How to Improve at Flirting When You Don’t Like Flirting

have fun git gud

Welcome to algebra class. Today we will prove the central theorem of flirting.

Lemma 1 — To enjoy flirting, you must be good at it. Nothing feels as good as successful seduction, or as bad as rejection. It’s hard to enjoy the process when so much is at stake with the outcome.

Lemma 2 — To get good at flirting, you must practice. No one was born smooth and confident. Flirting is an anti-inductive game with an ever-evolving meta, you need to constantly improve just to keep up.

Lemma 3 — To practice flirting, you must enjoy it. It’s attractive to be confident, relaxed, and optimistic. If you’re forcing yourself to flirt through gritted teeth, people can tell. And why would you even force yourself to do something you hate?

Conclusion: if you’re not already good, practiced, and having fun flirting, you never will be since either one requires the others. You’re in a catch-22 with no chicken and no egg. 1+2+3 = QED.

Fix Mindset

Just kidding, friends, just kidding. But before we attack the conclusion, let me actually offer some support for the lemmas.

The counterargument — there’s no such thing as “getting good through practice”. Your success in flirting is determined before you even start, through some combination of innate traits (looks, charisma), persistent attributes (fitness, career success), or sheer luck (meeting your soulmate). “Practice” sounds like some pick-up artist bullshit to trick girls, but you can’t fool anyone for long anyway. If it’s meant to be it’s meant to be. And if it isn’t, you can’t help it.

There’s a lot of truth to this. Looks matter, stable traits matter, a relationship won’t hold for long on the strength of practiced flirting alone. But this argument is missing two important things.

First: the fixed mindset implicitly assumes that we each have our “dateability ELO”, our ranking on the ladder of all other daters. Since that ranking is mostly set by universally-desired traits (looks, youth, success), flirting practice won’t move you up the ranks. I call this the “Sexual Marketplace Value fallacy”.

We’re all looking for a combination of universal desiderata and our own special compatibilities. If you’re a homebody, you might want a partner who isn’t very outgoing so you can enjoy cozy time together. But perhaps you want someone who is adventurous to help you out of your shell. A wild spirit may be looking for someone to match their vibe or for a grounding presence. “Adventurousness” isn’t universally high-SMV or low-SMV, it depends on context and on the person looking.

The point of flirting is everything aside from SMV. People can judge your looks, age, and social class the moment you walk in the room. But they don’t know if you prefer mountaineering or quilting, if you’re a quiet listener or a gregarious storyteller, if you care about sports or literature. Flirting is how you show what’s unique about you, not what’s universally appealing. And it’s how you discover what’s unique about the person you’re flirting with.

Second: if it’s meant to be it still probably won’t, because the default outcome is nothing. Unless you’re literally being sold into marriage for a dowry of camels, there’s no one who is so “meant for you” that you can end up together without flirting. (You may be longtime friends and not even realize that you’ve been flirting for a year, but that too is a skill!) You get a lot of information “at first sight”, but love requires talking to the other person.

Many people are tired of apps and mixers and dream about meeting the love of their life as their hands serendipitously brush while reaching for the last sleeve of Mentos at the grocery checkout line. I’m not saying it won’t happen to you. But at that moment, wouldn’t you wish that you had practiced the art of striking a flirty conversation about Mentos?

There’s a lot more to flirting than pick-up lines and coy smiles. From spotting the right person to making a graceful exit. From maintaining good eye contact to maintaining plausible deniability. From following up on successes to recovering from rejections. You don’t improve these skills just by SMV-maxxing on your own.

But this is also what can make it feel overwhelming. There are so many aspects of flirting to potentially suck and fail at, and success is often out of your control. “Growth mindset” is often contorted into “everyone can be a champion” which is A: plainly false, and B: pointlessly recasts a collaborative endeavor as a competition. You’re not going to beat everybody at flirting. But if your goal is just to meet somebody, practice helps.

Started from the Bottom now I’m Top 20%

This post doesn’t really fit in the current chapter, but I was inspired to write it by SCPantera’s essay The Skill Issue Issue. Here’s a snippet:

I can’t recall where I first encountered the “passion” component but I think it was in relation to fighting games. The idea here being that a top player will have spent hundreds or maybe thousands of hours in a game’s practice mode perfecting combos and pouring over frame data, optimizing offensive and defensive strategies, testing what works in a punish counter situation, practicing hit confirms and reactions, etc etc. If you have ever tried to do this yourself, you might know that this is skull-crushingly dull and frankly pretty unbearable to do for even just a few minutes, especially compared to the tense, exciting action of simply playing the game normally.

