Meet the Prom Queen of Instagram

The Prom Queen of Instagram
High-school popularity can now exist well outside of high school — particularly if you are a certain kind of
teenage girl.
Photographs by Chuck Grant

It isn’t possible, objectively speaking, to declare one person the most popular teenager in New York City, but if you were making a list, there would be worse places to start than with Lilli Hymowitz. She is 16, the third of three sisters, and the owner of 7,989 followers on Instagram (at press time), where she presents her life as a perpetual party, much of which takes place by a pool. I first heard about her from a friend’s 15-year-old brother, who had been in the same room as Hymowitz before but was confident she had no idea who he was. This was a great disappointment to him. “Everyone wants to know about her,” he said. “She’s like a celebrity.” He knew whom she was dating, where her five tattoos were located, and when she had patched things up with her best friend after nine months of not speaking. He said that “Lilli’s Dark Circus,” her 16th-birthday party at Le Bain, had been the “party of the year.” Jason Derulo performed, and Hymowitz wore a low-cut black dress that made room for a necklace in the shape of red lips smoking a cigarette. “She’s rich and she’s pretty and she does whatever she wants,” he explained, before adding that her notoriety was of a particularly modern variety. “I guess you could say I know a lot about her from Instagram. I don’t really know her.”

By the standards of real celebrity, Hymowitz’s following isn’t especially impressive, but for an anonymous teenager lacking famous parents or, by her own admission, a particular skill — “I can’t, like, sing” — she is unusually popular online: not quite Instagram famous, but known well beyond the walls of any one school or the connections of any particular circle of real-life friends. For the aspirational caste that makes up much of the city’s teenage (and adult) population, Hymowitz represents, as one of them put it, an “Insta-ideal.”

She posts photos of herself next to DJs at clubs, wearing an angel outfit for Halloween, and topless in bed covered by strategically placed sheets, along with a smattering of horses and inspirational quotes and pictures of her baby half-brother. Were it cool to use hashtags, which she says it is not, many of her photos could be tagged #squad, to identify the rotating circle of friends in her orbit — attractive, stylish, posing in clubs and next to wineglasses and in the mirror, typically with looks of bemused detachment.

Her following, which is many times larger than the average high schooler’s, is a combination of random teens, the horse community, men in the Middle East, mothers in the Midwest, some bots, and people whose primary interest is finding out if she can help them hang out with Jaden Smith, whom she met through Tumblr. “I got a lot of followers when we became friends with some people that have names out there,” Hymowitz says. A photo she posted of herself with Madison Beer, a 16-year-old singer, and Hailey Baldwin, Stephen Baldwin’s daughter, got 1,836 “likes.” In May, 2,182 people liked a photo announcing that Hymowitz had gotten hair extensions.

A certain amount of Hymowitz’s appeal has to do with her extreme economic privilege — her father, a money manager, recently made the tabloids after trying to build a bowling alley in his townhouse — and though she knows people at Hewitt, Calhoun, Brearley, Columbia, Riverdale, and Dwight, she doesn’t know many who go to public school. Fellow teens describe her as a real-life Serena or Blair from Gossip Girl, which is meant as a compliment, or an Upper East Side Kardashian-Jenner, which is not. “Everyone I know including myself is sort of confused by her lifestyle,” a Manhattan private-school contemporary told me. “She has so many followers because people seem to be obsessed with seeing how rich young women live and seem to have flawless lives.”

Much of teenage life — the self-definition and posturing, the longing and experimentation — now happens online, such that the pursuit of friends and status and popularity no longer stops at the cafeteria door. Instagram and the like offer Hymowitz a scale of extracurricular notoriety that the popular girls of even ten years ago could never have comprehended. From a distance, that reality can seem disturbing; up close, it’s some combination of liberating and terrifying. “You can edit your life on Instagram,” Hymowitz says, before admitting, “I think people think I’m cooler than I am.”

