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The other day, someone I had just met just minutes earlier, decided to inflict a deeply personal question on me. It was intrusive, inappropriate and entirely unprompted. But the incident also got me thinking: Why do some people feel so comfortable crossing social boundaries by asking questions that are pretty much none of their business?

Now I realize that what’s considered inappropriate in one culture may be perfectly normal in another. But I’ve found that the people who tend to ask me these kinds of questions don’t generally come from cultures where such directness is the norm.

So what’s driving that impulse? Are these people genuinely oblivious to social boundaries, or are they deliberately trying to make others uncomfortable? Could it be a way of asserting dominance? A test of how much they can get away with? A sense of entitlement?

“Asking questions is how we create connections, learn more about each other, and create intimacy in relationships,” says Dr. Carolina Estevez, PsyD, a Psychologist at Soba, a treatment center in New Jersey. Most people, she explains, can discern which topics are appropriate to discuss with whom by getting a read on the relationship, setting, and social cues. Others genuinely struggle to read the room. But for some, she says, “[they] may treat invasive or deeply personal questions as a test of how much access the other person will give them.”

There can also be a more narcisstic element at play. “Some do it simply to satisfy their own curiosity without caring about the consequences,” Dr. Estevez explains.

Whatever the motivation happens to be, invasive questions tend to catch us off guard. And that, Estevez says, can make them particularly tricky to navigate. “Due to the unexpected nature of the question, and the fact that many people are raised and socialized to be cooperative and polite, sometimes answering feels like a better solution than refusing and being in an uncomfortable or awkward situation,” she says.

There’s something rather curious about that dynamic. Even though it’s someone else who had created the awkward situation, too often it is the person on the receiving end who somehow is left feeling responsible for resolving that discomfort.

In a way, invasive questions can be viewed as an invasion of privacy. Stephanie Lewis, a long-time therapist and VP of Clinical Operations of Epiphany Wellness, a network of addiction & mental health treatment centers, argues that invading someone’s privacy doesn’t always require hacking into their personal data. It can be done through subtler means: “like asking continually bolder and more invasive questions as a conversation progresses.”

This can also become a form of controlling behavior, particularly in public or group settings. As Lewis explains, the person being questioned is “forced to defend themself or reduce the tension by answering the question, even when they don’t want to.”

Of course, not everyone who asks an intrusive question has some sort of ulterior or nefarious motive. Most people are simply curious, socially clueless, and perhaps don’t consider certain subjects to be as private as we might. They often don’t even realize their question has crossed a line. If they did, perhaps they’d reconsider asking.

But it’s just as interesting—if not more—to understand why it is that we feel compelled to answer? Why does refusing to share something personal sometimes feel more uncomfortable than sharing it despite not wanting to?

Couldn’t we simply respond with: “Sorry, I’d prefer to keep that private” or “That’s a bit too personal for me to talk about right now.” Neither response is actually rude. And yet many of us hesitate to set those boundaries. Why? Is it because we’re afraid to appear unfriendly? Guarded? Difficult? Are we afraid that if we refuse to share they will view it as a rejection of their desire to connect?

Why do we worry that setting a boundary will cause discomfort? And, more crucially, why is it that we feel responsible for sparing someone the discomfort of being told they’ve asked an inappropriate question, even when they’re the one who put us in that predicament to start with?

Perhaps part of the problem is that we’ve been conditioned to prioritize other people’s feelings over our own. We’d rather betray our own privacy than create awkwardness for someone else.

But being asked a question doesn’t mean that we owe anyone an answer.

How many times have you answered a question you didn’t really want to answer? And how did you feel afterward?

No one is entitled to your story just because they’re curious enough to ask.

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Michael Douglas has just released a memoir, “One Helluva Ride.” He’s 82 years old now and seems willing to tell all. Or at least more than most movie stars of his stature would.

And he certainly has quite a lot to tell.

He started off his journey as the son of screen legend Kirk Douglas, then found his own footing as an Oscar-winning actor and producer. He married Catherine Zeta-Jones along the way (his second attempt at marriage). And had some kids. And, of course, he also gave us Gordon Gekko. Throughout his career he saw the entire machinery of celebrity transform.

