Why Are “Troubled Guys” So Popular in Tokyo at Night?

In Tokyo at night, there are winners who defy the conventions of daytime life. To an outsider, they come across as arrogant. They’re a bit ridiculous, and sometimes even dangerous. Yet, for some reason, women are drawn to them. Nishi-Azabu, Roppongi, Sangenjaya, Nakameguro, Kabukicho, Kamata.As you move from one neighborhood to another, the looks, behavior, and aura of the men who are popular with women change. Tokyo isn’t so forgiving that a man can be popular just by looking good. So, what kind of man is actually chosen in Tokyo at night?

The Winning Strategy for Popularity in Nishi-Azabu and RoppongiBeing rich is just a prerequisite. What matters is the scent of tangible benefits.“Ah, in that case, I’ll handle it.”

When it comes to Nishi-Azabu and Roppongi, there’s a deeply ingrained image of these neighborhoods as places where up-and-coming entrepreneurs who spend money like water cross paths with beautiful women drawn to that wealth.In fact, the men who gather in these neighborhoods clearly have more money than the average person. However, since everyone around them is equally well-off, being rich in and of itself isn’t a decisive differentiator anymore. These days, it’s practically just a prerequisite.

In the past, in Minato Ward’s nightlife scene, aspiring models and actresses seeking a foothold in the entertainment industry or connections with people in power tended to work discreetly in lounges or go out drinking with industry insiders. It was a place where men who otherwise had no way of meeting such women crossed paths with them. That exclusivity and rarity were what sustained the neighborhood’s value.

However, as “paid drinking” became mainstream through apps, the pool of women drinking in Minato Ward expanded. If a woman becomes popular in the nightlife industry, she can earn more than the average top-tier corporate employee. Through social media, it’s also possible to gain recognition and secure work without relying on powerful figures or sponsors.As a result of women gaining money and influence on their own, a man’s financial resources or title alone are no longer enough to be a decisive factor.

So, who are the powerful men in Nishi-Azabu and Roppongi today? They are men who seem likely to deliver concrete benefits in the short term—men who can take you to exclusive venues normally off-limits to the public, or introduce you to influential business executives and entertainment industry insiders.He has connections that lead to job opportunities and media exposure. Simply posting a photo of you together on social media can rack up “likes.” In this neighborhood, what matters isn’t so much what a man has, but what those resources can offer a woman.

The fact that cosmetic surgeons have been making waves in this area lately can’t be explained solely by their high annual incomes.There’s even a chance to get popular procedures for free. For women whose investments in beauty translate into social media success, career opportunities, and popularity, there’s probably no benefit with a faster payoff than this.

A man who seems like he could change things starting tonight is more appealing than one who might provide for you in the long run.It doesn’t matter if he’s a business owner, someone in the entertainment industry, or a doctor. What’s important is that he appears capable of converting his money, connections, and title into something beneficial for her.

Of course, he doesn’t even need to actually give her anything. If he can make her think, “If I stay on good terms with this guy, something might happen,” through social media posts or casual remarks in conversation, that alone increases his value.

In this city, everyone from the founders of publicly traded companies to con artists sits side by side with the same expression on their faces. There are genuine successful people, and there are men whose job seems to be mimicking them. At nighttime gatherings, it’s not so much whether someone is the real deal or not that matters—it’s the sense that they might be able to make things happen that’s valued first.

“Ah, in that case, I’ll take care of it.” A man who can say that line with a slightly languid air is a strong one. Can he really pull strings, or does he just know the other person’s name? That’s no longer the issue. What matters is whether he can make you believe that something is about to start moving in your favor.

The Winning Strategy for Popular Guys in Sangenjaya and NakameguroThe Status Battle Among Natural Wine Guys.“I’m kind of over the whole Minato Ward and Shibuya vibe.”

A strong man in Sangenjaya and Nakameguro is one who can pull off a look that shows he looks down on the game of financial clout. Right in the heart of Minato Ward or Shibuya, the hierarchy based on financial clout, looks, and fame is blatantly obvious.Instead of competing head-on there, he puts on a face that says, “I’m not interested in places like that.” He’s skilled at making it seem like he’s not just stepping out of the competition—but that he never had any interest in the first place.

Whether it’s choosing a restaurant, talking about music, or complimenting women, that attitude remains consistent. He doesn’t jump at obviously expensive places.He shows no interest in hit songs everyone knows. He doesn’t blatantly praise women who are obviously beautiful to anyone. He intentionally hints that he’s the kind of man who can find value in things that are a little off the beaten path.

The women in this city, too, are somewhat jaded by the game of competing on youth and looks right in the heart of Minato Ward or Shibuya. But they don’t want to think of themselves as having lost.They don’t compete in the “obvious beauty” category, but as women, they still want to win in their own way. They want a man who finds their conversations interesting, appreciates their slightly quirky hobbies, and notices the subtle, understated allure they possess—even if it’s not flashy. A man who picks up on those qualities and says, “That’s exactly what I like about you,” is the one who really resonates with them.

To give a clear example, a typical figure making waves in Sangenjaya and Nakameguro is a restaurant owner who once worked in the film, music, and fashion scenes and has now opened his second location. Stylists, filmmakers, people in the apparel industry, and up-and-coming actors drop by his place casually.Rather than being a “high-flyer,” he’s a man who has his finger on the pulse of the neighborhood. While the Minato Ward guy uses money and connections to project an air of superiority, the Sancha-Nakameguro guy projects a sense of belonging to a stylish neighborhood simply by being a regular at a spot where such industry insiders drop by.