In real life, Hymowitz is five-foot-one when she isn’t wearing heels, with dark hair that she is currently trying to lighten, in stages, so that within a couple of months she’ll be blonde. She is about to start 11th grade, which she thinks could be auspicious. “Eleven has been my number forever,” she says. “My bat mitzvah was on 11/11, and at 11:11:11 we had a countdown.” She divides her time between a townhouse (owned by her father) and an apartment (her photographer mother’s), both on the Upper East Side. Her favorite places in the city are the Great Lawn and “downtown.” She has a fake ID and no curfew. She thinks “big parties are the most intimate,” and that there are few feelings better than a shower in the morning after going out the night before. Asked to name her favorite subject in school, she offers the coolest response imaginable: “I hate school.”

My first one-on-one audience with Hymowitz took place late one summer afternoon, in Sagaponack, where her father has a home. Like any celebrity, Hymowitz is smaller than she appears onscreen, and I wandered aimlessly around the crushed-rock driveway until spotting her behind a wall of luxury SUVs. Online Hymowitz looks 25, but in person she presents much more like her age. She wore white sweatpants and a blue flannel shirt with DON’T WORRY BE YONCE stitched on the back. Her toenail polish was patchy. She had an Apple Watch on one wrist and three bracelets on the other.

Hymowitz used to spend all summer in the Hamptons, but lately she has preferred to stay in the city with her friends. “They’re not interested in just hanging in the backyard doing nothing,” her mother, Debby Hymowitz, said of her daughters. We had been watching Lilli compete in the Hampton Classic, a horse show, earlier that day. Lilli, who has been riding since she was 4, is a fixture on the riding circuit, traveling to competitions in Pennsylvania, Florida, and occasionally Europe, but her interest in horses has diminished along with her desire to spend all summer in a beach house with her parents. She had been training less, and in the jumper competition, she got no ribbon. “I tell her, ‘Just scale back, make time for other things,’ ” Debby said. “Life is a puzzle.”

Lilli ushered me to the pool, where she settled into a modern white deck chair, crossing her legs on the seat in a pose of serene confidence. It was as if she had been giving interviews all her life, even though she had only done so a few times before, for horse blogs. Debby said hello before heading off to SoulCycle, and Lilli’s father, Gregg, stopped by to warn “No drinking,” but otherwise Hymowitz handled this on her own. “When I meet people outside New York, they’re like, ‘You are not 16,’ ” she said. “I’m just like, ‘This is what 16 looks like in New York now.’ ”

Hymowitz was born in 1999, but she has, according to her 19-year-old sister, “been an adult since as long as I can remember.” She got her first cell phone at 7. At 13, she presented her parents with a PowerPoint explaining that she was done with Judaism and wanted to become a Buddhist. (She still had that 11/11 “faux mitzvah,” at which LMFAO performed.) In the past year, she has turned her body into a permanent reminder that no matter the struggles of the present, everything would be okay: a globe tattoo on her wrist, to remind her that she is only a speck in the universe; a pair of duck’s wings, just south of her armpit, to remind her that, in a fight, ducks flap their wings several times, then move on. She has already acquired and discarded a series of life mottoes, including “Everything happens for a reason,” “Never major in minor things,” and “Instagram is only the half of it,” which used to be the tagline on her profile until she replaced it this year with “Living lightly.”

When Hymowitz first joined Instagram, in middle school, her account was private, but by the time she started high school she had opened it to the public. She has posted thousands of photos, but fewer than 500 are extant because she began to realize that many of the things she used to care about didn’t fit with her current persona. “I deleted a bunch of the photos I didn’t like anymore,” she says. “Now I think I’m at a place where I don’t really change that much.” She used to dress more colorfully but now wears mostly black and prefers, as one of her friends put it, “swagged-out leather shit.” The oldest photo Hymowitz has not deleted, and thus the earliest moment she has deemed relevant to her current self-image, is of a marijuana-leaf bracelet, posted when she was 13.

