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This story appears in our Summer 2026 issue, on newsstands July 28. Want us to come to your place? Become a member to get digital access to the issue and early access to paywalled content. Welcome to Fair Play, a column exploring the shifting dynamics of sex, dating and culture by Playboy Senior Editor Magdalene Taylor.
This story begins in an Eataly. Amid the rows of jarred syrupy cherries and laughably priced pastas, I meet Adam. Adam is a bachelor. He is 34 and the CEO of an industrial tech company. He lives alone in the West Village. He votes Democrat. He reads books and writes in a journal. He meditates. He is good-looking and six feet tall.
Dating, Adam tells me, is like dipping one’s toe into the water to gauge the temperature and having one’s foot ripped off by the force of the current. Which is to say, maybe he is not that good at it, maybe it is not even all that pleasant, but he is, at least, in demand. Very in demand.
Such is the condition of the New York City bachelor. Is it unfair or dishonest to make sweeping claims about the state of American masculinity and focus my sample exclusively on the men of the United States’ largest metropolitan area? Perhaps so. But it is here, one could argue, that the 20th-century ideal of the bachelor was cemented: the kind of guy who wears a suit to work most days, owns plenty of leather furniture in his high-rise apartment, and has enough disposable income to buy, well, whatever the hell he pleases. The real defining characteristic of New York City as a place of romantic optimism for the bachelor is its gender ratio, which, anecdotally, skews two single women to every single man in several neighborhoods. As Lana Li, a writer and data scientist, explained in a March 2025 post on her Substack, Love Me like a Robot, using data from the American Community Survey, there are 20,000 more unmarried, college-educated women than men in Manhattan. The result for men, she writes, is “an embarrassment of riches,” making New York “the Valhalla of young, single men.”
The average bachelor today, however, might relate more to the Spartan tradition of classical antiquity in which unmarried men were forced to march naked through the streets in winter singing songs of self-ridicule, or the festival in which married Spartan women could drag single men around an altar and humiliate them with thrashings. Every headline about the state of the young male today suggests the spiritual equivalent of such a fate. Young men are increasingly underperforming their female peers in educational attainment and income. They are more likely to live at home with their parents, and a growing chunk of them are not dating at all and never have. Many of them are not only unemployed but are also not even looking for a job. Suicide is the second leading cause of death among men ages 25 to 34. Unintentional injuries, including drug overdoses, are the first.
But not all hope is lost. Truly. Average men with jobs and friendships and desire to date exist. And they’re relatively happy. Maybe that does not sound like you now. Maybe you are a young man, beginning what should be a period of prosperity in your life at a time of economic and political upheaval. Maybe it seems like you came in at the very end of something. You’re not wrong at all to feel that way, but let one thing be known: You, too, can find the life you want.
If you shower and are a decent person, if you have a job, if you have a place, a bed frame—the standard is so low and so easy to meet.
Elliot, 38, nonprofit office manager
Elliot, 38, is another guy doing well. He has his own apartment and a full-time job at a prominent nonprofit. Still, he is sure he’d find romantic success with less.
“What I’ve told my friends, who are also bachelors, is that if you shower and are a decent person, if you have a job, if you have a place, a bed frame—the standard is so low and so easy to meet, it’s really sad and pathetic if someone feels like they’re lonely outside of their own choice,” he says.
Now maybe if you’re of a different generation, 34 and 38 sound a bit old for bachelorhood. And indeed, historically, it somewhat is. The earliest mentions of bacheler date to the late 13th century, when it meant a knight with no vassals, followed shortly by its appearance in Geoffrey Chaucer’s Canterbury Tales in about 1386. There, Chaucer introduced a character known as the Squire. He is described as the son of a knight, about 20 years in age, “with lokkes crulle as they were leyd in presse,” locks so perfectly curled it looks as though he wore them in curlers. He is of moderate height, agile and strong, and knows how to compose songs, draw, and write. He is courteous and humble. He is so full of love and life in hopes of standing “in his lady’s good graces” that he barely sleeps at night. He’d probably love an Eataly.
