Kylie Jenner is the first one to tell you: You don’t become the hottest thing on social media without knowing exactly what to filter.
The patio restaurant at the Sunset Marquis in West Hollywood is bright with California sunlight. This is where I’m meeting my lunch date, and right from the start, the restaurant manager—a dapper fellow named Lance—mistakes me for an “advance man.” It’s not unreasonable to assume that I would be sent by Kylie Jenner’s team to scout out the most suitable table and make sure everything will be to her liking. But it would be incorrect. No, I tell him, I’m actually the magazine writer she’s meeting. “So sorry,” says Lance. “It’s just—it’s Kylie Jenner. I figured there’d be an advance man.”
I have no experience as an advance man, but I pick a table tucked away in the back, where she seems least likely to be noticed. And going unnoticed is not easy for the 18-year-old. Beyond starring on Keeping Up With the Kardashians, the reality-TV soap opera now in its twelfth season, Jenner is something of a social-media savant: 63 million followers on Instagram, 16 million on Twitter, and a rabid following on Snapchat. Whether she’s featured on gossip sites that are reporting on her recent breakup with rapper Tyga, or on promoted posts about her wildly popular line of Lip Kits (if you’re not sure how wildly popular, consider that they sell out in minutes), or on her best-selling lifestyle app, Jenner’s face is just about everywhere. (A recent scandal erupted over those famous liquid lipsticks: Some boxes arrived empty after the goods were stolen from doorsteps. Now they come in nondescript packaging.)
Given her star wattage, it comes as something of a surprise when Jenner sidles up to my table all by herself, bereft of entourage, paparazzi, or adoring fans, her lone handler retreating to the shadows. She gives a pleasant hello and slides in next to me, saying, “You hungry? Let’s eat something!”
Most celebrity interviews play out by a certain set of unspoken rules. The writer’s job is to try to uncover the “real” person behind the famous name; the celebrity’s job is to promote her latest movie/album/product while seeming friendly and uncontroversial. But I’m not the only one trying to sleuth out the person beneath the Kylie persona. Recently, I tell her, I’ve noticed a new phrase trending on Twitter: #WhoIsKylieJenner? She laughs. The hashtag, she explains, stems from a recent Snapchat post where she’d alluded to a gulf between Kylie The Brand and Kylie The Actual Person. “I don’t even know who Kylie Jenner is,” she’d mused to her phone’s watchful eye in a self-reflective moment. It inspired the new hashtag and fevered responses on Twitter from both her most ardent fans (“Kylie is so perfect”; “Kylie is me”) and saltiest haters (“She is a black girl parody”; “She’s a girl who’s rich for doing absolutely nothing”).
Jenner leans forward, sips from a $7 bottle of water, and does her best to clarify. “People think that since we have a reality-TV show and I show so much of my life that they know who I am. But on Snapchat I show people what I think they want to see”—luxury cars, mansions, her family. “That’s not me. It’s a projected image. A brand. I’m not a different person. I just don’t show all of me.”
Fame and riches don’t erase a person’s natural sensitivity or make them so thick-skinned that they’re immune to criticism. “I usually don’t show my true personality to the world,” Jenner tells me, “because when you open yourself up so much, there’s more room for people to say things about you.” Craftily, sensibly, she seems to have created a separate persona: Kylie The Brand. When people attack KTB, as they often do online with surprising, sustained venom, Kylie The Actual Person knows they’re attacking something that is not who she really is.
Reasonably, then, she is coy about revealing Kylie The Actual Person to a reporter. When I ask what parts of her a person might discover if they were getting to know her in a more authentic way, she deflects with a smile. “See, this is where #WhoIsKylieJenner comes into play. I don’t really say who Kylie Jenner is, you know what I mean?”
And yet in the hour that follows, she slowly, graciously, gives me peeks behind the curtain, offering some tantalizing morsels about her real life and sharing a sense of what it’s like to be a teenager living in the eye of a media hurricane. So who is Kylie Jenner?
