Kendall Jenner Gets Candid About Her Career, Her Controversies, and Her Private Life

Kendall Jenner stables her horses at an unpretentious show barn called Huntover. It sits in an achingly romantic little spot tucked away in the gated community of Bell Canyon, California, about five miles from where she grew up in Calabasas. Huntover is owned by a genial, middle-aged gay man, Mark Bone, whom Kendall has known since she was thirteen, when she used to ride and train with him at a bigger facility not far from here.

“This is my little baaarn!” shouts Kendall, looking impossibly cool in skintight black riding breeches as she strides through a dramatic, Mission-style archway toward where Mark and I are standing, just outside her two stalls. Her horses, Belle and Dylan—both European warmblood mares trained as jumpers—sway their heads and whinny at the sound of their owner’s voice. Kendall feeds them treats from the palm of her hand and zips into a pair of black leather half chaps as she and Mark chitchat about horse people, including Bella and Gigi Hadid, who are also accomplished riders.

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“Where are you off to this time?” he soon asks, drolly teasing the highest-paid model in the world. “New York,” she says. “It’s Fashion . . . Month.” She rolls her eyes. “But I’m only doing a week.” This is one of the reasons Kendall has been able to start seriously riding again: After a few years of nonstop work, she has pulled back a bit from the grind of being at the top of the modeling world.

It’s a warm February morning, and the fog is just burning off. Kendall is here to ride Dyl, as she calls her, a horse she’s had for only two weeks. As Kendall makes her way over to the mounting block, Dyl is spooked by a couple of dogs sitting under a tree. “Oh, you’re afraid of the dogs,” coos Kendall. The relationship between rider and horse is a very particular thing—there is chemistry and courtship involved, a period of getting used to each other’s idiosyncrasies. Horse people have an expression about getting a new one: buying a friend. For someone who suffered from severe acne as a kid and had trouble making friends, Kendall’s connection to such sensitive creatures was not just formative; it was crucial. “I’m still learning her,” says Kendall. “It’s gonna take a couple months. It’s like with any person: You fall in love and then you feel each other out.” What do you know so far? “She’s a really good girl. She listens. She’s smart.”

Kendall heads into the ring and takes Dyl through some easy paces. She got her first pony when she was ten, and as a young teenager she helped out a woman who owned several horses. “I rode with this lady from 8:00 a.m. to 8:00 p.m., rode all her horses for her every day.” And then in ninth grade Kendall came out of her shell: She got a boyfriend and became a cheerleader. When she started modeling, not long after that, the riding stopped altogether. “Worst thing I ever did,” she says.

Belle came along about a year ago, right around the time that Kendall was feeling burned-out. She hadn’t had a real break in three and a half years and was suffering from debilitating anxiety and mysterious, intense neck pain. She began to dread getting on planes. “I made it a point at the beginning of 2017 to consciously slow down, take more time for myself, be more selective and not just do whatever my agents tell me to do.” All of which brought her back to the barn. “I did this my whole life—it was my life. I didn’t care for anything else, I didn’t care about boys. This is what makes me really happy.” She has since realized that she wants to go to shows—to jump again. “That’s why I got Dyl.” (It’s also why she’s committed herself to Transcendental Meditation. “I had a lot of people in the industry say to me, ‘I know you have a busy schedule—what do you do to stay calm, cool, and collected?’ I was like, ‘Um, nothing?’ And then one day, when I was having a freak-out—I was having multiple freak-outs—I was like, OK, I’m going to try this. So I found this lady, she’s awesome, she taught me TM, and I love it.”)

A few minutes later, Mark is at the center of the ring as Kendall canters in loops around him. She rides up to where I am standing at the fence. “We’re trying to think of an alias for me for when I go to shows, because I want to be under the radar,” she says.

“What’s your middle name?” I ask.

“Nicole,” says Kendall. “What about Nicole Dylan?”

“That actually kind of works,” Mark says.

I throw out the idea of using initials, like the writer A. M. Homes, so that when she registers they won’t know if she is a man or a woman.

“Oooh,” says Kendall. “I could be a boy.”

