How Do You Explain Zayn? The 25-year-old British singer is deeply, maddeningly, almost trolling-ly enigmatic. And that cultivated mystery—along with his disdain for the standard rules of superstardom—is probably what puts him on the short list for COOLEST HUMAN ALIVE. On a recent Friday night, though, he dropped his guard and spilled his guts.

There are exactly two places in New York on a Friday night where Zayn Malik can smoke Marlboro Lights as liberally and openly as he pleases, unencumbered by gawkers or the city’s increasingly draconian anti-smoking laws. The first is Zayn Malik’s SoHo apartment, where he spends the majority of his time, zoning out, reading books, listening to music, and “partaking in the herb,” as he says. The second is the Mary A. Whalen, a 172-foot-long restored-tanker-ship-turned-nonprofit-hangout-spot that is docked off the shore of Red Hook, Brooklyn. The ship is closed for business after 6 P.M., but tonight its leader, a hardy blonde ship preservationist named Carolina, has agreed to keep it open late to accommodate us. No crowds, a few plastic chairs, and a gently lilting surface that is basically a giant ashtray.

There is just one problem: The temperature on deck is decreasing rapidly with the setting sun, and Zayn—the 25-year-old former British-boy-band member, current solo pop-ish star, and all-around inscrutable avatar of contemporary celebrity—has arrived with nothing on his person but a lighter, a backpack, and an iPhone. No jacket on his rail-thin five-ten frame—just a pair of charcoal skinny jeans, a distressed Pink Floyd T-shirt, a bright pink beanie that obscures his new flower skull tattoo (or “tah-oo,” as Zayn pronounces it). He looks so modernly cool, blending a hip-hop swagger with a punk-rock edge, that he should receive a cut from Urban Outfitters every time someone makes a purchase. He is the only man whose Disney-princess-long eyelashes seem to bolster his machismo rather than diminish it. Nobody this dreamy has ever bothered to check the weather to see if he should grab a jacket before leaving the house. Through chattering teeth, he rejects multiple offers of blankets. “It’s all good,” he insists, burping faintly after taking a swig of his Peroni. “I’m cool.”

Still, Carolina avails us of the ship’s warmer galley. “I might have a cigarette first?” Zayn asks, as though he needs permission, gesturing toward the other side of the ship. Over there is his assistant Taryn, a young woman with French-braided pigtails that make her look more like a high school soccer player than someone designated to manage the everyday logistics of a notoriously slippery superstar’s life. She is the custodian of his pack, doling out individual cigarettes to Zayn periodically.

But Carolina assures us Zayn will not have to stay outside to smoke his cigarette. She’ll let us smoke belowdecks on the condition that Zayn provide her one of his Marlboros and permission to snap a photograph. She promises she won’t post it until after the story runs. “Uh…yeah?” Zayn replies, sounding sincerely surprised that he is the one who has to answer a question that was directed at him.

A steely detachment from life’s mundane logistical concerns is part of almost every celebrity’s existence, but it is the core of Zayn’s being. This character trait has ruinous potential, but it also means he gets to live his life exactly how he pleases. And it means that he doesn’t have to express a single word or hint of desire in order for the conditions around him to re-arrange to his liking and comfort. There’s a hapless Peter Pan quality to it that makes it tough to hold against him.

We settle around the table in the ’70s-style kitchen on the boat. It’s 15 degrees warmer down here and private. Zayn instantly appears relieved, his shoulders unclenching and his brow de-furrowing. He stops shivering. He is in a womb-like space, drinking beer and smoking cigarettes, and he seems palpably and unexpectedly happy. “Thanks,” he says quietly and earnestly in Carolina’s direction as she seals off the door behind us. “Couple of times I tried to quit. But I just like smoking cigs. Simple as that.”

There is a major conundrum in Zayn’s life, which is that he may be constitutionally incapable of being a star. He tells me so almost immediately. “I don’t work well in group situations, with loads of people staring at me. And when you say ‘star’…everyone wants you to be this kind of character that owns a room or is overly arrogant or confident. I’m not that guy,” he says. “So I don’t want to be a star.” Zayn seems to aspire to the soul of Prince, or some cult ’90s skate-punk figure, but is trapped in the trajectory of a Justin Timberlake.