For centuries, the term bachelor held this juvenile, entry-level positioning of a young man without much to show on his own. A bachelor’s degree, for example, was first awarded to young scholars, junior guild members, and monks eligible to continue on to higher education after their first round of studies. It wasn’t until the Victorian era that bachelorhood took on a connotation of romantic eligibility. From the 1800s onward, to be an eligible bachelor meant that you were not only single but also of solid-enough financial standing to properly support a wife and family.
From there bachelorhood became something of an aspiration—one, it could be argued, that serves as the ideological foundation of this very magazine. You imagine a man in his warm, expansive apartment overlooking the city, placing the needle on a record as he pours himself another scotch. Each weekend, a new woman joins him in the conversation pit. In September 1956, Playboy commissioned a multipart illustrative series on the idealized “penthouse apartment of the urban bachelor—a man who enjoys good living, a sophisticated connoisseur of the lively arts of food and drink and congenial companions of both sexes.” His domain includes a dining room larger than the average studio apartment.
In the contemporary context, Adam might sound like an outlier. Elliot, with his Manhattan apartment and principled job, might too. But there are also guys like Jon, 29, who bartends in Greenwich Village and lives with roommates in Astoria, fitting the profile of a single guy doing just fine.
Jon is not on any dating apps. Being a bartender in a big city where women like to drink, you don’t really need them. He’s not quite bringing home the women from work, though he’s had some offers, but being a bartender begets meeting other bartenders. Many of the people he hangs out with, platonically or otherwise, are in the service industry themselves.
Jon has always had somewhat of a knack for talking to girls in person, perhaps the same knack that makes him a good candidate for bartending. From his first nights out at 21, he was always the most gregarious of his group.
“I remember going out with friends and thinking, ‘This is gonna be fun. We’ll get to talk with people.’ But being around my friends who were more shy, it was very eye-opening for me. One night we got to this bar, and there’s like a bunch of people dancing. I saw this one beautiful girl, and I’m like, ‘I’m gonna go dance with her. Why not?’ And all of my friends said, ‘Yeah, there’s no way.’ ” But their doubt only motivated him. “I said to her, ‘I can’t believe you were dancing alone. That’s so crazy.’ She’s like, ‘Yeah, people asked me, but you’re the one that made me feel no pressure.’ It was just super easy.”
“People really want to talk about themselves, and it’s really hard to listen.”
Jon, 29, bartender
For Jon, approaching women is as simple as being casual and respectful. It’s something that takes practice and something he has indeed failed at too. “I’ve totally bombed so bad before,” he says. “I have a big rule now: Never approach a girl reading a book at a bar. I am never ever doing that ever again.”
On a recent Friday evening, I visit Jon on his shift at & Son, a bar and steakhouse that makes its employees wear suspenders. After work, Jon joins me at a nearby bar popular with fellow bartenders. There, he is greeted and hugged by multiple women. It occurs to me that it might look like I’m his date and I am therefore probably cockblocking him. As we chat, Jon reiterates to me that his strategy for meeting women and being social is relatively simple: You just keep working it. You just stop being weird. You just keep asking questions. All this, he says, he has learned mostly from his job. “People really want to talk about themselves, and it’s really hard to listen,” says Jon. He wins in this world by being someone willing to listen.
Politics is, for better or worse, a defining factor in the fuckability of the single young man today. At minimum, showing allegiance to causes of the Left—of which the largest share of young women, 40 percent, are part—helps the case, especially in places like New York. For Elliot, whose app profiles list his workplace as the aforementioned high-profile progressive nonprofit, demonstrating his politics is a cinch. “Is it virtue signaling if it’s true?” he asks of having markers like the Palestinian flag or ACAB in one’s dating app bio. He finds that identifying his politics to women helps them feel safer. “If you can communicate with someone that you’re not a piece of shit, that actually goes a long way when the standards are so low for how dudes present themselves,” he says. Elliot often dates upwards of seven people at a time, keeping them organized with a full Google calendar.