Kendall Jenner—a tomboy who collects vintage cars, prefers sneaks and jeans and a hoodie, and rolls with a squad of mostly guys—is not gay. Indeed, she is dating Blake Griffin, the Detroit Pistons power forward. She refuses to confirm this fact, but one of the reasons we can be fairly certain is that the day after Valentine’s Day she calls me from Michigan, and when I ask why she’s there she says coyly, “I’m visiting a friend.” When I ask point-blank if she has a boyfriend, she says, “I like my private life.” Pause. “Yeah . . . no. I’m happy. He’s very nice. I have someone being very nice to me.”

We are now in her Range Rover heading back to Beverly Hills for lunch. Why, I wonder, does the internet seem to think you’re gay? She laughs. “I think it’s because I’m not like all my other sisters, who are like, ‘Here’s me and my boyfriend!’ So it was a thing for a minute because no one ever saw me with a guy. I would always go that extra mile to be low-key with guys, sneaking around all the time. You don’t want to, like, look crazy.”

She pulls onto the freeway, and within seconds we’re going 90 mph. Kendall goes on: “I don’t think I have a bisexual or gay bone in my body, but I don’t know! Who knows?! I’m all down for experience—not against it whatsoever—but I’ve never been there before.” She ponders it for a moment. “Also, I know I have kind of a . . . male energy? But I don’t want to say that wrong, because I’m not transgender or anything. But I have a tough energy. I move differently. But to answer your question: I’m not gay. I have literally nothing to hide.” She lets out a mordant chuckle. “I would never hide something like that.”

She realizes that it’s only 11:00 a.m.—too early for lunch—so she gets off the freeway and heads toward Kardashistan: Hidden Hills, where she grew up and where her mother still lives and where Kylie and Kimye also now have homes. The Kardashian/Jenners may have started out as just another option on the reality-entertainment on-demand menu, but have since penetrated the culture so completely that you can hate on them, but good luck trying to ignore them. (“It’s almost, like, trendy to hate on my family,” she says. “It’s not so much that people actually believe that we suck, but it became a thing: If you hate on us, it’s cool or something.”)

We stop at the security booth at the entrance to the gated community, the driver’s-side window glides down, and Ken­dall says to the guard, perhaps for the millionth time, Hi, Kendall, going to my mom’s. A little less than two years ago, when I had dinner with Kendall at her mother’s house for a piece for this magazine, Kris Jenner cooked an elaborate feast for us and mostly left us alone in the dining room to talk. Later, though, she joined in for a bit, and when Kendall took a phone call, Kris and I went outside to tour the pool area. What a lovely person, I said. “My little human?” said Kris. “She’s a good girl. She has a good heart. She is definitely getting the most out of every day. Her life with her friends makes me smile, because in high school she had a few friends, but then she was homeschooled because we were filming Keeping Up. . . . It was just she and her sisters. So when she started modeling, she made all these great new friends, and I think it’s so cool that she has this wonderful life now.”

It’s less than a week since Kendall’s younger sister, Kylie, gave birth to her Super Secret Baby. (The ten children in the family now have thirteen children among them.) Kylie all but made her family sign nondisclosure agreements. When I ask Kendall about it, she first expresses exasperated relief that she’s finally allowed to talk about it. “It’s not that it’s more exciting than any other births in the family—it’s different exciting, because she’s my baby sister who I grew up with. We all grew up in twos: Kourtney and Kim grew up together; Rob and Khloé; Brandon and Brody; Burton and Casey, and then Kylie and I. So to see my best friend growing up have a baby? It’s already made us even closer.”

Kendall’s friends all talk about how maternal she is. Her self-described best friend, Taco Bennett, a 23-year-old DJ and member of the hip-hop collective Odd Future, says, “She’s like my second mom—she’s my club mom. Whenever I get drunk she takes care of me.” Says Kendall: “My friends make fun of me and call me Mama Ken because I literally take control of every situation. I guess I’m a control freak. Do you know how many times I’ve taken care of my drunk friends?”