A decade ago, someone like Zayn would not have become the Chosen Member of a band like One Direction. The Chosen Member is the boy-band graduate whose solo career evolves and hurdles into grown-up relevance, ultimately overshadowing the band’s legacy. Until recently, you could spot a Chosen Member from a mile away—he was unequivocally the best dancer and the one the most girls wanted to bring home to their parents. But Zayn never fit the mold of a Chosen Member. From the day One Direction formed, on the U.K. show The X Factor in 2010, he was cast as the smoldering background foil to the eager-to-please Harry Styles and Liam Payne. His energy and his dance moves were muted. He presented as the quiet, disillusioned one.

But in the past five years or so, it has become acceptable—necessary, even—for a young pop star to show some edge. Thanks to the social-media-fueled, ever intensifying quest for authenticity, real or feigned, we no longer expect our most famous musicians to be toothless and virginal robots. Now we demand that they show a certain degree of lustiness, instability, anti-heroism. The Weeknd scored a No. 1 hit with an elaborately coded song about a cocaine binge—and then followed it up with another No. 1 hit, this one explicitly referencing a cocaine binge. Lana Del Rey’s entire aesthetic revolves around a kind of narcotized death wish. And Taylor Swift spent her last album desperately trying to persuade us that she really is villainous. Even Disney’s babiest-faced of pop princesses, Selena Gomez, is getting mileage out of her demons, playing a Girl, Interrupted–style heroine and rocking a hospital bracelet in a music video. Face tattoos are basically required for entry onto the Billboard Hot 100 these days. Squeaky-clean is no more. Tattoo Numbing Cream is probably a must when it comes to sensitive areas.

And yet even for the most tortured-seeming of these artists, there is still a fierce expectation that they play the game. Mild drug habits or mental illnesses are perfectly acceptable, so long as someone is willing to write catchy songs about those tendencies and then later gussy them up for arena audiences and gamely field jokes from talk-show hosts. Even Justin Bieber, the poster child for our current era of troubled pop stars, is always just one phone call with his pastor away from being able to quiet his demons and pop-and-lock on demand.

Zayn seems like a perfect avatar for this new generation of bruised pop heartthrobs, but he’s the only one of his cohorts who can back it up with a sincerely jaded disposition and an unpredictable way of being. He is the only one who is staunchly unwilling to play the game. You will not find Zayn cheesing with a random group of famous people for someone’s Instagram story at Coachella, nor will you find Zayn learning the latest viral dance move with Ellen DeGeneres. When he released his solo debut, Mind of Mine, two years ago, he opted out of touring altogether, surely pissing off a bunch of emotionally and financially invested parties. And although he promises to be more public-facing this time around—he insists he will tour—he’s still removed from the album-cycle content churn. He says the creators of Atlanta have reached out to him to appear on the show—a dream opportunity for anyone in the music industry at this moment—but persnickety Zayn is still mulling the potential. “If the part’s right, I’d be really into it,” he says. Even the “behind-the-scenes” video that accompanied his new single fails to actually take anyone “behind the scenes”—it’s just the song playing over some B-roll. “I guess the cameraman didn’t get too much footage,” Zayn says on the boat. “I might have been running away from him a bit.”

When I ask him why he failed to show up at the Met Gala a couple days earlier, he almost chokes on his cigarette smoke as he exhales. He went to the Met Gala once, in 2016, and that experience symbolized everything he detests about being a famous person—and the litany of coercion and artifice that someone in his position experiences.

“I did go, but I didn’t go there to be like, ‘Yo, take me serious,’ ” he remembers. “I was taking the piss! I went there as my favorite Mortal Kombat character, Jax.”

He continues: “The Met Gala is not necessarily anything that I ever knew about or was about. But my [former] stylist…would say to me, ‘This is really good for you to do.’ And no matter how strong you are mentally, you can always be swayed to do certain things. Now, it’s not something I would go to. I’d rather be sitting at my house, doing something productive, than dressing up in really expensive clothes and being photographed on a red carpet.… To do the self-indulgent Look at me, I’m amazing thing on the red carpet, it’s not me.”