There aren’t a lot of Hollywood stars like him left these days. And the younger generation of stars inhabits a very different publicity ecosystem. They are far more cautious, heavily media-trained and rather acutely aware that almost anything they say can be clipped, posted and over-analyzed online. Or worse.

That isn’t to say that old Hollywood types aren’t guarded—they are—and they know how to play the game. Douglas certainly does. But people like him came of age in a culture where stars could still say something candid, blunt or even mildly ill-advised without having to worry that this one stray comment would be stripped of context, go viral and destroy their career.

Years ago, I interviewed Douglas about a film he had at the Toronto International Film Festival. He was truly ‘old school.’ He made sure to know my name and outlet before I came in, greeting me warmly. And then, he offered me a drink or ‘anything else’ to make me comfortable during the very short time we had together.

Obviously they were merely polite gestures. I did not expect him to fix me a martini. Though I wish I had asked just to see his reaction. Instead, “No thank you,” I replied, “But that’s very nice of you to ask.”

“Well, I’m a very nice guy,” he responded.

I immediately pointed out that a nice guy wouldn’t say that.

Then things went a little sideways.

Interestingly, in many people’s minds Douglas has become almost synonymous with playing bad guys. In reality, however, he hasn’t played nearly as many as you might think. But you can be forgiven for thinking otherwise, given just how long Gordon Gekko’s iconic shadow has loomed over his career.

“Everybody likes to play the bad guy,” Douglas told me, “because it’s more fun to play.”

“You vicariously get to do things that other people would love to do. You get to be bad. And the realities we all attempt in life give the best impressions. Why are some ladies attracted to bad boys? Why do some guys like bad girls? There is an element of danger, there’s an element of unpredictability and it’s fun to play.”

Douglas certainly doesn’t shy away from Gekko. “Gordon Gekko was one of the best parts I’ve ever had,” he declared. “It’s certainly one of the top three.”

And, of course, it won him an Oscar, didn’t it?

“And that became kind of an archetype, Gekko and all of that whole culture,” Douglas told me. “So anytime you go near that area, it’s natural that it should be brought up, but it’s not that I’ve done it so many times. It’s just that I’ve done it effectively.”

He has a point. Some performances become so culturally indelible that they begin to swallow the actor who created them. Gekko became bigger than Wall Street. The slicked-back hair, the suspenders, the “greed is good” philosophy—all of it became shorthand for a particular kind of American ambition and excess.

Of course, nobody likes to think of themselves as the “bad guy” while playing one. Or, for that matter, while doing anything else.

“No, you don’t think of yourself, you just think about what your mission is,” he responds, “You just assume that the screenplay is good and [as] you’re playing your role it kind of clarifies itself.”

That idea of moral ambiguity runs through much of Douglas’s career. He likes thoughtful films.

“It’s like a restaurant,” he explains. “You’re hungry. There are fast food [joints]...you can get two hours of entertainment and walk out of that theater after two hours and you go, ‘Well, that was fun.’ And you get on with your life. Or, if you’re fortunate enough, you could have walked out and the movie stays with you or the ideas and thoughts stay with you.”

That, he says, is what he has generally looked for in the characters he chooses.

“So, yeah, I like food for thought, given the cost of making movies, rather than the fast food.”

Douglas has played so many characters that are difficult to categorize in simple terms. Ambitious and charismatic, damaged and selfish, powerful yet vulnerable. Even when they behave badly, there’s more to them. Something that we can recognize in ourselves, perhaps.

Greed, of course, seems to be at the crux of people like Gekko—not to mention plenty of real human beings around the world. So is it that wealth corrupts people? Or is it that corrupted people are simply more willing to pursue wealth because they're prepared to do whatever it takes to get it?

What comes first: the chicken or the egg?

“Well, if greed is your main motivation and purpose for existence,” responds Douglas, “if that is what drives you, just the accumulation of money, then you’ll attempt to do it—however you can—to make more of it. So it’s the Midas touch.”

All of us have a dark side or selfish cravings, but often we tuck them away in an undusted corner, fighting against those instincts. Sometimes, deep down, we want to give in.

“Yes, I believe we all have evil in us,” Douglas tells me.