There are times when juggling everyone has gotten him into trouble, say, from a toothbrush left behind or a condom wrapper on the floor. But for the moments of remembering whose sister just got a new job or which movie he saw with which woman on which weekend, he’s got one easy trick.
“How do you get out of it? You just go, ‘Oh sorry, I’m confused.’ Honestly, it usually works out pretty well.”
“I find it to not be difficult,” he says. “What I do find difficult is expectations. If things are moving quickly and I realize that this person isn’t an actual potential lifelong match, then that can get annoying and tricky. Sometimes a person will get to that point very quickly—one week in, two weeks in, two months, whatever it is. There’s this funny balance where you’re open and honest, but you’re also having ridiculously silly conversations early on, like ‘Hey,’ the first date, ‘what are we, what are your expectations, do you want to get married tomorrow?’ ”
For all his dating around, Elliot does have a desire to find something serious. “My wiring lends itself toward wanting monogamy,” he says. Even so, he is happy to accommodate far less serious dynamics, at least temporarily.
I ask him to walk me through his weekend plans: “On Friday, I’m seeing an off-Broadway play with a person I’ve been dating,” a different person than he is going on a date with after we finish our conversation, though he will be seeing her again on Saturday. “On Sunday, I’m seeing someone who has made it clear they are emotionally not available, and it’s sex only.”
OK, OK, so these guys are relatively well liked by women and go on dates and have plenty of friends. Let’s address the real question: What are their sex lives actually like?
Whether a bachelor is looking to settle down or remain single in perpetuity, the entire identity is really more of a polite way of saying a guy is fuckable. The hygiene routine, the nice apartment, the asking others questions about themselves—it would all be for naught if it didn’t yield the belief that sex is more tangible for it. And, yeah, of course it all has other benefits, but there’s no shame in the reality that people, especially young men, do certain things and act certain ways in order to potentially have more sex. That is, ultimately, what a bachelor is.
So, yes, Adam, Elliot, and Jon are all having sex with someone regularly. Elliot is likely having the most, at least in good part because he is actively pursuing it the most. He’s on Feeld, where his profile states an interest in “brats” and light BDSM leanings. Jon, by his own admission, is largely still figuring himself out post-breakup. Sex happens but is not the priority. Adam, meanwhile, is the most coy: He is having enough sex that he doesn’t want to speak much of it. At one point, I press him. “I’ll put it this way: I’m getting everything I want out of my sex life,” he says.
It often feels impossible to analyze the circumstances of contemporary dating without applying economic terms too. Adam does so often. Even the term roster, which he loathes, carries its own connotations of an investment portfolio.
“We just keep using market analogs,” he says to me at one point in our conversation. “It’s a bit like betting on a stock.”
He himself, I must note, does not view women in this way. Rather, he believes that some women might view him as the stock. And he is correct in his understanding of that dynamic.
The comparison was most apt in his 20s. He used to have long hair, living in San Francisco as an engineer for an app you almost definitely have on your phone. At the time, he had a long-distance girlfriend who begged him to cut his shoulder-length locks. When she met him at the airport to move in with him and saw that he hadn’t cut his hair, she cried.
“There’s this funny balance where you’re open and honest, but you’re also having silly conversations early on, like ‘Hey, what are we, what are your expectations, do you want to get married tomorrow?’ ”
Elliot, 38, nonprofit office manager
When they eventually went to visit her family in Chicago, he decided it was finally time to make the chop. As he entered her family home, freshly barbered, he recalls her father, the CEO of a publicly traded company, saying to her, “That’s what I told you. Buy low, sell high.”
“He was speaking market logic,” Adam explains, “implying that she used market arbitrage by finding me with long hair, when I looked less attractive, and then making me get a haircut, but she was actually right. If you do put this in the piece, make sure that I state clearly that I think she was correct. I looked bad with long hair, and she was totally correct.”