City kids grow up fast, but Hymowitz says she grew up even faster because of what she refers to, lovingly, as “our modern family”: her mother and father, who divorced when she was 7; her older sisters, Jenna and Cloe, both at Duke; her father’s second wife, a former Knicks City Dancer, and their 6-month-old son, Luca; and her mother’s partner, Stacey Griffith, a popular SoulCycle instructor. Griffith is the only member of the family with more Instagram followers than Lilli. The gap narrows by the day.

“On Instagram, my mom writes a caption that’s a whole long story with a start, middle, and an end,” Lilli told me one day at her mother’s apartment. “We’re like, ‘Mom, make a blog!’ ”

“I speak in sentences,” Debby said. “I’m a grown-up. That’s how I talk, so that’s how I write, so that’s how I Instagram.”

Hymowitz has a close relationship with both her parents: Each member of the family has an H tattoo, but when Lilli got hers, last year, she wanted to be different, so she got an h. All the Hymowitz children went to Riverdale. “Everyone knew who she was, even if you weren’t in the grade,” one Riverdale student told me, requesting anonymity because he hoped, one day, to hang out with Lilli. But Hymowitz would often socialize with her sister’s friends, who were two grades older. On a recent Thursday night, she occupied a table at Bagatelle, in the Meatpacking District, with eight freshmen in college.

“It’s 11:11, touch my tattoo,” she said, asking them to rub the cursive ELEVEN she had inked on the back of her neck. She turned to her friend Sammy Nussdorf and told him to pose for the camera.

“Are you out of your mind?” Nussdorf said, looking at the photos. “These are horrible.”

“What are you talking about? That’s the best photo you’ve ever been a part of,” Hymowitz said. “Honestly, that’s your new prof” (as in “profile picture”).

While two of her friends sloppily made out and several others stepped outside for a smoke, Hymowitz sat in her seat posting a photo to Instagram. Every so often, she checked in: 77 likes in 12 minutes. “I obviously think it’s cool that I have a follower base, but my goal isn’t to ‘get to the K,’ ” she said, referring to the abbreviation Instagram bestows on anyone who passes the 10,000-follower mark. She used to care about how many people she followed, figuring that the lower the number, the more exclusive her club would appear, but has since loosened her standards while also pointing out that of the 139 people she follows, only a dozen or so — Big Sean, Drake — don’t follow her back.

Hymowitz’s online notoriety has benefits that could entice a kid but might disturb a parent: Promoters invite her to clubs in the comments of her photos — after Bagatelle, she and her friends went to the grand opening of a club one of them had heard would have televisions playing porn and tables reserved for “snorting, um, baby powder” — and strangers send their phone numbers in direct messages. When a photo of Lilli sipping a Starbucks drink in a hot tub elicited a number of comments from strangers, Cloe, who keeps her own account private, posted a comment asking her little sister, “can u get off public ur comments are weird.” Once, in Central Park, Hymowitz says she spotted a teenage girl taking a surreptitious photo of her from behind a pair of raised knees. When Hymowitz walked by, she heard the girl whisper, “That was Lilli.”

By my count, Hymowitz refers to at least six people as her best friend, but the primary claimant to the title is Camille Curtis, an 11th-grader at Hewitt who shares Hymowitz’s affinity for black clothes, chokers, and hip-hop. They have known each other, as Hymowitz put it, for “three and a half years, with a nine-month break,” which neither of them was eager to detail, save for saying it was Curtis’s fault.

“ ’Cause she’s a bitch is why, right?” Hymowitz said, looking at Curtis.

“I didn’t have any intention of ever being friends again,” Curtis said. “But then I came back.”