“Do you struggle to do the right thing?” Douglas asks. “In most cases, people try to. In other cases, they don’t. And I like to kind of [take] those characters that audiences love to hate and then somehow seduce the audience by the end of the movie. They’re almost over on your side.”

People aren’t just all good or bad, and that complexity is what makes characters interesting. Douglas isn’t a nice guy or a bad guy either. He’s a complicated human being, like the rest of us. His willingness to let some of those flaws show is what makes his memoir more interesting than some carefully polished version of his life that reads like a press release.

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There is something about humans that tends to orient us toward rooting for the underdog. Somehow, the person with the least power becomes the person we assume is more right. The fewer advantages someone has, the more virtuous they must be. The less power they possess, the more likely we are to view them as a victim

We might suspect this isn’t necessarily true, but on some level, most of us can’t help but root for the underdog. Years of movies and novels have conditioned us to see the world this way.

After all, who is going to write a story about someone who has everything going for them? Where’s the conflict in that? Where’s the drama?

Just imagine: The scene opens and we fade into a luxury living room with a warm and loving families playing board-games while eating takeout. No one argues. Everyone’s kind to each other. And they have lots of dogs around, which is the most important part. Credits roll.

If we see someone making all the right decisions, we think: Alright, good for them. And …

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Hunter Biden has been doing the podcast circuit with all the best people, like Nick Fuentes, Candace Owens, and Tucker Carlson. At first, I gave him the benefit of the doubt. When he went on Candace’s podcast, I thought, maybe he wants to reach all sorts of audiences to include them in a conversation about addiction. Then he talked to Nick Fuentes, and I thought maybe he’s trying to reach people who would never listen to him otherwise. And then most recently he went on Tucker’s show and that’s when I knew he’s just full of #$#$#.

But here’s why. Or at least one of the reasons why. I have no desire to do a deep dive into the entirety of his conversation with Tucker.

Biden went on about how much he loved Candace and how she’s such a wonderful person. He pointed out that they had differences of opinion, but this didn’t take away from how good a person she is. He was practically gushing.

Well, I beg to differ.

This is a woman who has spent years spreading demonstrably false and deeply malici…

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I tend to look at my own over-reliance on technology as a failing. A crutch. An addiction.

Our devices, in many ways, make our lives easier. They empower our curiosity, help connect us, and allow us to build new things.

But they also make it more difficult to pay attention, be present, or tolerate boredom. We use our devices to escape all sorts of discomfort, including social awkwardness, instead of powering through.

But as my guest, , an attention activist, argues—compulsive tech use isn’t necessarily a failure of discipline. In fact, it may point to an underlying need.

Instead of being slaves to technology, Jay believes that we should foster a more intentional relationship with technology and that starts by better understanding why we are reaching for our devices in the first place. What are we missing? Play? Connection? Inspiration?

He argues that technology reflects the values and incentives we build into it—and that we can design technology to support connection, compassion, creativit…

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In 1974, a performance artist in Naples, Italy stood passively for six hours while the ‘audience’ could use a range of 72 objects on her in whichever way they wished. She would not resist, for these six hours she’d surrender her own agency to the crowd and take responsibility for anything that happened. She’d remain completely passive.

She left written instructions: “There are 72 objects on the table that one can use on me as desired.” And, “I am the object.”

The artist was Marina Abramović and the piece was called Rhythm 0.

But perhaps it is best viewed through the lens of a social experiment of sorts—decades before the MrBeast era.

Of the objects provided there was quite a range.

Some were benign: A rose. Honey. Bread. Apple. Comb. Lipstick. Cotton. Flowers. Mirror. Brush. Wine. Book. Perfume. Polaroid camera.

Others, less so. Whip. Pocket knife. Chains. Nails. Kitchen knife. Saw. Hammer. Axe. Razor blades. And finally, a gun and bullet.

At first, the audience was hesitant, gentle and playful. They offered her flowers, or wrote and drew on her body. They turned her position.

But eventually things escalated. Once participants realized that there would truly be no consequences for what they’d do to her, they became more aggressive. They cut her clothes until she was half-naked, violated her bodily boundaries, sliced her skin until she bled, and pointed a loaded gun at her head.

