappropriate outfits around the office, but this is the final straw.” “That’s it. We’re totally breaking up. Give me back my CDs and I’m keeping the dog.” Think of it like an improv exercise, especially if she teases you in this manner; the response is should be”Yes, and…”, extending the scenario.

Challenging is also an important part of teasing and flirting. Too many nerds have Chronic Nice Guy syndrome, and won’t stand up for themselves when a woman gives them shit; a teasing challenge is a playful indicator of some spine as well as bait into being more aggressive. Challenges work on the same part of the contrarian part of human psychology; by telling someone they can’t have, be or do something, the first impuse is “Yeah, I totally can”. You can challenge in any number of ways; you can call her a name: “Dork”, “Princess”, “Brat”, “Crazy”. Challenges can be a miniature cold-read, giving them an opening to open up about themselves: “I bet you must drive your parents crazy.” “You can’t be from around here; you must be a West Coast girl. I can always tell.” It can be physical: “OK, obviously we’re going to need to settle this in the manner of our ancestors: thumb-wrestling. And I should warn you, I’m totally the thumb-wrestling champion of the Eastern seaboard.” It can have a certain sexual edge to it to raise the heat:”Your last boyfriend just didn’t spank you enough, huh?” “Don’t make me come down there little girl, I’d eat you for breakfast”.

A rule of thumb is that if she’s not laughing, agreeing with you, playing along or playfully disagreeing, then you’re doing something wrong. Dial it back a notch until you figure out what you did wrong, then calibrate accordingly.

Pushing And Pulling

The human psyche is perverse; we wan’t what we can’t have. We instinctively chase what runs from us. When things come too easily, we question it or take it for granted, but we value the things we had to work for. And we find unpredictability attractive. It gets boring and we don’t want it around. The idea of pushing and pulling is to deliberately send mixed signals… “Go away a little closer”, in essence. They keep people on their toes, because they don’t know what comes next.

Pushing and pulling in a flirting context is a matter of balance; giving something and taking it away at the same time. It’s a teasing insult followed by a compliment, or a compliment followed by a disqualifier. The effect is a little like a kitten with a string; you dangle the complement within reach, then pull it back. End result: the kitten becomes more determined to catch the string. So it goes with flirting.

“You’re the coolest person I’ve met… at this bar, anyway.” “Holy crap, you really are such a nerd, it’s adorable!” “It’s a shame you seem like a nice person, you’re giving me the most inappropriate ideas.” “You’re awesome, I never meet people like you; get away from me, I just can’t talk to you.” “We’re never going to get along, we’re too similar.”

This isn’t “negging” or backhanded compliments. You don’t want to say things like “You’ve got a great smile… even with those teeth,” “Your nails are great… are they real?”  Much like with teasing, it’s something that’s supposed to be playful and friendly. A balance needs to be maintained… too complimentary and you become boring. Too much in the other direction and you’re being an asshole. A number of people may need to practice their calibration before they get the balance just right. If you’ve found that you’ve inadvertently offended someone, apologize and offer a sincere compliment, and dial the disqualifications back in intensity.

Body Language

I’ve talked about body language and it’s importance, and it’s especially relevant here. Part of the way you keep the name-calling and playful insults from being interpreted as real insults is via body language. Large, friendly smiles, a light tone of voice and open body positioning (uncrossed, arms, facing them full-on) and a relaxed posture all give the feeling of friendliness even when you’re calling her a brat. Your eyes are an important part of flirting as well. Your eyes can send any number of signals. If you meet eyes with a woman, who returns your look, looks away then looks back, she’s interested in talking to you. A well-timed roll of the eyes can work as well as a teasing disqualifier when pushing and pulling. Holding eye contact for longer than a glance, then deliberately breaking it before making the other person uncomfortable is an incredibly powerful move that builds a certain sense of excitement.

Body language is also important in teasing and pushing and pulling.  Touch on the arm or the shoulder during a high emotional point in a story or a role-play for emphasis. You can give a playful (and gentle!) literal push on the shoulder with a disqualifier. “Oh god, you’re awesome, get away from me <push>”

In general, you want to use less movement and get rid of nervous twitches and shifting. However, you can use a sort of body rock to emphasize the disqualification.  As an example, using a push-pull, you say something along the lines of”Oh man, what am I going to do with you?” with a smile and a touch on the shoulder. Followed up with  “Don’t make me think things like this, they’re inappropriate right now,”  as you pivot slightly on one foot and step back with the other, as though you are getting ready to walk away. Then you step back to your initial stance and continue the conversation.

Now that we’ve broken things down, watch that clip again and see how these concepts apply to Damon and Blunt’s bantering on the bus. Flirting is a skill and it takes calibration and  practice, but once you understand the underlying concepts, it’s remarkably simple and effective.