Their breakup had been widely noted — from Tumblr: “You and camille not being friends anymore feels like a celebrity couple breaking up” — and they announced their reconciliation this summer with a photo of Curtis holding up a gold F and Hymowitz a matching U. Since then, the pair have appeared on Hymowitz’s Instagram showing off their tattoos in a bathroom mirror, posing in front of a bodega flower display, and rolling around on the handle-free scooters popular with Justin Bieber and professional football players, lip-syncing to a rap song: “The shit I do at 17 supersedes / What you gon’ do by 30.”

Several weeks after their reconciliation, Hymowitz and Curtis were at Debby’s apartment, in the East 80s, which is decorated with poster-size photographs of women in various states of undress from Debby’s gallery exhibition “Sexual Evolution.” Lilli’s room is generally neat and uncluttered by the typical destruction of teenage life, though her bed sometimes remains unmade and she warns visitors about the smells from the four dogs she and her sisters persuaded her mother to buy. “They all became her dogs and none of them cared about me,” Lilli complained.

Wearing matching black dresses, Hymowitz and Curtis settled into Lilli’s bedroom and logged onto YouNow, a service that allows users to stream live video of themselves to viewers, who can ask them questions in real time through a chat interface. (The site claims 100,000 broadcasts a day; 70 percent of its users are under 25.)

Much of what would have previously been reserved for a diary Hymowitz and other teens now regularly share on YouNow and Tumblr and Among the things anyone with an internet connection can learn about Hymowitz — I watched the YouNow stream online before she and I had ever met — is that she had been a vegetarian for five years but started missing chicken fingers and gave it up. She would name a female child Wynter and a male child Dex. Her favorite emoji is “the cute sad one.” Most of the information is benign, but it is also possible to find answers on various sites about the first time she “hued” — as in hooked up; whether she has ever had plastic surgery (no); and whether she knew that one of her friends had hued with a guy she liked. (“Clearly then they deserve each other.”) The question-and-answer sessions could be validating — “love u even if u don’t know me” — but leaned critical: “you were so nice when we were little and now we dont even talk.”

Hymowitz regularly gets requests to do more livestreams, to which she and Curtis had acquiesced. “Guys, you should probably ask us questions,” Hymowitz said as she sorted out some technical difficulties. “This is embarrassing.” Panda, Lilli’s gray-and-white Aussiedoodle, wandered in and out of view. Curtis has less than half as many online followers as Lilli and urged her to announce the stream on Instagram, which led to a discussion of how to deal with the onslaught of smartphone alerts from the app.

“I only get notifications when people I follow like my shit,” Hymowitz said.

“Really, you can do that?” Curtis asked.

“What do you think every famous person does?”

“If you’re famous I don’t think you would be like, ‘Ooh, Drake liked my photo.’ ”

“Oh, I for sure would.”

The number of viewers began to rise, and the girls started taking questions about where they liked to shop — Intermix, Rag & Bone — and Hymowitz’s favorite piece of jewelry: She displayed a gold ring on her finger by flipping her audience the bird. Most of the queries were directed at Hymowitz, who took the lead:

How do you get a tattoo in New York if you have to be 18?

Fake IDs, or just go to a bad place.

What’s the last club you went to and was it fun?

Sono, and no.

What’s your GPA?

Don’t know.

What do you want to do as a career?

Just livestream all day.

The livestream questions quickly moved to less comfortable areas, such as whether Hymowitz was currently dating her on-again-off-again boyfriend, with whom she told me she had gotten into several of the kinds of fights she says plague young relationships: “Why didn’t you tag me in that photo of us? Why didn’t you like my photo? Why did you like this guy’s photo?”

“I was worried someone was gonna ask and I was gonna have to answer on the spot,” Hymowitz said.

“Well, it’s not really on the spot, because you could just easily not answer it,” Curtis pointed out.

Hymowitz paused. “No, we’re not dating,” she said. “Love him, but we’re like best friends for now. Shit changes. Life happens.” When someone asked about her favorite memory with him, she said, “Paris,” then picked up Panda and stroked his back while looking out the window. 