The person holding the gun tried to manipulate her fingers towards the trigger to see if she’d resist. It was aimed at her.

It was at that point that some spectators intervened and took the gun away.

Once the six hours passed, Abramović began to walk toward the crowd. Unable to face her, those who had been willing to touch, cut, strip, and injure her had literally fled the gallery.

She was naked, bleeding, and crying.

No longer just an object but a human, they couldn’t face her.

It was a heartbreaking lesson about human nature. She said: “The experience I learned was that…if you leave decision to the public, you can be killed.”

When you remove consequences, there will be people who will do the worst.

“I really feel I was a mirror to the public, so however the public felt, it was projected on me.”

But there’s another lesson here—perhaps a more significant one. It is about what happens when others remain silent.

Most of the people who were there didn’t necessarily participate in the acts of cruelty. Most of them simply watched in silence.

It was only when the situation escalated significantly that some people ended up intervening. But it was limited.

After someone cut her neck, another spectator put on band-aid over the wound. When the gun was aimed at Abramović, several spectators physically confronted the person and took the gun away.

That intervention possibly saved her life.

But the silent played a role. As some became increasingly aggressive, their silence allowed them to continue. It was, in a way, perceived as permission. And a lack of social consequences.

Once people began to act, they were able to prevent further harm to her.

But the silence, one could argue, was part of the abuse. And why were they silent? Was it a desire to fit into the group? Conformity? Vicarious abuse and morbid curiosity? Fear of judgement? Not feeling responsible for the actions of others? A belief that someone else would intervene if things were really that bad? Support?

We don’t know.

But these are the same forces that can keep people silent when they witness all kinds of wrongdoing. We don't necessarily need to approve of something to allow it to continue as long as enough people stand there and do nothing.

To me, it is a more interesting question than why people hurt her in the first place. Some people will always have it in them to hurt other human beings when presented with the opportunity. That’s the unsettling reality of human nature. But whether they are able to do so and how far they can go depends enormously on the environments around them.

When people are silent. When they don’t intervene in the damaging actions of others. That’s when such wickedness is able to thrive. When everyone watches a disturbing thing happen, it gives it permission to continue. Silence isn’t neutral because of what it allows to happen.

But when someone steps in, it often encourages others to do the same as well. They see that someone else sees that something is wrong and is willing to do something about it.

Just as silence is contagious, so can courage be.

In my book, No Apologies: How to Find and Free Your Voice in the Age of Outrage, I deal with a lot of the same themes about the pressure to conform, our fear of social consequences, and the tendencies we have to see what everyone else is doing before deciding to speak up. It also deals with the tragic consequences of remaining silent in certain situation.

Often, the opinions we believe to be unpopular are shared by a lot more people than we think. And, sometimes, the truly unpopular opinions are the morally correct ones.

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There’s something we don’t talk about very much. It happens to all of us, but most of us would like to avoid it.

I’m talking about aging.

We’re living longer. That’s a good thing, right? And yet, the caregiver pool is shrinking or feeling burnt out and overwhelmed. And many people prefer to avoid talking about it.

That’s why I spoke with Chia-Lin Simmons, CEO of LogicMark, one of the leaders in medical alert, health communication, and personal safety technology. Simmons is a tech veteran who has worked at Google, Audible (during its sale to Amazon), Samsung, and with various startups in Silicon Valley.

When she joined LogicMark in 2021, the company was still rooted in the classic “I’ve fallen and I can’t get up” medical-alert model. She wanted to rebuild it for the new world we find ourselves in. One of connected homes, longitudinal data, AI, and people who still want to retain the human aspects.

But what does that actually look like?

We discuss the future of aging and the role that tech…

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There’s a sci-fi movie I’ve been meaning to see for a while and this weekend I finally ended up watching it. I’ll avoid naming it outright because I don’t want to risk spoiling it for anyone who hasn’t seen it. But, suffice it to say, I had really enjoyed it.

During one pivotal scene, tears began to form in my eyes because a character I had grown deeply attached to looked like it might meet its demise. I gasped at the screen: “no.” In my mind I was already mourning. It seemed inevitable. In a ‘serious’ work, someone has to die.