The most unpleasant truth is that getting really good at something requires both some amount of innate baseline talent and an unusual passion for the thing that makes the overwhelmingly boring process of improvement at the thing unintuitively fun and rewarding.

This was part of an amusing exchange between Axel and SCPantera in the comments on my last post. Axel sees dating as a matter of setting standards and evaluating criteria, a frame that can’t really make sense of polyamory. SCPantera replied: it’s not about my standards, it’s about my love of the game.

Here’s an incredible comment I got on a an old dating post I wrote:

It prompted me to share some of my experiences with girls in my younger years. These experiences included: getting slapped, getting body-shamed, getting stood up, getting cheated at tennis, having my birthday cake eaten. Combined, they did absolutely nothing to diminish my love of the game. I kept thinking about girls, flirting with girls, and enjoying their company when I could. I’m fairly certain this is the main reason for what dating success I’ve had in my 30s, not my ethnicity or military experience.

The main goal of Second Person is to infect you with my love of the game of dating. To help you see through the confusion, ignore the negativity, follow a positive vision, and actually go out there and try stuff. I can’t convince you into an attitude change with arguments, but I hope a little of it rubs off on you with every essay you spend in my company.

What if you hate every single thing about dating? You should start here. Come back to flirting when you’ve transmuted at least some of your resentment into curiosity.

What if you hate almost every single thing about it? Then it means there’s something you don’t hate. You can start from this kernel of enjoyment and practice some flirt-relevant competency, slowly expanding your practice and your enjoyment to adjacent skills.

That’s the good thing about chicken and egg problems: you only need one thing to get the whole cycle going.

10 Ways to Git Gud at Flirting by Doing Things You May Already Enjoy Doing

(Are we seriously doing a numbered advice listicle? LOL yeah I know. But I assure you: none of these are science-based, generalizable, or come with any guarantees regarding your Hinge reply rate.)

Here are ten things I really love doing. If you enjoy any of them, you’ve got a place to start getting good at flirting.

1. If you enjoy reading about dating

You’re in the right place! If you’re curious about how people think, act, and interact with each other, you’re going to be curious about how they date. Well, ask them!

Ask couples you know how they first met and how they flirted; people love talking about this. Ask friends about their flirting misadventures, missed signals, and awkward situations. Ask for advice and also give advice if you’re asked. The goal of it all is to test and improve your intuition about how flirting happens in real life. This is how I’ve learned almost everything you read on these pages.

Just make sure you’re learning from real life, not from Reddit.

2. If you enjoy looking at hot people

Every hot person is a work of art. You can enjoy it knowing nothing at all, but you can enjoy it much more by cultivating your appreciation.

What is it about them that makes them hot? Is it the way he leans or the way she tosses her hair? The shape of his arms or the cut of her outfit? Are they beautiful in rest or in motion, in a self-unaware way or exactly because they know how hot they are? Notice the details and how they all come together. Classes in photography, fashion, or figure drawing can level you up rapidly here.

A beautiful person’s beauty is not an accident, it’s an expression of who they are. Recognizing this expression is the opposite of objectification, it’s seeing them from their own subjective point of view. Complimenting people on what truly makes them beautiful and unique is a flirting superpower. You can start practicing with your friends. Single or married, men or women — no one hates getting a great compliment.

3. If you enjoy improv and/or extreme sports

Flirting can get awkward, scary, and uncomfortable. Sounds like fun.

The best thing about improv is that you can practice it with people who have absolutely no idea it’s happening. Most people most of the time are playing out some scene with tropes and roles and status relationships. You can just “yes, and” and join it. They won’t stop you.

You can practice inhabiting the roles others cast you into or subverting them, creating awkwardness and returning to grace, reveling in conflict or resolving it. Flirting can never be 100% comfortable, but you can get more comfortable with discomfort through practice.

4. If you’re very online

The internet is full of bots and noise, but also men and women authentically expressing themselves. What do you love about the opposite sex’s posting? What confuses you? There are worse ways to learn about people than through their tweets or stories.

Social media is also a great space to practice banter and improv at low stakes. Good reply game is good improv game is good flirting game. Let Visa teach you.

5. If you’re embodied

Someone told me once that 93% of communication is nonverbal, but I didn’t really listen because they stood too far away with tense posture and skittish eye contact.

Flirting is about energy and emotion. These are expressed through our bodies. You can play with physical proximity, energy mirroring, taking up space, holding eye contact, and matching or shifting energy levels. Body language is for dialogue, you learn both to express yourself and to read what other bodies are telling you.

Dance, theater, even martial arts are all practices that make you body-aware in a way that translates to flirting. If you’re not in the habit, the mere act of paying attention to bodies yields good returns.