Just before Labor Day, Hymowitz and Curtis met a few friends for dinner at Cipriani Downtown in Soho. Even in 2015, there are limits to the power of localized teenage Instagram fame, and Hymowitz was able to get the host’s attention only after mentioning that her friend Jackson Lee, a freshman at NYU and Spike’s son, would be joining her. “Shout out Spike,” Hymowitz said.

“Did she tell you how she met me?” Lee asked as he sat down.

“Oh my God,” Hymowitz said. “This makes him feel really cool.”

“She used to go to Knicks games, and she stared at the back of my head for, like, years,” Lee said.

“Oh my God!” Hymowitz said, her voice escalating to a pitch typically reserved for uncool fathers.

“Then one day she just decided to message me on Facebook,” Lee said.

In addition to Curtis and Lee, Hymowitz was joined by Jeremy Quezada, a senior at Calhoun, who had seen Hymowitz’s Instagram before ever meeting her, and who requested that I include just one thing in this article: Cloe Hymowitz, Jeremy Quezada thinks you’re hot. Hymowitz rolled her eyes as a waiter dropped off a wine list. “Some Bellinis? Champagne?” he asked.

Hymowitz asked for a cappuccino — she started drinking coffee last year — and a $16 plate of French fries. She had just come from the salon, where she had gotten rid of her extensions and lightened her hair several shades. “He hates it,” she yelled at Quezada with flirtatious venom. “Why did none of you notice her eyelashes?” Curtis opened and closed her recently extended eyelashes. “You guys see her every day,” Hymowitz said. “You should have noticed.”

“They don’t get along with other girls very much,” Lee said of Hymowitz and Curtis.

“That’s not true!” Hymowitz said. “Girls don’t like us together.”

“They’re like a power couple,” Quezada said. “Like Jay Z and Beyoncé.” Hymowitz was Jay Z, he said, “because she calls the shots,” and Curtis was Beyoncé because “she’s there looking cute all the time.”

“None of us go to the same school or ever did, which is weird,” said Hymowitz. Even weirder is the fact that for the past year, Hymowitz hasn’t gone to any school. Near the beginning of her sophomore year, she dropped out of Riverdale to focus on horse riding, and she has been homeschooled by tutors ever since. (Cloe, now a freshman at Duke, had done the same.) “Some people think if you’re homeschooled your kid’s going to be alone, but because she was already so old and had friends, it wasn’t like she hadn’t learned how to socialize,” Debby says. Remarkably, Hymowitz’s Instagram following has only grown since leaving Riverdale. Attending high school, it seems, is no longer a requirement for being a popular high schooler.

Everyone at the table said their online profiles were, if not the best version of themselves, then certainly a particular one. Lee posts almost exclusively in black and white; Curtis regularly deletes her photos. Quezada, who plays basketball, largely posts himself in various states of dunking; he also spends the least time on Instagram — he posted just one video and five pictures all year, including a shot from the “Lilli’s Dark Circus”–watermarked photo booth — and everyone agreed that he has the most real-life friends.

Hymowitz asked her friends if they thought her Instagram captured her personality. “Definitely not,” Lee said. “Your Instagram is like, ‘She does cool stuff.’ It’s a lifestyle that people want to live.” Everyone agreed that Hymowitz was sweeter in person than the cool, even tough, persona she presented online.

The table also agreed that building a high-profile online presence was practical. “When I decide what I wanna do in general with life, having followers could help,” said Hymowitz.

“If Lilli wanted to model, she most likely could,” Curtis said.

“Definitely too short,” Hymowitz said.

“You could do commercials,” Curtis said.

“What would I model for?” Hymowitz said. “I could be a shoe model. My feet are the perfect size.”

When I asked Hymowitz if she saw herself, as others did, as a Kardashian-Jenner in training, and whether the ultimate goal might be a show called Hanging With the Hymowitzes, she paused for a very long time. “My parents would never let me,” she said. “My friends are gonna disagree with this. But I honestly don’t think I have enough drama in my life.”

