As more and more people get vaccinated against COVID, we’re all starting to step back into the world again. Just as importantly, people are ready to try to jumpstart their love lives again after a long, frustrating and lonely year of enforced solitude. And while there’s going to be an adjustment period as we all try to come back from having gone fully feral, one thing that hasn’t changed is the need for social skills. And while “hey, Pfizer, Moderna or J&J” may work for an opening line, a lot of people fumble at what comes next.
We may all be desperate for human contact, but understanding how to connect with people is still vital. And if you’re looking to break out of a pandemic-induced dry spell, then you need to understand how to flirt.
Flirting is one of the most important — and paradoxically, one of the most misunderstood — skills when it comes to dating. A lot of men assume that flirting is an incredibly specific process; you have to act and speak a certain way, demonstrate your value or worth and show that you’re the best possible choice out of everyone else at the bar. By doing so, you generate powerful attraction — even in the most obstinate of women — and get her number or a shared Uber back to your place.
Except… that’s not how flirting works. That’s not how flirting works at all.
Flirting isn’t about generating attraction and interest where there isn’t any; in fact, if someone isn’t interested in you, trying to flirt is likely going to make them roll their eyes so hard that they can see their own brain. Flirting, at its most basic, is about signaling your interest, gauging potential attraction and — most importantly — engaging someone on an emotional level.
In fact, the emotional engagement is the most important part of flirting. It’s what captures somebody’s attention, what draws them to you and what encourages them to want to spend more time with you. Flirting is about having fun, not trying to get laid. You are showing your interest in someone in a fun and engaging way, while inviting them to join you in that fun. In a very real way, flirting is the art of giving people permission to do something that they already want to do: enjoy themselves with someone who’s warm and charming. People often enjoy flirting for its own sake — not because they want to hook up but because they enjoy how it feels. Flirting can be a game. Done properly, flirting is about the fun you have together, not what the end results may or may not be.
Once you understand this fundamental aspect of flirting, the rest comes much more easily.
So let’s clear up some misunderstandings and talk about how to get better at flirting.
Flirt As You Are
The first and possibly most important part of flirting is to understand that flirting is personal and specific to who you are as an individual. Your flirting style should match who you are as a person.
The mistake a lot of people make, especially when they’re starting out, is that they try to model themselves and their flirting style after someone else. Sometimes this means trying to model themselves after someone they think is the epitome of what women want — Tom Ellis in Lucifer, Robert Downey Jr. as Tony Stark. Other times it means trying to follow somebody else’s flirting technique as though it were a #ForbiddenLifeHack — negging or “cocky-funny“.
The problem is that this isn’t who they are.
Ok, well, that and negging or cocky-funny is more likely to earn you a visit from the Slap Fairy than to get you numbers.
But even under ideal circumstances, trying to be someone else doesn’t work for you. At best, you come off as a try-hard; you may be earnest, but it’s not appealing in the slightest. At worst, you come off as completely inauthentic and fake. And to make matters worse, if you aren’t authentically someone who’s arrogant-but-funny-enough-to-pull-it-off, then you certainly aren’t going to be well-calibrated enough to flirt like the people you’re modeling yourself after… which just serves as another invitation for a return visit from the Slap Fairy.
The key to keep in mind is that there is no one way to flirt. Flirting styles tend to be as unique as the people who use them. Here are a few different examples of flirting and flirting styles:
For example, there’s Don Draper and Joan Holloway
Craig Ferguson is famous for flirting with the women he interviews.
Elise Sellas and David Norris have a couple of excellent moments in The Adjustment Bureau
And of course, you can’t talk about flirting and not include that scene from Out of Sight.
Nor can you bring up flirting and not mention Gomez and Morticia Addams…
Each of these demonstrates different styles of flirting that are as unique as the people or characters involved. Don Draper is low-key and smooth, while Craig Ferguson is all about the teasing and innuendo. Elise and David have a very antagonistic, banter-y style of flirting, while Karen Sisco and Jack Foley play games and dance around the obvious without actually saying it. And of course, Gomez and Morticia are all about the comments and passion. Each style aligns with their personalities, which makes their flirting sincere, authentic and natural.