Do you want to have kids? “I am ready to wait,” she says. “I want to have kids, but at, like, 28 or 29.” She also might want to get herself situated first. When I first met Kendall two years ago, I picked her up at her relatively new condo in Westwood, which was being packed up because she was selling it and moving into a house in the Hollywood Hills. Now, as we are driving around, she announces, “I bought a new house.” Another one? “Yes—I had so many problems with my last one. I got robbed. I had stalkers that literally broke in while I was home. It happened one too many times, and I just felt trapped.”

Her new house is, natch, in a gated community, way up in the hills off Mulholland. “It has a yard! And a big pool! It’s a whole . . . situation. I can go on walks. I can get a dog—and I can take the dog for a walk.” Just then we pull up and stop in front of her old house. “OK, so this was where they first started filming Keeping Up . . . but now it’s a completely different house because they tore it down, but the yard still looks the same, and they kept the front driveway, and . . . oh, my God! They kept our dollhouse! That was our little dollhouse!” And indeed, under a stand of trees in the corner of the enormous front yard is an elaborate little structure, kind of like a tree house relocated to the ground.

The gestalt of the Kardashian enterprise—the thing that makes it somehow feel universal—may very well be the simple idea of girls playing house. And right here, sitting just 50 feet away, is something like the Kardashians’ Mount Vernon, but in miniature. What did you girls do in there? I ask. “Go inside and play and stuff,” Kendall says, still wistfully on the verge of tears. “It’s crazy.” We sit there for a minute, and then Kendall says, “But they remodeled it,” and she steps on the gas and roars away.

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We finally make our way to the Beverly Hills Hotel, where Kendall avoids the porte cochere (and therefore the lobby) and heads down a ramp into a private underground garage where, as it happens, her latest purchase is parked: a purple, mint-condition 1960 Cadillac Eldorado Biarritz. Two years ago, she drove me around Los Angeles in her 1956 robin’s-egg blue Corvette convertible. I remind her that she described it as “not the most discreet form of transportation,” and she lets out a honking laugh and says, “This one’s even worse—it’s flashier, and it’s a boat.”

We head upstairs to the Polo Lounge and are seated at an enormous corner booth, and within minutes are approached by an oddly appealing young French couple on their honeymoon, hoping for a photograph. “She’s a huge fan,” says the man. “Oh, nice,” says Kendall. “Do you want to sit down?” It takes me a minute to realize that it’s simply less awkward in a busy restaurant for the stranger to sit for the photo than for the star to stand up. When they leave, Kendall says, “They were both, like, so pretty—both, like, tan, with spooky blue eyes.” I am struck by not only how polite she is, but how graceful. She seems to be effortlessly in tune with how people in different situations want to—and should—be treated.

Virgil Abloh, the Off-White designer, says that Kendall is his muse not because of her looks but because of her personality. “She exemplifies exactly what inspired me to design women’s clothes: She’s independent, strong, self-assured. It comes from a place of self- confidence, but with no air of arrogance, which is rare.” He thinks Kendall transcends fashion: “In 30 years, I wouldn’t be surprised if people have forgotten that she was one of the top models of the time and know her for something else.”

Kendall met Taco Bennett on Twitter seven years ago. “She’s cool as fuck!” says Bennett, who describes Kendall as a “lone wolf”—someone who “hides in plain sight better than anyone.”

Other than going that extra mile to avoid the prying eyes of the paparazzi, Kendall does not strain against being one of the most famous and beautiful women in the world. Indeed, she is appalled by some of the behavior she sees in the rarefied worlds she now travels through. “I have friends who have gotten sucked up in something that is so not real, and that is what I never want to do. My whole goal in life is to stay as humble and grounded as I can be, doing things that I love.”

I’ll be honest: I did not expect to be having conversations with Kendall Jenner about net neutrality or water shortages in Africa, but those things come up. When I ask her if she does any charity work, she says, “My mom always taught me—and I think there’s something in the Bible about this—when you do good works for others, you’re not supposed to talk about it.” She allows that she is involved with a nonprofit that helps provide clean water to people who need it most, and she regularly visits with and brings gifts to kids at Children’s Hospital Los Angeles. At one point I ask, When people think of you, what would you like them to think of—what do you stand for? “That’s a good question,” she says, and ponders it for a moment. “I’m only 22. I am still trying to find my path—in life, not work-wise.”