She’s someone who craves normalcy.
On one hand, Jenner says, she wouldn’t trade the life she has for anything. She’s grateful for a life of adventure and thrilled that she has such an enormous platform from which to pursue—with wild success—her dream of creating a cosmetics line. (Her dreams may not exactly be high-minded, but they’re honest, and coming from an 18-year-old, they’re possible to forgive; she’ll have the rest of her life to save the world.)
Maybe not today, maybe not tomorrow, but at some point, Jenner knows, the limelight will fade—or, more likely, she’ll simply walk away from it. “I know I don’t want to be famous forever,” she says. “There’s gonna be a time where I feel comfortable, I’m at a good place in my life, and I just stop.”
At that still distant, unknowable point in the future, Jenner wants to do “normal things,” like start a family. “I don’t necessarily have to date someone who’s famous,” she says.
She’s a crier.
It’s not that life gets Jenner down so low, or that she holds within her some terrible sorrow. Hers are more like happy, sentimental tears that often seem to strike without warning. Maybe it’s a close friend or family member she hasn’t seen in a long time—a meaningful hug will squeeze a couple tears out of her. Maybe it’s a sappy commercial. Once, Jenner says, she was watching Teen Mom, and when one of the teen moms gave birth, “the girl was so emotional, it just made me cry.” Does that mean kids one day? “Eventually,” she says. “Of course.”
She works her ass off.
Jenner is rich—was born rich, really—but don’t get it twisted: She wouldn’t have the mega-riches she has now without a relentless work ethic to match. “I’m always thinking about working,” she says of a trait her mother instilled in her. In the last year, Jenner has added a fashion line (Kendall + Kylie) and a nail-polish collection (for SinfulColors) to her portfolio. Of course, some of her “work” is also fun—presenting at music awards, attending the Metropolitan Museum of Art’s Costume Institute Gala—but downtime is a rare commodity. There’s always another photo shoot, another party to attend, another plane to catch, another product to endorse, another magazine interview with some middle-aged writer who wants to get to know “the real Kylie,” another video post to drop into the jaws of the ravenous social-media beast. And what would feel glamorous if it happened once a year, or even once a month, becomes work when it occurs daily.
But Jenner has a high motor and welcomes the constant grind. “Even if I did have the chance to hang around all day,” she says, “that’s not what I want to do.”
She retains an essential sweetness and sense of nostalgia.
When I ask Jenner about her first kiss, her level of engagement—already high—ratchets up to a new gear, and she dives into the story. His name: Matthew McGraw. The grade: fourth. “We were in the front yard of my best friend Zoe’s house, just me, Zoe, and Matt. He was one of the hot ones in fourth grade, and yeah, I definitely had a crush on him. Zoe was like, ‘Just do it!’ It was an innocent peck. Right on the lips. And it was funny and awkward, probably like every other first kiss.” For a moment, she’s lost in the memory of a time just before Keeping Up With the Kardashians hit the airwaves and everything in her life changed.
Years have passed, and though she and Matthew remained friends, they never dated. Where is Matthew now? “He’s in college,” she says, sounding a bit wistful. “You know, probably what I’d be doing.”
She seeks true happiness.
What is the endgame here? More fame, more fortune, more social-media followers? That is a tougher one for Jenner to answer. While she marvels at the power of social media—her obscenely abundant following, her corresponding ability to sell out a line of Lip Kits—she also feels that she needs to go hard now, since her moment in the spotlight could prove fleeting. “I don’t know how long all of this will last.”
Ultimately, because she is someone who grew up in the limelight and continues to bask in it, she views what makes people happy differently than those still striving for the success she somewhat carelessly achieved long ago. “I’m a special case,” she admits. “I can’t remember what it’s like not to be famous. So I’m able to appreciate what true happiness is all about. A new car, that’s not real happiness. That lasts a month. That’s short-term happiness.” Happiness, she explains, is “being with your friends.” She gives me a sober, serious look. “Right?”