They did disagree, but I could sense a tinge of regret from Hymowitz that her life didn’t wholly match the Kardashian-esque one she presented online. Like most teenagers, her reality involves a great deal of aborted plans, boredom, and sitting around wondering if the future might hold something better, or at least something different.

“Guys, remember last night when we were all chilling and nobody was talking for a long time,” Curtis said as they finished up dinner.

“I was falling asleep,” Lee said, before nodding at Hymowitz. “She gets mad if you try to leave. So then it’s like 5 a.m. and if you leave, she gets pissed.”

“That’s not true,” Hymowitz said. “I just don’t like when people leave. It’s sad.”

Earlier this year, Hymowitz realized that she wasn’t very happy. “Lilli’s Dark Circus” had been a success — 731 likes for a photo with Jason Derulo — but she had been in the throes of a breakup and had not been on speaking terms with Curtis. “Everyone’s like, ‘There’s so many people in New York, if you don’t want to be around the same people, why don’t you just meet new friends?’ ” she said. “But you can’t just wander the streets and pick out new friends.” As she crested the halfway point of high school, she seemed stuck between being an aspiring adult and a romantic teen who still posts pictures of Drake and says that all she needs is a man who would treat her like he would. Instagram offered a concrete measure of her popularity, which could be reassuring but also, she now realized, paranoia-inducing. “How do you even know why someone is hanging out with you? Is it for them to tag you in their Instagram, or is it because they like you?” Hymowitz wondered.

Hymowitz wanted to do something drastic — leave New York maybe — but her father suggested she start by reading a book, The Power of Now: A Guide to Spiritual Enlightenment, by Eckhart Tolle. After finishing, she got the word NOW tattooed on the inside of her middle finger. She said the book had helped her realize that the events of seemingly great importance that dominate the life of a teenager weren’t, in the end, a very big deal. On Instagram, she started supplementing poolside shots with inspirational quotes. “He thinks that if it’s a true representation of you then it’s not that big of a deal,” Hymowitz said of what Tolle thinks of social media. “If you’re not, and you’re trying to be something for Facebook or Instagram, then it’s really poisonous.”

Hymowitz was sitting on the floor of her bedroom in her father’s townhouse wearing black boots, black leggings, and a black jacket. The room, which rarely appeared on her Instagram, could have been a 12-year-old’s: three teddy bears, a bookshelf filled with a glass-animal collection, an entire wall devoted to horse ribbons. As Panda ran around the room looking for attention, Hymowitz was scrolling through her Tumblr, picking out meaningful images to paste in a collage next to her bed. “I’ve been wanting to do it forever, but I just haven’t had the time,” she said.

Her high-school friends were back in school, but two of her college-aged friends, Nussdorf and Izzy Eide, had come to help. “That needs to be on my wall, right?” Hymowitz said, pointing to a photo of a sign that read I TOLD MY THERAPIST ABOUT YOU. The pictures she’d pulled as her favorites ranged from portraits of Rihanna to inspirational quotes. (“It’s only after losing everything that you’re free to do anything.”)

Eventually, Hymowitz picked out 90 images. But as the time came to put them up on the wall, her friends asked if she wanted to go out instead.

“Are you doing this all night?” Eide asked. Hymowitz had a horse show at 8:30 the next morning but didn’t need much convincing. “Oh yeah, alllll night,” she said. “No, I’m not. I can come.” She changed into a black top and white high-top Versace sneakers; a few hours later, from a club downtown, she’d post a photo of her sneakers surrounded by several dollar bills on the ground. As they got ready, she talked about a party she was planning at her mom’s apartment.

“I’m thinking like 40 people,” Hymowitz said.

“Do you even like 40 people?” Nussdorf said.

Hymowitz thought for a moment. “I’m not sure I know 40 people,” she said. “It would be ten people I actually like.”

*This article appears in the September 21, 2015 issue of New York Magazine.