Here Zayn catches himself, probably realizing this might register as a diss of Gigi Hadid, the 23-year-old supermodel he’s been in an on-again, off-again relationship with for two years. The supermodel who very much seemed to enjoy dressing up in really expensive clothes and being photographed on the red carpet days earlier.

“I get it, and I understand that people gain enjoyment from it,” he says. I ask if he followed along with the coverage from his couch. “No, no,” he says, and pauses. “Gi stole the night, though. The stained glass on her dress. Everyone else just put a cross on.”

When I ask Zayn if he has any confidants in the industry, he shakes his head vigorously. “No,” he says. “I don’t ever want to cross wires with other people too much. I just want to see the world through my eyes.”

Zayn grew up with three sisters (“I was outnumbered,” he says) and is still surrounded by women, ensuring that there’s a high level of exasperated but fond maternal energy swirling at all times. Blood relatives and the Hadids—particularly Gigi’s mother, Yolanda, who seems to have taken on a Kris Jenner–ian role in his life—make up much of his inner circle today. (“We get on. She’s really fucking cool. She’s a Capricorn. She’s the same star sign as me.”) He recently parted ways with his high-profile manager. His best friend is a younger cousin.

“I’m not [in] the mix,” he says. “I’m outside the mix.”

This kind of stubborn non-participation, of course, is a reaction to the years Zayn spent being in a mix that was not to his liking. When he was a kid, growing up in the northern working-class city of Bradford, singing was just one part of an aimless but all-consuming creative impulse. He never thought he was much of a singer, until one day the choir leader at his performing-arts school praised his voice and suggested that he try out for Britain’s premier vocal-competition show. Zayn’s mom had to drag him from his bed at 4 A.M. to attend the audition, where he broke from the typical pop fare with a rendition of Mario’s “Let Me Love You.”

After his X Factor audition, there was an exchange (never aired) in which head judge Simon Cowell probed baby Zayn. “ ’You know, with all these online platforms, why haven’t you ever put out anything prior to this?’ ” Zayn remembers Cowell asking him. Zayn seemed the type, after all: a soft-spoken and artistically gifted teen who liked to sing alone in his bedroom and tinkered with rudimentary song-recording equipment. “I didn’t necessarily think my stuff would be seen amongst the millions of people who put their stuff online. So I went with X Factor at that age,” he says now. Like any fickle teenager, Zayn “just did it for fun, to see what would happen.”

The day that Zayn auditioned, he was among many aspiring solo artists rejected by the judges. But five of the young singers were cobbled together as a boy band in a later segment. Thus was born One Direction and a rabid fandom that British people love to compare to Beatlemania. A craze so fierce and massive that it generated global synchronized flash mobs and fan-fiction authors who’ve reportedly scored six-figure book deals. In an instant, Zayn was thrust into a star-making boot camp, fast-tracked to an uncontrollable type of notoriety without being given the opportunity to consider alternatives.

It’s no secret that Zayn didn’t love One Direction’s sound or his bandmates. “My vision didn’t necessarily always go with what was going on within the band,” he says. There was something so earnest, so wholesomely dweeby, about the whole thing. It wasn’t cool, and Zayn didn’t particularly enjoy being dragged around the world to look like an epic dork during the prime of his youth.

When he split off, in 2015, Zayn finally got to do all the things he hadn’t been able to in One Direction: dye his hair, grow his beard, sing about sex. But he was also introduced to a fresh army of puppeteers trying to guide him, and he felt disoriented, adrift. The only way to ground himself was to resist the pull of anyone’s expectations and answer only to Zayn. He’d spent five years taking direction and had become allergic to it.