She cherishes family above all else.
On a daily basis, Jenner suffers the slings and arrows of outrageous fortune, but she’s not alone. Her older sisters, her brother-in-law Kanye West, they’ve been there, too. “Honestly,” says Jenner, “if I didn’t have my family in my life, and I was going through all of this myself, I don’t know what I would do.”
Perhaps nothing in their tumultuous lives has been more precarious and incendiary than the announcement by Jenner’s father, Caitlyn Jenner, in 2015, that she identified as a woman and had decided to change her name to Caitlyn. But it wasn’t a shock to Kylie. “When we were younger, me and Kendall would run into [our dad] fully dressed in women’s clothes. It was a secret.”
One day, when Caitlyn felt her daughters were old enough to handle it and fully understand, she sat the whole family down and shared her plans. Kylie remembers how emotional her dad became, concerned that in pursuit of her true self she might hurt, damage, or embarrass her daughters. “I just told Caitlyn, ‘You should do what you want in your life.’ I’m just happy that she can live her life as herself now.”
Jenner swells with pride thinking about the ways her dad’s public transformation has played a role in transforming society. “A lot of young transgender people look up to [Caitlyn], and she’s doing a lot [to educate people] around the world. All she cares about is helping other people who are going through the same thing.” It’s easy to get the sense that whoever Jenner is, and whoever she might become, her family will always shower her with love and acceptance—the most generous of all gifts—with no strings attached.
Back at the Sunset Marquis, our conversation winds down, and I’m starting to realize I’m a crappy advance man—Jenner would have been well served to bring her own, maybe someone with better instincts. The table I’ve chosen, tucked away in the back of the restaurant, happens to also be positioned right next to the women’s restroom—a bungling, rookie mistake. For the past hour, a steady stream of women have passed by, and almost every one of them, from teenagers to older women, has done a quick double take at the least, and some have stopped and stared.
I ask Jenner if she’s ever seen The Truman Show, the funny, terrifying, and prescient Jim Carrey movie from 1998 about a guy who discovers that his entire life has been a reality show. She hasn’t; the movie hit theaters when she was nine months old. It strikes me that Jenner’s life has been a kind of bizarro Truman Show sequel—a woman whose entire life is a reality show, and she knows it. In the moments when TV cameras aren’t pointed at her, Snapchats, Instagram posts, and Vines fill the gaps, along with lenses aimed her way by fans and paparazzi. So which is the bigger mindfuck: to have the whole world watching you but be oblivious to it, like Truman, or to be fully aware, every second of every day, like Jenner?
As she gathers her things and prepares to head off, I brush a tiny spider off the table, and our conversation pivots. I ask Jenner how she feels about spiders—does she love them or hate them? In one strange, elongated moment, the tension between Kylie The Brand and Kylie The Actual Person becomes almost visible, as both seem to be wresting for control. At first, she gives the kind of response a publicity team might craft for her: She’s not scared of spiders. When she finds them in her house, she catches them and puts them outside. In fact, she makes a point of never killing insects. To me, this all seems to be full-force KTB, toeing an eco-friendly party line.
But when I push back a little—really? You actually catch the spiders? How, exactly? In a cup?—Kylie The Actual Person comes wading in. The truth is, KTAP says, she has occasionally tried to sweep spiders out of the house to avoid killing them. If they won’t go, she’ll resort to other measures. Recently she found a black widow out in the garage. Terrified that her family’s dogs might wander into its web—a legitimately dangerous prospect—she gathered some kitchen cleaners and sprayed the spider and its eggs until it had drowned in toxic foam (a fate, one imagines, she might also like to level upon her Twitter antagonists). Finally, she called for help to remove the spider’s corpse; a widow, even dead, might have poisoned her dog.
