The Right and Wrong Ways to Flirt

Mark Manson
10 min readJul 15, 2024

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I n my previous article about Vulnerability in Relationships, I bashed using teasing/banter as a basis for demonstrating sexual interest. I referred to it as “a horrible mindset” and implied it was dishonest.

As usual, whenever I turn my nose up to this type of flirting someone always chimes in and says, “Aw, come on Mark, it’s harmless flirting. Why are you being so hard on it?” Some people even get upset, saying they “love” the verbal sparring that comes with this type of sexual interaction. They even get angry sometimes, like I just pissed on their dog or something.

But the reason I’m hard on derogatory flirting is because it’s a shitty way to instigate a sexual relationship. Fact.

Some people love the teasing and the innuendo and the “hard to get” stuff and the verbal sparring and the never-ending competition for dominance. These are usually the same people that are complaining that they can’t find a high quality man/woman and will bore you with calamitous break-up story after calamitous break-up story at the drop of a hat. Cry me a river.

Derogatory flirting sucks because it muddies the waters of intention and emotion, possibly the two most crucial components of a healthy sexual relationship (both short-term and long-term).

In derogatory flirting, you’re never quite sure of what the other one is feeling or meaning, and often you lose track what you feel or mean yourself. It’s designed that way. It distorts sexual interest, undermines consent, needles the other person into being insecure around you, and not to mention is absolutely exhausting to keep up.

Pretending you like her less than you do so that she’ll like you more than she says she does so you can then like her more than you say you do so she feels comfortable liking you back more than she says she does — I’m exhausted just writing about it.

But it also tees you up for future headaches. A number of people asked in regards to the previous article, “What if she’s manipulative but you just don’t find out until much later?”

That’s the problem. With derogatory flirting you don’t really see what the other person is made of until way down the road, often after it’s too late to get away without getting your face scratched. You could be going to bed with the most psychologically fucked person and have no idea. And for those of you just looking for a good time, this form of flirting is what creates that gnawing sense of having to constantly convince or even trick someone into sleeping with you. It’s not fun.

When you attract through honesty and vulnerability, you find out who you’re dealing with early on: their values, their intentions, their comfort level with their own sexuality, their beliefs about men/women and sex. You can screen these manipulative people out within the first couple minutes. You can also judge basic sexual compatibility within a couple hours. You never have to feel like you’re coercing anyone into sleeping with you. Since you’ve already been so open about your beliefs and intentions, a simple, “Let’s go to my place,” doesn’t seem out of line or inappropriate at all. It seems like a reasonable question and a logical next step in the interaction.

1. Sexual Rejection Is Shameful

English-speaking culture is unique in that rejected displays of sexual intention are seen as shameful. I believe this is the root of our bizarre flirting behaviors. A failed sexual pass at someone is grounds to be shamed and humiliated by our peers and society at large. This has been inculcated in us from a very early age.

(Note: By English-speaking cultures, I mean former English colonies and to a lesser extent Scandanavian countries.)

It’s important to understand the difference between shame and embarrassment or shame and guilt. Embarrassment is a temporary negative state due to an external situation. Guilt is the judgment of an action or external situation as bad or wrong.

But shame is an actual judgment of character. If you feel guilty about doing something, it’s the action that is deemed wrong or incorrect, not you. But if you’re shamed about doing something, it’s you that is deemed wrong or incorrect.

In our culture, we socially reinforce shame in each other for our failed sexual intentions. You see it in movies and TV shows, where the bumbling idiot with the girl is always the loser character, where the sexually expressive character is almost always the bad guy. You see it in high school and colleges where kids make fun of each other for their unrequited sexual intentions. Many families in our culture refuse to openly talk about sex to their children. Kids are discouraged to “experiment” when they’re young. Nudity is something to be ashamed of and hidden. Public displays of affection are ridiculed and people are told to “get a room!” so others don’t have to be exposed to their sexual interest in one another.

There’s just a general discomfort with sexual intentions that you do not find as prevalent in other parts of the world.

Sure, in other cultures, there’s some embarrassment and discomfort around some of these things, but their societies don’t actively shame people the way we do. Ask an Italian guy the last time he felt ashamed of telling a woman she was beautiful. Chances are he’ll look at you like you just crapped on his lawn.

The paranoia and fear, particularly in American culture, doesn’t help either. Girls cockblock each other out of some deranged honor code, as if every guy in every bar is America’s next serial rapist. Women are slut-shamed by both men and other women. Men are ridiculed for their lack of sexual conquests and then ridiculed even more for trying.

There’s shame everywhere. It’s a sickness. It causes epidemics of emotional/sexual dysfunction. And it inspires weird and inefficient strategies of displaying affection. There’s a reason dating advice is a nine-figure industry in the English-speaking world and not elsewhere.

2. Showing Affection Through Implication or Exaggeration

Since people in the English-speaking world are shamed into not showing affection or sexual interest overtly, we learn to do it covertly. We imply our interest and our feelings instead of expressing them openly. We’re taught that dating is a series of “signals” transmitted to one another in innocuous, mundane ways such as playing with one’s hair or “accidentally” brushing up against their leg or conveniently mentioning that one will be hanging out at the skating rink at 7:30 or whatever.

Humor accomplishes this well too. If you joke about liking the person, then you can display your true feelings without anyone being able to shame you for them. After all, it was just a joke, right? This then forces the other person to decipher what you actually mean or if you actually feel a certain way. So they might joke back to see what your reaction is.