Trying to flirt like, say, Don Draper when you’re not a smooth operator is going to work against you. But you don’t need to be smooth and polished. You can be stammer-y and awkward and still flirt successfully:
It’s about making sure your style is in alignment with you as a person. The more you understand yourself and — importantly, what works for you — the easier it is to flirt effectively.
But how do you figure out what works for you? Glad you asked, convenient rhetorical device…
Flirting Isn’t About Sex, It’s About Emotion
The mark of someone who’s good at flirting isn’t how many women they bring home or how many numbers they get on any given night, it’s how many people want to talk to them. Someone who’s good at flirting is simply fun to talk to. The fact that he can keep people entertained is the reason why women are going to want to talk to him instead of someone else. But the key is to flirting is that it’s about conversation. The most successful flirts know how to keep people engaged and interested without coming off as “holding court” or talking at people. Flirting, after all is a participatory activity. There’s a vast difference between flirting with someone and practicing your tight five for the open mic night at the Comedy Cellar.
This is why, while flirting may be serious business, it’s rarely serious. It’s about generating and eliciting positive emotions: laughter, smiles and pleasant surprises. Part of Craig Ferguson’s skill at flirting comes from the occasional unexpected and absurd responses he gives to questions. Because they’re so surprising, they get a laugh almost immediately. That, in turn, helps make him more fun to talk to.
This is important because love and attraction aren’t just emotional, they’re chemical. Much of what we experience as “love” is the generation and uptake of oxytocin. Oxytocin increases feelings of trust and relaxation, encourages social bonding and makes you feel amazing. We like how that feels, so we prioritize our relationships with the people who are capable of bringing that out in us — what’s known as the Reward Theory of Attraction. And two of the ways we can cause the generation of oxytocin in others is through laughter and good conversation.
If you go back to the clips I shared, you’ll notice just how much everyone is laughing and smiling. Even when Elise and David are ribbing each other, they’re both clearly having a good time. They’re enjoying the interaction; it’s fun for them, rather than needling at someone they dislike. Flirting, even antagonistic flirting, is a game. It’s about having fun; you may be teasing someone, but you’re pointedly teasing them about things that aren’t important or significant to them, things that they can easily laugh at.
Understanding that the point of flirting is that it’s fun is what makes it possible to flirt in many different ways. You can flirt — as Karen and Jack do — by doing mini role-plays, pretending to be other people or crafting shared scenarios. Don and Joan — friends, coworkers and people who know and respect one another — are sharing a moment together, laughing at themselves, at each other and complimenting each other even in refusal. You can flirt in text by sending GIFs back and forth. You can tell stories and share secrets or even just ask questions.
In fact, part of what makes somebody more successful at flirting is that they flirt because it amuses them. That sense of “it’s all good fun” is contagious, and encourages others to play along; they know it can be as serious or not as they want it to be.
Just as importantly though…
Flirting is Persuasion
One of the ways to think about flirting — and to find your most effective flirting style — is to think of flirting as a way of encouraging someone to do what they already want to do.
As an example: think of how you would persuade someone to get into a nice cold pond on a hot day. You can’t just pick them up and throw them in; you have to convince them to get in with you.
There are any number of ways that this could be accomplished. You could use obvious reverse psychology:
“Nah, you’re right. It’s probably too cold. We’d get hypothermia and then have to bundle up for warmth to survive. We’d better just stay up here and broil instead.”
Alternately, you could tempt them with how good it feels to be in the water; cool from the waist down, warm from the waist up. You can tease them about being afraid of the water, or even encourage them to go first because you want to know if the potential shrinkage is worth it.
The same philosophy — how do you encourage someone to do something they would enjoy or want to do — applies to flirting. This is, in fact, one of the reasons why playing games can be a great — and versatile — way to flirt. Whether you’re out together in person or talking via text or WhatsApp, you can use games in order to create the playful atmosphere that encourages opening up and being open to taking things in all sorts of interesting directions. Seemingly simple or even cheesy ice-breakers like “Two Truths and a Lie”, “Would You Rather” or playing “Confessions” where you each pick a topic and share a secret about it all offer opportunities for fun, teasing and also a little naughtiness.