However, the depth of that culture is questionable. Whether it’s music or movies, their discussions are closer to self-promotion than criticism. Their understanding is often so superficial that the moment someone who’s truly knowledgeable shows up, they immediately switch to just nodding along.

“I’m kind of over the Minato Ward and Shibuya scene.” Have they truly grown tired of it, or have they simply moved to a place where they can hold their own?Even he himself doesn’t know the answer to that anymore.

The Winning Strategy for Popularity in KabukichoThe War of Attrition in the Underground World of Hosts Who Lure Women into Their Swamps. ‘I’m a piece of trash, but you like that kind of thing, right?’

What makes Kabukicho unique is that the status symbols of mainstream society don’t apply at all.In Nishi-Azabu and Roppongi, money, connections, and titles define a man’s worth. In Sangenjaya and Nakameguro, belonging to a trendy scene makes a difference. But in Kabukichō, neither of these factors is a decisive factor. At the top of this neighborhood’s popularity hierarchy are host club hosts and underground male idols.

Why does this status reversal occur? It’s because what’s sought in Kabukichō isn’t social advancement, but emotional connection. Men valued in daytime society are stable, responsible, and have a promising future. But in the nightlife of Kabukichō, that stability seems all the more distant.What women want isn’t a sincere man. It’s a man who seems to single her out from the crowd. A man who shows his vulnerability. A man who stirs up a woman’s emotions.

In other words, in Kabukichō, the popular guy right next to you is more powerful than the successful guy far away. No matter how popular they are, hosts and underground male idols aren’t as distant as celebrities.You can go see them. You can talk to them. You can be recognized by them. But they aren’t quite as close as an ordinary person either. Somewhere between that closeness and that distance lies the “swamp” of Kabukichō.

Given the same looks, in Kabukichō, a man with the title of “host” or “underground male idol” carries more weight. That’s because titles—which don’t necessarily inspire trust in the “daytime” world—become a way to visualize popularity in this neighborhood.Bookings, sales, lines for photo sessions, comment sections, social media reactions. The more visible it is that someone is being supported, the more attractive that man appears. Rather than his individual charm, a man’s value swells precisely because he is “in demand.”

“I’m a piece of trash, but you like that kind of thing, don’t you?” That single line resonates in this neighborhood.Whether he’s truly a scumbag or if those words are simply a result of adapting to the city is no longer the issue.

The Winning Strategy for Popularity in KamataThe Aftermath of ‘Which Middle School Did You Go To?’: The Hierarchy Established by Middle School Lasts Forever

The men who thrive in Kamata aren’t those just starting their careers.They’re men who’ve always given off an air of strength. In Minato Ward, you can project an air of superiority with money and connections. In Sangenjaya and Nakameguro, you can project the image of belonging to a trendy scene. In Kabukicho, you can stir up women’s emotions by being a local celebrity. But in Kamata, acquired sophistication alone is unlikely to be the deciding factor.What counts in this neighborhood is the credibility of a man who hasn’t been looked down upon by the locals.

In Kamata, a man’s worth is measured by how well he holds his own locally. You can usually tell who he is—before he even says a word—by the reactions of those around him. Who approaches him?Whose protégé is he? Has he always had no trouble with women? Is he the one who gets treated roughly by his peers, or is he at the center of the group? Information that might seem trivial in the city center directly translates into a man’s credibility in this neighborhood.

What the “gal”-style women of the downtown area are looking for isn’t whether a man can take them to a higher social circle. Nor is it whether he appreciates their sense of style.Nor is it whether he’s a popular guy who stirs up her emotions. It’s whether he’s a genuinely strong man within the community where she lives. Being with him means she won’t be looked down on in the neighborhood. If she introduces him to friends, they’ll get it with just an “Oh, that guy.” When trouble arises, he gives off the vibe that he’ll step up without backing down and settle things. That kind of straightforward strength is what counts in this neighborhood.

To give a clear example, the typical guy who’s a big shot in Kamata is a local who runs a business—whether it’s an interior design firm, a plumbing company, a car dealership, or a restaurant—and who takes good care of his juniors, both at work and when they’re out drinking. Whether it’s at an izakaya in front of the station, a local festival, or the after-party for a friend’s wedding, he’s somehow always at the center of things.Even if he doesn’t say much himself, the reactions of those around him explain his standing.

That’s why a conversation that starts with the question, “Which high school did you go to?” isn’t just small talk about the area. It’s about which generation he belongs to, who he knows, and where he used to hang out back in the day.It may seem like they’re just chatting and laughing, but what’s really happening is a credit check and a confirmation of social standing. In just those few minutes, the man’s “resume” is largely laid bare.

“Which middle school did you go to?” That single phrase not only opens up the other person’s “resume” but also reveals one’s own. It’s a question you can only bring up because you’re prepared to be judged yourself.

Editorial Department, Mitsui

I’ve been spouting all sorts of half-baked theories with a cynical attitude up to this point, but these guys are the “winners” who are genuinely popular in their respective cities. Ultimately, I’d like to confess that it’s actually me—the writer observing all this from the outside—who is the type who is overwhelmingly unpopular no matter which city I go to.