Another more subtle form of implication is through exaggeration. Everything is “The best thing ever!” Even minor, annoying acquaintances are “best friends,” and mildly exciting occurrences are described as “awesome” or “totally insane.” These expressions get cheapened in our culture because it’s seen as inappropriate to express these emotions in a situation unless there’s been some sort of monumental occurrence. Therefore people pretend that everything is a monumental occurrence.

3. Affection Through Teasing and Insults

In the process of implying affection through other actions and words, it seems we agreed as a society to perceive teasing and insults as a socially acceptable form of affection and attention. This is most common in the UK, but exists everywhere in the English-speaking world. You bond with your friends by trashing them and embarrassing them. You flirt with girls by insulting them. It’s like a playground: boys are smelly, girls are icky.

When everybody decides that insulting someone in a humorous way is an indirect way to show affection, then it becomes the new norm. Guys make fun of each other. Girls challenge guys and are “sassy” when they actually like them. Men tease women and attempt to make them insecure and vice-versa. All of these behaviors aren’t just avoiding the actual emotions and intentions, but they become the socially acceptable way of demonstrating sexual interest.

Aww, look. They’re flirting.

A society that agrees that sexual interest should be demonstrated through dehumanizing and insulting another person is a screwed up society.

The problem here is two-fold. First, one is never 100% sure of other’s intentions, again leading to that murky area which leads to poor relationship choices. The second problem is that while we may consciously know someone is joking, our unconscious still internalizes it. For instance, if your friends always teased you by calling you “Shorty” growing up, even though they did it out of affection, it’s likely you internalized it and ended up insecure about your height.

While this may be good-natured ribbing, this derogatory flirting reinforces the already-dominant precedents of shame between men and women. If a girl blows you off and doesn’t sleep with you, not only do you face the shame of the rejection, but she spent half the night joking about your car and acted unimpressed by your job. This is the new norm.

The two best-selling dating advice books for men and women are The Rules (for women) and The Game (for men). In The Rules, women are advised to pretend they don’t like men that they’re actually interested in. They’re told to make him call her multiple times and to pretend to be unimpressed with him at all times. In The Game, men are advised to “neg” women into being insecure about themselves, usually about their appearance.

This is honestly what we’re taught in our culture. Like somebody? Then treat them like shit!

4. Overcompensation

The social stigma surrounding sexual rejection, the poor expression of emotion, the derogatory flirting — these things give sex a weight in our culture that you don’t find in many parts of the world. In the English-speaking world sex is a really big deal. In most other cultures, sex is an enjoyable side-effect of an otherwise normal existence. In the English-speaking world, sex is something to be worked for, fought for, and achieved. It’s talked about ad nauseam, and dominates our pop culture.

Because it’s taboo and requires so much social risk, people lash out and overcompensate. The English-speaking world has the highest levels of casual sex and one-night stands in the world. We also have some of the highest rates of alcohol consumption and binge drinking. The habit of getting really, really drunk and then finding someone to fuck is a cornerstone of our party culture (see: any movie about college) and few others.

You see this in pop culture: entire movies and TV shows built entirely around sex and the obsessions associated with it. Sure, sex sells the world over, but rarely do I see it glorified/stigmatized as much as I do in English-speaking culture. Sex is a large part of machismo culture for Latin men, but there’s no social shame for being rejected by the women and there’s no confusion about their emotions. Sex appeal is glorified in women in Eastern Europe, but you don’t see the slut shaming that goes on in the West. Prostitution is accepted as a normal part of life throughout much of Asia and men and women are not judged for participating in it.

To put it bluntly, most English-speakers are still on that same playground, calling boys smelly and girls icky, while sneaking behind a tree to kiss each other, still hoping nobody else finds out. We’re stuck in place, and largely because our society shames us for going any further than that.

Perspective

Now, before I get 500 emails telling me that I’m a reverse-bigoted asshole and that I generalize and that I don’t know anything and blah, blah, blah, let me pull this all together and throw a big floppy bow on top.

First off, teasing and some natural jibing between friends or two people who trust each other, there’s nothing wrong with it. It can be good, honest fun. The problem is when it becomes a basis of showing affection and appreciation to one another.

I recognize that no culture is perfect and other regions have problems that are just as apparent as ours. Let me take a step back and explain my little theory.

Historically, to thrive, all societies needed to figure out a way to enforce cultural cohesion and create social order. As Freud pointed out decades ago, historically, for a civilization to thrive, it had to have a way to cull and organize its people’s sexual impulses into a neat system. A civilization can do this in two ways: through formal institutions and laws, as well as through cultural norms and societal beliefs. Different cultures developed different cultural norms to enforce this social order.

Latin cultures have an intense fixation on romance, jealousy and possessiveness (it’s no coincidence that they have more infidelity than anywhere else). Islamic cultures do it through pure fear and retribution. Hindu culture does it by arranging marriages. Japanese culture does it through codes of honor and integrity.

And the English-speaking cultures do it through shame.

There is no “good” solution in any of these. All of them are repressive in their own way. Ours is repressive in that it inhibits open communication. It’s no surprise that the English-speaking countries have the highest divorce rates in the world (and it’s not even that close).

I suppose you could have the argument that our way is better/worse than the ways other cultures do it. But that’s a discussion for another day.

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Mark Manson

Author of #1 NYTimes Bestseller ‘The Subtle Art of Not Giving a Fuck’. OG Blogger. Psychology Nerd. I enjoy cats and whiskey. But not at the same time.