You can even do mini role-plays or invent absurd scenarios together; I’ve flirted with someone by taking a misunderstanding from something I’d said and turning it into an imaginary scenario of making a movie together. As we went back and forth it quickly became a story about filming a high-budget “art” movie and how to resolve the tension between our artistic vision…
What’s great about using games to flirt is that it creates a safe space of sorts; it’s not you doing these things or discussing these things, it’s this theoretical situation. You create distance because it’s all in fun; it’s just a game, but one that allows you to feel safe enough to open up without feeling too vulnerable. And that makes it easier for the both of you to take ownership of what you really want to do.
But while we’re on the topic of safety…
Sexy Flirting Has To Feel Safe
…the topic, that is.
Just as nobody likes The Horny Guy during games of Truth or Dare, sexy flirting can be fun… but not when that’s the only thing that someone wants to talk about. Even folks who might appreciate a little ribaldry or like a sexual edge to their flirting are going to be turned off when their flirting partner seems to have only one thing in mind.
That’s not to say that you can’t bring up sex when you’re flirting or that your flirting can’t have a sexual edge. As with all forms of flirting, it’s about the emotions more than the topic.
Craig Ferguson, for example, is notorious for how sexual his flirting would get during his interviews. However, rather than feeling uncomfortable, it’s rather clear just how much the people he flirts with enjoy it. The reason why it seems so easy for Ferguson to take the topic in any number of risqué directions is simple: he makes it safe for the people he flirts with.
A lot of men who try to add a sexy or seductive edge to their flirting — or just go hardcore on the innuendo — is that they go overboard. They bring up sex too often or in increasingly un-fun or not-funny ways and it inevitably backfires on them. Instead of being a fun, spicy or occasionally lewd game, it just becomes creepy. They’re clearly not paying attention to the comfort or interest of the person they’re flirting with. They’ve made it all about what they want.
That’s why the first key to adding a little spice to your flirting is to keep it light at first. Mild innuendo or playfully and deliberately misunderstanding something allows you to bring up the topic in a way that also serves as a ping for interest in playing along. How does she respond? Does she pick up the ball and run with it? Then there’s a little more room to play — especially if she teases or plays right back.
On the other hand, if she seems flustered — and not in a good way — or ignores the topic, then you back off.
By that same token, you don’t lead with your dick. You don’t bring up the topic right away, especially with someone you don’t know well or don’t have that kind of relationship with yet. It’s better to ease into it in a way that feels natural. This is another area where games like “Would You Rather” excel; by the time sex or sexy topics come up, it feels like a natural extension of what you were already talking about.
Just as importantly, you need to help her feel safe — physically and emotionally. On the physical side, this means giving her room… literally. A common mistake that guys make is that they take the flirting sexual while they’re physically close. While this can be hot, when you’re flirting with someone you’ve only recently met or are still getting to know, this can make women feel trapped. Giving them space — leaning back, not cornering them or backing them into a wall and making sure they have plenty of room to get around you — goes a long way towards helping them feel safe, physically. Knowing that they can leave at any time without the risk of being grabbed is important.
On the emotional side, this means you want to be warm, friendly and non-judgemental. You want to make sure you have a sincere, warm smile, so she knows it’s all in fun. Being non-judgmental is also vital; nobody, no matter how attractive they find you, appreciates someone who is going to slam them for their experiences — or lack thereof. You need to embrace your inner Jack Harkness and welcome her as she is.
Regardless of how kinky or standard-issue she may be, whether she’s slept with fifty guys or no guys, it’s all good. The whole point of sex is that the two of you are collaborating to have a good time; nobody feels sexy when they’re being judged. If she has more experience than you then, hey, that just means she has that much more to bring to the table. Or the floor. Or the back seat. If she has less, then you’re in a position to show her the ropes… possibly with actual ropes.
But that’s not going to happen if she doesn’t feel safe enough to share; attraction doesn’t exist without feeling safe.
But even if the flirting is getting hot and heavy, it’s important that you don’t let that be the only thing. Changing the topic to non-sexual matters or deliberately breaking rapport with a light tease (not a neg) releases the pressure and keeps things interesting.