I couldn’t even fathom a completely happy ending because I’ve grown so accustomed to things taking a darker turn, especially in movies.

That’s the traditional formula. You get the audience to care about a character—or several of them—but in the end you must sacrifice someone for the story to have emotional weight. That’s how compelling storytelling hits you in the ‘feels,’ or so it goes.

This was unexpected.

A genuine happy ending. No one we’ve grown to care about …

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Many people imagine that journalism has fallen from some golden age of objectivity into today’s landscape of partisan media outlets, influencer commentators, and algorithmic outrage.

But that’s not quite its origin story.

As I wrote in my Skeptic column, journalism did not begin as a neutral profession dedicated to informing the public. It began as a political tool.

The earliest newspapers were openly partisan enterprises. Publishers often had explicit ideological allegiances and, in many cases, direct ties to political parties. Their purpose wasn’t to relay facts (or even turn a profit). It was to persuade, mobilize, and shape public opinion. Journalists at the time were active participants in political battles, not detached observers. This wasn’t a secret. It was the standard.

Then, the focus turned to a more commercial endeavor, and thus the late nineteenth century became the age of yellow journalism. Newspapers began to compete aggressively for readers through scandal, emotion, exag…

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My memory used to be good. Genuinely good. As a kid I could replay whole animated films in my head, frame by frame. I memorized texts without trying. And then, somewhere along the way, that ability just left. I don’t fully know why. Perhaps you can relate.

But, suffice it to say, memory has been on my mind.

That’s why I was looking forward to my conversation with Dr. Anthony Metivier, who has spent years building memory techniques and teaching them to other people—partly, it turns out, because his own memory is bad too. That surprised me. He wasn’t a guy with some rare natural gift to remember things. He struggled with his own memory.

Which, should make us hopeful. Because memory, as it turns out, can be improved. Significantly. It’s a matter of skill, not just innate talent.

We also discussed deeper questions about technology’s impacts on our cognitive abilities, the internet as humanity’s external memory, what happens when it vanishes, and the balance between preserving the past and l…

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There was some sort of spat over the weekend between Dar Sleeper, vice president of product and design at 1X, and WIRED. Sleeper had provided WIRED with an exclusive on 1X’s $20,000 humanoid robot and he felt “betrayed” by the magazine’s coverage, alleging that WIRED turned it into a story about “sexualizing robotics.”

I read the story. It expressed some skepticism, especially surrounding privacy issues. In certain situations, 1X allows a human ‘specialist’ to take over the robot remotely. The reporter also argued that one of 1X’s advertising had displayed sexual undertones. Perhaps that was entirely unintentional by 1X and the reporter read into it too much. Perhaps not. Perception can be subjective.

But setting all of this aside, I think the broader public reaction to humanoid robots and having them in their own homes raises some genuinely interesting questions.

Some people compare owning a humanoid robot to slavery. I don't think that analogy holds. A robot is no more a slave than a…

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I've been scheming about new perks for my paid subscribers, and the verdict is in: people want to talk to each other about interesting things. Who knew.

So here’s the pitch: build a community, have great conversations, and throw a bunch of random minds into a room (virtual, for now) and see what happens.

Assuming there’s sufficient enthusiasm, I’m looking at launching The Random Minds Roundtable, a monthly (to start with) discussion series where we'll tackle the kind of topics I cover here—except this time you don’t just read silently.

First session is open to everyone who applies. After that, most (but not all) sessions will be prioritized for paid subscribers and invited guests.

Spots will be limited, and I’ll be curating each group to keep the conversation and mix interesting—so if you’d like to be considered, please apply via this form. Your answers will also help me gauge interest and shape the series.

You can join via video or audio (if you’re feeling shy, or want to stay anonymous).

Sign up!

The big idea: connect with other curious people, swap ideas, get talked out of your own opinions a little, and dig into the stuff that actually shapes how we live and think. If enough of you show up, I’ll run these more often and rope in special guests. Eventually we might even do this in the real world! It’s our little way of fighting back against the growing loneliness epidemic.

In the meantime, I’d love to hear what topics you’d want to tackle, plus any other thoughts you might have.