There are plenty of clichéd expressions about how toxic and stifling freedom can be, and Zayn experienced many of them when he went solo. “I didn’t really, like, make any friends from the band. I just didn’t do it. It’s not something that I’m afraid to say. I definitely have issues trusting people,” he says. When he was living in Los Angeles, aimless, he fell in with a crowd of industry people: “Producers, musicians, tailors, stylists, managers. Them kind of things,” he says. “It got too crazy. I just got too much into the party scene. Just going out all the time. And I was too distracted.” So he left L.A. permanently and moved to New York earlier this year as a way to bring himself back down to earth.

Running a bit further, he recently bought a farm in rural Pennsylvania on the advice of Yolanda Hadid, who also has a farm there. The farm? “Cool.” The state of Pennsylvania? “Cool.” If you haven’t picked up on it for yourself yet, Zayn loves the word “cool”; he loves it so much that he uses it more than 43 times over the course of our conversation. And now that Zayn likes to go to his farm and visit the Hadids, he and Gigi even have a horse together, named Cool. He’s just getting things going on the farm, but already there are crops of cherries, tomatoes, and cucumbers. He likes to ride his ATVs. Sometimes he and Gigi will go at the same time, and she’ll ride a horse, like Cool, while he watches.

Zayn has a habit of speaking in a conditioned state of detachment, responding in friendly but anodyne one-liners. Still, even someone who willfully projects this kind of cool two-dimensionalism can get irked from being flattened all the time by those around him. I catch myself flattening him, even when he’s right in front of me. When I bring up the deceased Lil Peep, with whom he shared a manager, I say that it’s a shame they never met—they seem like kindred spirits who could have made a great song together, or at least bonded over tattoos.

Zayn begins to laugh. “I’m not just going to be friends [with people] because we’ve both got tattoos. Loads of people come up to me and they’re like, ‘Yo, I got tattoos, you got tattoos. Let’s be friends.’ And I’m like… ‘We’re not just going to be friends because we’ve both got tattoos.’

“There’s a bit more depth to me than that,” he says, admonishing me.

One topic that will draw out this aforementioned depth is, unexpectedly, America. Despite the fact that he is living in a country under a leader that is exceptionally hostile to immigrants, the fantasy of America as a come-one, come-all melting pot is alive and well in Zayn’s mind. He says he’d vote for Oprah if she ran for office because he likes her “ideologies about the world” and she’s a “badass businesswoman.”

“The UK is like, Fuck you, you’re successful. That’s not a nice attitude to have,” he says. “You come to America, you’re a bit shocked at first: Are these people being genuine? Are they really interested in me? Do they want to have a conversation? But they do! And that’s a really nice thing. And I feel like it’s misrepresented across the globe. For the kind of country it is, because everybody supports, no matter what color, what gender, what sexuality, what class—none of that matters here. People genuinely want to know you for who you are. And that’s how America should be represented across the world.”

Maybe you should run for office, I say.

“Maybe. It’d be cool. I feel like it’s a beautiful place. [Because of the current political climate,] people are expressing how they really feel about where they come from and their heritage and their backgrounds. They’re all mixed. To be American, you are mixed.

“So that’s how I feel about it—it’s a beautiful place, and it’s a beautiful time to be alive.”

Another unlikely topic that will break Zayn out of his default conversational mode and get him talking in jolting, paragraphs-long monologues: the paparazzi. The paparazzi who have been trailing him for years and, recently, every time he sets foot near Gigi’s NoHo apartment, feeding the endless tabloid speculation about the state of their relationship. The paps used to piss Zayn off, until he realized their utility.

“That’s my promo,” he says. “I come outside, they take photos.” He gets to quietly remind people that he exists—and gets photographed looking like the second coming of Johnny Depp, leaving the apartment of one of the most gorgeous women in the world—without doing a thing. “They stay outside and do all the work!” he says. “You can get pissed off about it and be like, ‘Yo, this is a hindrance on my life.’ Or you can use it for your own benefit and be like, ‘Well, if they’re going to take the photos, then let them.’ You’ve gotta earn your dollar, and I’ve gotta earn mine.”