In fact, about that…
It’s All About Balance
One thing people often don’t realize about flirting is that flirting is all about balance. Most men don’t realize that flirting is an on/off thing. If all you do is joke or tease, then it quickly becomes tedious and you teach the person that you’re flirting with never to take you seriously… even when you’re trying to be vulnerable and real. Similarly, if you’re giving nothing but innuendo and “funny” misinterpretations, then you end up being boring at best and a perv at worst.
The same thing applies to compliments. Even if your compliments are well received at first, it doesn’t take long at all before you sound like you’re a suck-up, not a sexual Jedi. Everyone likes being told they look amazing or that they’re hilarious; too many compliments make even the hottest flirting turn into a try-hard kiss-ass fest that nobody enjoys.
You need to keep a balance between flirting and being serious (but fun). Alternating flirting and teasing with being genuine and sincere is a small thing that pays off in huge ways. It keeps people off balance in a good way, because they are never entirely sure what to expect. Interspersing those playful moments with points of vulnerability, or leavening serious moments with a well timed tease, innuendo or even an absurd response to a question keeps things interesting. It’s a roller-coaster in the best ways and — importantly — makes talking with you fun. You’re never so frivolous that you don’t have moments of insight or realness, but also not so serious that it feels like every conversation feels like deep dives into 19th century philosophers.
Backing off the flirting and being serious on occasion keeps the entire conversation more interesting. It also creates a vacuum of sorts, encouraging the people you’re flirting with to fill it themselves. Pulling back on the flirting means that the good feelings that came with the flirting are pulled back as well. They want those good feelings to return, and so they’ll often dial up the flirting on their end. This helps create a self-reinforcing cycle as both of you become more invested in the moment and each other.
The most important thing to remember though is very simple:
Confidence Is Key
In the before times, in the long-long ago, when I would watch folks trying to hook up at bars, I saw guys all make the same mistake over and over again: they never committed to the bit. I can’t count the number of men I saw who would attempt to flirt and then immediately back off or apologize for even trying.
Small wonder that they would consistently leave with their tails tucked between their legs.
Confidence is vital when it comes to flirting and building attraction; flirting simply isn’t fun if you can’t commit to it. If you can’t own your interest, then you can’t flirt. There’s no way around it. The “ha ha, just kidding… unless you were gonna do it” gambit is, quite frankly, limp. If you are interested in someone and want it to go somewhere, then you can’t flinch at the first hint that it’s not going perfectly. If you’re afraid to put your desire — including sexual desire — out there, then you aren’t going to be able to get anyone interested in flirting with you. Putting out a tentative feeler and then pulling it back immediately isn’t a good look on anyone. All it does is signal either a lack of confidence or a lack of social and emotional intelligence… and neither is attractive.
This doesn’t mean you have to be perfectly smooth or confident; it just means you have to own it, even if your knees shake and your voice quivers.
Confidence is what makes flirting work regardless of whether you’re as smooth as glass or rockier than five miles of bad road. Even the cheesiest or dorkiest attempts at flirting can be charming with the right attitude behind them.
But confidence is vital in the ways you flirt as well. You have to be willing to invite them to tease you back and to roll with it. Part of what makes the flirting in The Adjustment Bureau clips work so well is the constant use of “yes, and”; both David and Elise roll with and build on the things that they tease each other over instead of pushing back. This is important. It demonstrates that you’re perfectly willing to laugh at yourself and that this is all in fun.
(Just realize there’s a difference between inviting being teased and laughing at yourself and a constant stream of self-deprecating humor)
However, confidence is also important in how you handle things when it doesn’t go the way you hoped — whether you are getting the gentle swerve or turned down directly. In the Mad Men clip earlier, Joan is teasing Don and telling him “no”, repeatedly. And yet despite that, he takes it all in good humor. It’s no big deal to him; while things would be fun, he’s also just enjoying flirting with Joan. He’s willing to laugh when she nudges at him, smiles and laughs when she turns him down and gives as good as he gets. It doesn’t upset him because sometimes flirting is just for flirting’s sake.
Just as importantly though, showing that you can be turned down and take it with good grace is huge. It shows that you’re safe. It shows that you’re emotionally intelligent and confident. And that can turn things around. You may get another chance to flirt… or you may soon find others who want to flirt with you… and take it much further.