Looking forward to seeing (or hearing) you at our first session!

Got questions or comments? Leave them here.

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Let’s talk about clickbait.

I’d like to tell you I’m above it. That I can spot the trick from a mile away and scroll past, while lesser mortals click. But I cannot. Every day, we lose eight minutes of our life to clickbait. That’s nearly six months of our life. Actually, I just made that number up.

But regardless of the actual amount of minutes wasted, they are regrettable. And whenever I fall for it, I judge myself for it. I suspect we all do.

We know better, and yet we can’t help it.

That’s because the reason that we’re so easily caught up by it isn’t necessarily that we are stupid, careless or gullible. It’s because we are curious and human. In fact, that’s the core mechanism that the, um, ‘fine purveyors of clickbait’ rely on.

There’s a gap between what we know and what we don’t know, and the brain has a cognitive itch to close it. Behavioral economist George Loewenstein’s research on ‘information gap theory’ in his 1994 paper, The Psychology of Curiosity, found that curiosity is triggered specifically by an awareness of missing information, not by the information itself. “You won’t believe what happened next” creates the gap without giving you anything to satisfy it, so the only way to close the loop is to click. It’s uncomfortable not to know WHAT REALLY HAPPENED NEXT.

We are also wired for loss aversion. Missing out is seen as a threat, even if we realize the answers are not likely to bring us much satisfaction. Which five mistakes ARE we making? What’s that one thing that everyone gets wrong? What is your doctor not telling you?

We can’t help but want to know what’s missing.

According to Kahneman and Tversky’s Prospect Theory losses feel roughly twice as powerful as equivalent gains. This includes informational loss: not knowing something feels like a deficit we’re particularly motivated to fix.

Evolutionary scientists would also suggest that we have an innate negativity bias since for much of human history the cost of not responding to potential threats was high. It’s better to pay attention to a false alarm than be caught up in a dangerous environment. Today, our nervous system continues to pay attention to anomalies—even if they come in the form of listicles that purport to tell you the “SHOCKING truth about…your dog.”

Clickbait headlines are designed to be processed quickly and emotionally, not analytically. A large study of New York Times articles found that emotionally charged content was more likely to go viral. According to the study content that “evokes high-arousal positive (awe) or negative (anger or anxiety) emotions is more viral. Content that evokes low-arousal, or deactivating, emotions (e.g., sadness) is less viral.”

Because it bypasses the cognitive processes that slow down our intake of information, our response is more automatic, reactionary, and emotional.

The skeptical part of our brains isn’t being welcomed in.

Headline writers, advertisers are particularly good at figuring out what triggers people to click. When I worked for an ad agency, I was told that people were more likely to click on odd numbers (eg. “7 ways to improve your life”). Apparently, their asymmetry grabs our attention more than even ones.

But recognizing the techniques will not necessarily inoculate you against them due to a psychological framework behavioral economists refer to as dual-process cognition. According to this theory, we operate in two modes:

System 1: The intuitive system. It’s automated, instant, emotionally responsive, and requires little effort.

System 2: The analytical system. It requires analysis, conscious mental efforts, reasoning, and operates more slowly, objectively, logically, and deliberately.

We rely on both systems in our daily lives—and both can be useful. System 1 allows us to respond to situations quickly and without constantly overloading our cognitive functions. It relies on mental shortcuts and it’s often effective. But certain situations require System 2, particularly when accuracy is particularly important.

If someone comes at you with a knife, you want to go with System 1 processing. When you’re trying to make a key decision for your business or life, you’ll probably want to go with System 2.

Clickbait is designed to trigger System 1 only.

So if recognition alone isn’t enough, what will help you bypass clickbait and System 1 activation?

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I’ll be honest: I’ve never been a good sleeper. For most of my life I was a committed night owl, deeply resistant to anything resembling a consistent bedtime. But I’ve been working on changing my habits lately. Because as any MD will tell you, basic as it is, sleep is one of the most important things for your health. And yet so many of us struggle with it.

That’s why I decided to talk to Mikael Kågebäck, Chief Technology & Product Officer at Sleep Cycle, a company that uses AI and signal processing to help people sleep better.