Which is to say that just because Zayn loathes the cornball industry churn doesn’t mean he needs to surrender his relevance. Zayn represents an era in which underground cool and mass-market, Calabasian-style popularity have collapsed into one another. He operates on a plane where celebrity is predicated chiefly on relevance and intrigue, and Zayn—with his equally illustrious girlfriend, his brooding glare, and his following of millions—has about as much relevance and intrigue as anybody. He is both a casualty and a beneficiary of this uniquely modern form of celebrity. In running from his stardom, he’s only fueling it.

I suppose now is the time to dispense with the rest of the intel I gleaned from Zayn about his relationship with Gigi Hadid, which was a less sensitive subject than I had anticipated. The two met at the end of 2015 at a party—which “pah-y,” Zayn will not disclose, but suffice it to say it was a “cool pah-y”—and just days later, Zayn learned she’d broken up with Joe Jonas. He reached out to her and asked her to dinner at the Bowery Hotel. And thus was born a couple that will go down in history as one of the most iconic and Zeitgeisty pairings of all time, a couple whose images I will show my grandchildren to prove that the world was better in my day. All of the gossip about their relationship being an opportunistic setup by their respective management is bullshit, Zayn says: “If a relationship is for your career, you can fucking walk out the door. No way. See you later.”

Despite the dramatic announcement of their split a couple of months ago, Zayn and Gigi are very much still close, as evidenced by myriad photos of him leaving her apartment or kissing her on the street. Zayn speaks about Gigi in a purely misty-eyed, worshipful tone that telegraphs he may be atoning for something. “I’m really thankful that I met her,” he says. He uses the term “we” in the present tense quite a bit: “We go to the farm.” “We have horses.” The time he actually rode a horse with Gigi, he says, “I looked like a complete idiot and she looked like a complete professional.… We’re still really good friends, and we’re still in contact,” he says. “No bad blood.” He laughs. “…Taylor Swift.

“We’re adults. We don’t need to put a label on it, make it something for people’s expectations.” To hear Zayn tell it, Gigi is the hyper-organized, clear-headed, and positive counterweight to his disposition, which can dip into a vacant or negative state. She helped him reset his attitude when he was releasing his first solo album, partying too hard. “I had a very negative outlook on things. That might have been adolescence or testosterone or whatever the fuck was running through my body at the time,” he says. “She’s helped me to look at things from a positive angle.”

As Zayn heads into his new album cycle, Gigi has been a font of support and organizational heft. He says she’s especially good with dates, which I mishear as “good with debts.”

She’s good with debts? You’re in debt?

“No, no. Dates. She doesn’t handle my finances yet,” he says. “We’ll get to that eventually.”

When Zayn Malik went solo, he dropped his last name. The mononymic “Zayn” took on a potency and directness that enabled him to break free from the chains of boy-band drudgery and lameness. Zayn: It’s a single syllable that conjures a vaporous sexuality and a moodiness that blurs the line between contemplative and blank. You can imagine the black-and-white commercial for L’Eau de Zayn.

In the years since he dropped his last name, the word “Zayn” has also become, to insiders, an equally potent verb. To “Zayn” means to be within someone’s reach one moment and then completely disappear the next without any explanation. Poof! To be “Zayned” is to witness a French exit so aggressive that it almost has a supernatural quality. I know this because it happened to me.

We emerged from the ship’s galley, and as I prepared to launch into more conversation, he asked Carolina where he could find the toilets. She pointed him toward a porta-potty on dry land, and Taryn wordlessly followed behind him, obviously accustomed to this ritual. Before I could get my bearings, he was zipping off into the parking lot adjacent to the tanker, no doubt scurrying home to his fortress of solitude and cigarette smoke in SoHo. I’d been Zayned.

We were supposed to hang out the following week, and I patiently waited for him to reach out. But I knew that he never would. And much as I’d like to be the exception to the Laws of Zayn’s Nature, I get it. Who among us has never fantasized about blowing off pesky professional obligations we deem useless? Zayn—driven by a spirit that is part self-destruction, part self-preservation, part youthful punk contrarianism—actually has the balls to live that fantasy. It’s self-absorbed, immature, and unprofessional. I’d be offended if I didn’t think it was so fucking cool.

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