Today, though, Adam is indeed something of a catch. He looks a bit like Ron Livingston, of Office Space and the infamous Post-it note breakup with Carrie Bradshaw, and (keeping with the Sex and the City theme) has a terrace that looks out over Sarah Jessica Parker’s. Does he have a roster? At least not one he’d admit to. That would not be dignified.
During our conversation, he pulls out a notebook filled with thoughts about what it really even means to be a bachelor. One specific note he highlights: “Imagine an actually cultivated person talking about rosters or situationships.” Language, for Adam, is critical. No crass jokes. No edgelord humor. Is this the language of a person trying to foster a beautiful life? At your wedding, do you want this to be the first story of you two meeting? These are the questions he believes the prospective bachelor should be considering. Adam has also thought a lot about the definition of a bachelor. He is strict on the idea that a bachelor has never been married, in contrast to our colloquial usage with shows like The Golden Bachelor, featuring divorced and widowed men, and in contrast to Elliot, who has been married and amicably divorced once. But the bachelor is, to Adam, nevertheless a term in relation to marriage: The idea is that a bachelor will one day be married. And while he does want this someday, maybe even sooner than later, he’s again cautious of what this verbiage evokes.
His only hesitancy on marriage, he says, isn’t marriage itself but the way wanting it can sound. There’s an aggressiveness, he feels, in announcing that you are “gunning” to date someone. And if he really analyzed his resistance, it comes down to this: The energy of saying out loud that you’re looking for someone right now can be “kind of wretched.”
He imagines the opposite of himself: someone grinding on the apps, four dates a week. That’s not him. He’s not looking for a girlfriend, and there’s a certain “frenetic puppiness” to the search that he’s pretty sure he doesn’t embody. Yet he does want to land in a relationship that’s ultimately serious: in love, married, maybe a family. He once thought he’d have all this by the time his parents did, at 35. As that age rapidly approaches, though, he’s accepted that the horizon may indeed be a bit more distant. There’s a good way to go about achieving that status, he says, and a bad one. Dwelling too much on age is, for him, a bad one.
Perhaps here is a good place to mention that Adam is becoming a practitioner of Zen Buddhism.
“I don’t know if I’m the ideal bachelor,” he tells me as he combs through his notes, reflecting on why he agreed to let me interview him. “It’s not something I’ve necessarily aspired to in my life, to be a bachelor at 34. It actually kind of implies a set of relationship failures, but I think when you told me about this piece, my thinking about it was that there is this cultural thread of a bachelor in American society.”
Adam wants to think about what it means to be a bachelor, just as I do, in order to consider what good the role might offer young men today: “If we pick up that thread and men try and cultivate themselves in a nontransactional way, not thinking about their marketplace value but as human beings, we can get back to a dating dynamic that’s more romantic, and I think that’s a really powerful concept.”
Not just powerful, he says, but masculine. Healthy and masculine.
Adam likes to imagine young men having their A Summer’s Tale moment, referring to the 1996 Éric Rohmer movie about a young man who begins his summer going after a girl who isn’t interested in him—before finding himself chased by several others.
You might spend your 20s confused, desperate, and awkward, but that’s OK. The point, Adam says, is to continue to cultivate yourself: to find the things you genuinely care about, to respect both yourself and others. At some point, maybe not until a man reaches his late 20s or early 30s, the pieces will fall into place. “I think any guy—no matter how you look, no matter how you are—if you take care of yourself, a lot of men can have their A Summer’s Tale moment,” Adam says.
Adam wants other men to know they can have what he has, regardless of the CEO title or $7,500-a-month apartment in one of the most desirable neighborhoods in the world. If one can cultivate an eye for beauty and a sense of confidence in oneself and romance, he says, “they might just be a perfect bachelor. They might even be a perfect bachelor just to one person.”
And, yeah, being in New York might help. But a life of hobbies, interesting people, and self-worth can be grown nearly anywhere in this country. It’s just a matter of choosing to do so. Take a deep breath. Turn off the manosphere podcast. You’ve got time.