We talk a bit about the year or so since the last election. “It’s very unmotivating,” she says. “There are things happening that are just so . . . horrible . . . that it makes you not want to participate in anything. I’ve had days lately where I just want to sit in my bed and do nothing. It makes you scared to go out. It’s a complete nightmare. And I wish I had the power to fix it all.” I bring up the endless stream of news about sexual harassment and assault, most recently in the fashion world. “Luckily, I haven’t been put into a situation like that ever in my life,” she says. “I’ve heard about it for so long, I get it. I can try and understand it.

“But that being said, I think that it’s so powerful that, in a time that’s so . . . shitty, for lack of a better word . . . it’s just really cool and empowering to see a bunch of women come together and say we’re not going to stand for this—we’re not taking it lightly; we are going full force. That’s what I find so inspiring.”

But 2017 was a difficult year for Kendall in other, more personal ways as well. Every time she turned around, it seemed, she was accused of being clueless and tone-deaf in one cultural appropriation controversy after another: being photographed, as a non-Indian, for the cover of a tenth-anniversary issue of Vogue India, for example, but most notably, appearing in a now-notorious Pepsi ad that was taken off the air in 24 hours after a howl of outrage rang out across the land. A multicultural misfire, it depicted a faux protest rally, complete with cops and barricades, with Kendall cast as a model who walks out of her photo shoot to see what all the fuss is about, joins the rally, and crosses the barricades to hand a white cop a Pepsi—and then high-fives her new protest friends.

“Obviously, my intention was not to hurt anyone,” she says. “Honestly, I just hid out. It hurt me that I hurt other people.” She thinks for a minute. “I’ve been yelled at before, stepped in controversy before, but nothing to that extent. You can never really prepare for something like that.”

I ask her if—as someone with so many close black friends and family members—anyone talked to her about it. “No,” she says. “Nobody came to me to explain it to where I was like, Oh, I get it. But I’m not an idiot. I can see it for myself.” One of the more fascinating things about the Kardashians is that they seem so comfortably integrated as a family. In a country where, studies show, 90 percent of white people have no close black friends, I think that makes them good role models in one respect. When I run this notion by Kendall, she says, simply, “But that’s how I’ve grown up.” She pauses for a moment. “I didn’t think of the ad as controversial for exactly this reason. When it was physically happening—the high five? Isn’t that what everyone was freaking out over?—I just didn’t think of it like that.”

One of the big lessons she took away from the whole complicated rigmarole is to be more involved in every single thing she does. “I was always really nervous on any job,” Kendall says. “I am a huge people pleaser, and that is what my job has always been: You come to set and you do what you’re told. I don’t think of myself as anything special most days—I am just a normal-ass kid who likes to hang out with her friends and likes pizza. My family, my agent, my friends all make fun of me for it: Girl, you need to give yourself some credit. But that’s what I took out of it: I need to be more present and pay more attention.”

As our lunch comes to an end, I realize that Kendall is that rare person whose cool comes not just from her ease with the vernacular of hip-hop and fashion or her not-trying-too-hard style, but also because of her utterly unself-conscious earnestness and genuine interest in others. She’s emotional and vulnerable and open and easy to talk to. She isn’t judgmental or bitchy or glib. There’s no, like, whatever. I tell her about my first impression from two years ago: that she’d clearly been spending a lot of time around middle-aged gay men and overtraveled hair and makeup artists on photo shoots and had picked up their faux-jaded, world-weary lingo. To which she slyly replies: “Or you guys are picking it up from us.” Touché.

For someone so young, Kendall has the mind-set of someone much older. “At the end of our life,” she says, “you’re not going to care that you worked every day and you made this much money. You’re going to care about the relationships that you’ve built and the bonds that you have and the love that you’ve created. That’s what you’re going to care about. That’s my whole thing: what you leave behind.”

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