6. If you enjoyed the authentic wanting exercise

I’ve done a dozen follow-ups on the exercise in the last couple of weeks (it’s part of the reason why this post is late, sorry!) A lot of the guys expressed hesitation around approaching or asking out women in a way that’s related to the struggle of articulating what you seek. The goal of the exercise was to make your desires explicit enough to act upon. I often found myself asking: “what about a girl makes it more likely you’ll have a positive conversation?” or “what reaction to your initial approach would reassure you that she’s worth pursuing?”

The goal of flirting should be to discover if you’re what each other is looking for, not to force some outcome regardless of compatibility. This is an ongoing process, from spotting initial signals of chemistry to discerning the important qualities you seek through conversation. Knowing what you’re looking for and how to spot it makes flirting more fruitful, and it’s much more attractive than half-heartedness.

7. If you love the little details

Flirting is about paying attention, and attention is a scarce currency. People in conversation often let their minds wander, usually to themselves, and fail to notice or remember the details. If you do, your interlocutor will be delighted.

Practice with acquaintances. Did their hair change recently? Their mood? Did they mention a trip coming up or something that bothered them last month? Notice and remember the small things, ask follow-ups, and demonstrate your awareness. There is no more reliable way to be liked because attention is impossible to fake. And friends aren’t just for practice: they should be a prime target for slow, playful, plausibly-deniable flirting. Paying careful attention (combined with an eye on your own authentic desires) is the key that can unlock the romantic potential of a social acquaintance.

This skill comes into play in one-off conversations as well. How often do you talk to someone at a party and realize they forgot your name, let alone some detail you mentioned ten minutes ago? You can pleasantly surprise people just by putting effort into remembering.

8. If you enjoy deep conversations

Why do these lists always have to have ten items? Is God to blame for giving Moses ten commandments in a listicle? Ten is a lot. It gets monotonous for the reader and exhausting for the writer. So for #8 I’m going to tag in two friends:

Ava for the motivation:

I think that conversation is more important to me than anything else. I think talking is fundamentally erotic, which is why friendships are fundamentally romantic. And the point of a good conversation is to actually get somewhere. I’ve dated people where we just couldn’t get anywhere when we talked. There wasn’t this sense of fluidity, of breaking through. We never ended up anywhere new—we just circled the same streets repeatedly.

Sasha for the deliberate practice:

Personally, I try to assume that I can make conversations much better and that everyone I speak to could be a friend I haven’t met yet, or, at least, someone who’d like to be seen and understood. […]

Eventually I realized that human connection is one of my favorite things, and thus I’ve tried really hard to override my prior instincts. And I think I’ve done a reasonably good job. I think I’ve gone from “terrible” to “at least better than average,” and my job depends on being able to induce conversational depth with reliability.

Here are some notes from the overriding process. Everything that I’m writing here, I’ve had to learn the hard way.

9. If you like to observe like a scientist

Why learn from your own mistakes when you can learn from everyone else’s?

People are flirting all the time. If you could imagine two people dating, you can assume an undercurrent of romantic play whenever these two people are talking regardless of context.

But a scientist doesn’t just observe passively, she tests hypotheses. Can you notice patterns? Can you tell what’s important and what’s superfluous? Can you predict what works and what fails?

My wife’s a scientist and I’m a dating nerd, so when we spot a first-date couple next to us at the restaurant we both go silent to indulge in eavesdropping. Then we make our predictions on how the evening would play out for our neighbors. I’m usually the more optimistic, though not necessarily the more accurate one.

10. If you enjoy seeing people smile

This is really a combination of all the above, and the one that’s my personal favorite.

Credit to my wife, lemon markets connoiseur.

I banter ALL the time. I’ll point out funny things to a stranger at the grocery store. I’ll ask someone about a painting they seem entranced by at the museum. I’ll have conversations made solely of facial expressions with a baby in a stroller or the person across the subway aisle. If I can’t tweet it, I’ll tell the joke I just thought of to the first person next to me.

The most important requirement for flirting is the confidence that other people enjoy from interacting with you. You can’t fake this confidence. You can only build it by repeatedly observing other people’s enjoyment. And to observe this you need to repeatedly initiate positive interactions — an observation, a joke, a good question, even just a smile. Every time you get a smile back, you have leveled up your flirting game.

And really — it’s a level up in being a good and happy human being. Flirting isn’t a quarantined activity that happens in Tinder DMs and speed dating events. It happens everywhere (and if it isn’t, it should). It’s about fully expressing who you are and fully observing the other person. If there’s anything at all you enjoy about yourself and other people, you have a way to start gittin’ gud.