We talked about what sound can tell us about our health, why sleep regularity matters more than most of us realize, sleep patterns around the world, whether obsessively tracking your biometrics might actually be making things worse (yes, for some of us), and what it means that a handful of tech companies are now sitting on some of the most detailed population health data in the world.

Kågebäck started out as a software developer, then worked as a software architect, before going back to school to do a PhD in machine learning, with a focus on language and NLP. He has spent the last several years at the intersection of AI and sleep science, helping build Sleep Cycle from a smart alarm app into something quite interesting for public health. The app not only tracks sleep, but also managed to predict flu waves two weeks before the CDC did. And it may soon be able to screen for sleep apnea from your phone’s microphone alone. All of this by simply listening to you breathe.

It’s a conversation that starts with sleep and ends up somewhere much bigger.

PS. If you want to try it, Sleep Cycle is free until August 31.

Want to listen only? Find us on Spotify and Apple Podcasts.

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Recently, I managed to lose all of my credit cards.

Yes, all of them.

Suddenly, I found myself cut off from the modern world’s greatest luxuries: public transit, alcohol, and Starbucks*. Also, you know, food.

(*Just kidding. I hate Starbucks.)

I couldn’t even pay for parking and had to resort to the old-and-reliable method of praying that the parking meter person doesn’t come by. It’s not like I had a choice.

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You’ve heard of “woke,” “right wing woke,” and “woke reich,” but there’s yet another kind of woke in town, “dark woke.”

All of these labels share the same DNA. They're reactionary in nature. Each one is a backlash to a backlash.

The original “woke” was a reaction to social injustice, like racism, inequality, and discrimination. It was initially about being alert to these things, but over time the meaning broadened to mean all sorts of different things—positive and negative, depending on who you ask and what mood they happen to be in.

The “Right Wing Woke” (which I had previously written about here) flipped things around. It took the grievances and victimhood that the right had spent years mocking on the left and rebuilt it in their own likeness: virtue signaling, moral absolutism, social enforcement mechanisms, cancel campaigns, and tribal loyalty tests—just aimed in the other direction.

“Woke reich” narrowed the target further, used mainly to describe a slice of the right accused of flirting with extremism, isolationism, and antisemitism.

Enter “Dark Woke”

But yet another variation has emerged: Dark Woke.

Although this phenomenon isn’t some formal ideology, it has been predominantly embraced—informally—as a communication style by progressive commentators and figures in a highly polarized environment. It’s a more cynical, combative style that rejects traditional liberal politeness in favor of aggression and meme-driven confrontation towards those that they view as their political opponents.

But even that is a sequel of sorts, often compared to the “dirtbag left”—a phrase coined in 2016 by writer and Chapo Trap House co-host Amber A’Lee Frost to describe a strain of socialist politics that treated politeness as a tactical liability rather than a virtue. Vulgarity, Frost argued, is “the language of the people,” and the left should be willing to use it. This style of political discourse consists of irreverent and crass humor, anti-establishment rhetoric, frequently used to skewer establishment Democrats/centrists and even aspects of activist culture, not less harshly than conservatives.

However, while the dirtbag left was more explicitly rooted in economic populism and class analysis, “dark woke” is perhaps better viewed in the context of being a direct response to the Trumpian politically incorrect style employed by MAGA.

Indeed, the hashtag #darkwoke started circulating on X around Donald Trump's second inauguration, with left-leaning accounts sharing memes that gleefully imagined Trump supporters' comeuppance.

Soon Democratic candidates were encouraged to use a more combative, profanity-comfortable rhetoric to win back voters drawn to Trump's bombastic style.

Democratic communications consultant and former digital director for the Wisconsin Democratic Party, Bhavik Lathia, told the New York Times: "Republicans have essentially put Democrats in a respectability prison."

She continued: “There is an extreme imbalance in strategy that allows Republicans to say stuff that really grabs voters’ attention, where we’re stuck saying boring pablum. I see this as a strategic shift within Democratic messaging — I’m a big fan of ‘dark woke.”

California Gov. Gavin Newsom’s launched a meme warfare campaign, engaging in Trump-style trolling.

Instead of the high road: persuasion, compromise, "finding common ground," under “dark woke” the goal is to out-dominate the other side. Outrage gets met with bigger outrage. Insults get answered with sharper insults—and memes. The political correctness the left once policed gets thrown out the window too. If certainty, anger, intensity, resentment, and cruelty are what’s winning on one side, deploy the same toolkit on the other side.

“The idea is to subvert the qualities that people think made wokeness cringe—the virtue policing, the polite ‘when they go low, we go high’ posturing—and go Joker Mode to Make Democrats Cool Again,” writes GQ’s Kieran Press-Reynolds.

When your audience has been desensitized to the point that they respond to shock value over nuance, where else can you go?

The central thinking is this: If your opponents have spent a decade getting rewarded for cruelty, refusing to be cruel back just means losing politely.

As with many movements, it is justified since it’s for the greater moral good.

The Strategy: Out-Cruel the Opposition

Is it an effective political tool? Probably. Stepping outside of political correctness was part of Donald Trump’s appeal with many of his voters. Crass is seen as authentic. So is trading insults, not holding back. The “dark woke” are simply embracing that for their own ends.

Perhaps it’s also appealing to those observing because it gives them a sense of empowerment: “Aha! He really told him off.” They live vicariously through the insults they might be thinking but are perhaps unable to deliver directly. That’s energizing for supporters.

“The other side did it, so now they get a taste of their own medicine,” is a sentiment I’ve often heard echoed on the right spectrum. Now the same is being spoken by the left. Ultimately, this is less ideological than psychological. It’s about power, ridicule, anger, and revenge.

Attention vs. Action

But while outrage is good at getting attention, it won’t get people to act: naming the villain will.

A 2021 PNAS study analyzing over 2.7 million social media posts found that the strongest predictor of how far a post traveled wasn’t emotional language, but rather naming and attacking a political out-group. Another recent study tracked over a million posts linked to nearly 25,000 Change.org petitions and found that posts expressing moral outrage tended to go more viral, but didn’t make a particular difference to whether anyone actually signed the petition being promoted.

The findings stated that in “expressions of agency, group identity, and prosociality were associated with more signatures but no more virality.”

The Cost

But when you name your enemy and target them as such, dehumanization cannot be avoided. It is difficult to strike as hard as “dark woke” seeks to without flatten them into a caricature first. It’s a necessary coping mechanism for those intent on delivering blows.

But, of course, all of this simply leads to escalation and greater polarization, which—after it reaches a certain point—it might be impossible to come back from. We can end up in a state of permanent hostility.

Research consistently shows that as people become more ideologically divided, not only do they become more distant and dislike each other more, we are more likely to “participate in extreme forms of outgroup derogation.”

The Feedback Loop

Throughout history, reactionary movements have often absorbed the traits and tools of their adversaries, creating a sort of self-perpetuating loop: defeat your opponent by becoming more like them. If they don't resemble their opponents in ideology, they often come to resemble them in behavior. Even movements of counterculture eventually curdle into their own brand of conformity. Anti-establishment movements build their own establishments.

And, as they say, if you fight fire with fire, eventually everyone gets burned.

Means, Ends, and Tradeoffs

Proponents of the “dark woke” approach view responding to aggressive tactics with polite discourse as a failure. The Michelle Obama sentiment of “when the go low, we go high” is seen as ceding ground, a naive approach. If someone is pointing a gun at you, the thinking goes, you don't talk, you point one back. And be willing to shoot first.

But do the goals matter less than the methods by which they are achieved? If you abandon the moral high ground to win, what exactly have you won besides the power itself? If you adopt your opponent’s rules, methods, and cruelty, what’s left to distinguish you from them—besides which letter follows your name on the ballot?

The two sides don't want the same things, and that's an important distinction. They are not interchangeable. But these questions aren't about which goals deserve to win. They're about what you become once you reach for corrosive methods to get there.

Is it possible to win without doing any of this? It’s hard to know. Although for years, in many countries, parties have won and lost elections without…going low. It seems possible, even if the current climate has shifted.

But ultimately “dark woke” rests on a quieter assumption about the people it’s trying to mobilize: that winning matters to them more than how the game gets played. That might be true. It’s also exactly the bet the other side already made.

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