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Harry Styles and Kendall Jenner's Relationship: A Look Back

Harry Styles and Kendall Jenner were romantically linked from 2013 to 2019

Keeping Up with the Kardashians star Kendall Jenner and Harry Styles were romantically linked multiple times from 2013 to 2019.

Although they never confirmed their relationship, the model and singer share quite a romantic history, including taking trips on Ellen DeGeneres ' yacht and going on ski vacations for New Year's. Jenner and Styles even enjoyed a memorable "meal" together when the former One Direction member filled in for James Corden as host of The Late Late Show in December 2019. During their appearance, the two looked like old pals while playing Corden's "Spill Your Guts or Fill Your Guts" game.

From casual nights out to sharing secrets on late-night TV, here's a look back at Harry Styles and Kendall Jenner 's relationship through the years.

Nov. 20, 2013: Harry Styles and Kendall Jenner have a date night in West Hollywood

In 2013, following his split from Taylor Swift earlier in the year, the pair shared dinner at Craig's restaurant in West Hollywood and were photographed leaving the restaurant in Styles' car. The meeting sparked rumors of romance that both parties were quick to deny. "They're just friends," a source told PEOPLE at the time, while Kendall assured everyone on Twitter that she was, indeed, single.

Flash forward to Dec. 1, 2014, when the pair hung with pal Cara Delevingne (pictured above) at the British Fashion Awards at the London Coliseum, again sparking rumors of a romance.

Jan. 1, 2014: Harry Styles and Kendall Jenner go skiing together

On New Year's Day in 2014, Styles and Jenner were spotted skiing and snowboarding in Mammoth, California. According to reports, the duo stayed in a house with a group of friends, though they appeared to be coupled up. A source told PEOPLE of the excursion, "Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on." They also said, "Harry was a gentleman and even offered to carry Kendall's snowboard to the ski lift." Talk about a winter wonderland!

Dec. 29, 2015: Harry Styles and Kendall Jenner go on a Caribbean vacation to celebrate the New Year

Styles and Jenner ushered in another new year together two years later when they vacationed in Anguilla in the Eastern Caribbean. The pair were spotted by fans at a restaurant on Dec. 29, 2016, and later seen getting cozy on a yacht . A source told PEOPLE, "There has been a lot of flirting, touching and snuggling going on. They have acted like a couple. They look very cozy and happy."

Jan. 2, 2016: Harry Styles and Kendall Jenner board Ellen DeGeneres' yacht

They continued their vacation when they boarded Ellen DeGeneres and Portia de Rossi's yacht in St. Barts on Jan. 2, 2016. A source told PEOPLE that "things never got serious" between the two when they first met, adding, "He has thought all along that Kendall is hot and was sort of just waiting for a chance to spend more time with her again."

The source also said of the trip, "New Year's worked out perfect, and [Harry] loved it."

Jan. 7, 2016: Khloé Kardashian says Harry Styles and Kendall Jenner are dating

Gotta love when big sisters blow up your spot! Khloé Kardashian said she thought the pair were dating, telling Entertainment Tonight , "They were hanging out together. Do I think they're dating? Yes. I don't know if they're like boyfriend-girlfriend. Nowadays, I don't know, people are weird with stuff. So I don't know their 'title,'" she said, using air quotes. "But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating."

She added that she wasn't sure if they had defined the relationship admitting, "I don't know if they've had that talk yet."

Jan. 23, 2016: Harry Styles and Kendall Jenner attend the same party in West Hollywood

Jenner and Styles attended a private party celebrating music agent Jeff Azoff's birthday at the Troubadour rock club in West Hollywood, California, on Jan. 23, 2016. Jenner's mom, Kris Jenner , and Styles' stepdad Robin Twist were also in attendance.

According to E! News , the Jenners arrived at the club about an hour after Styles and spent another hour inside before leaving. Styles reportedly left the venue later in the night.

April 8, 2016: Harry Styles and Kendall Jenner may have been spotted shopping together in L.A.

A fan claimed on Twitter that Jenner and Styles were seen shopping in Los Angeles together with a group of friends. However, the sighting came just weeks after PEOPLE confirmed Jenner was dating Lakers player Jordan Clarkson and had been for months.

Sept. 1, 2016: Harry Styles and Kendall Jenner have dinner in L.A.

Styles and Jenner were spotted on a date in L.A. on Sept. 1, 2016, with an onlooker saying Jenner was "beaming all night." A source told PEOPLE exclusively the following week that, after getting cozy over the holidays, the pair were "rekindling their old romance," and Jenner was "so excited and happy about it." The source added, "She's always cared about Harry."

September 2016: Harry Styles and Kendall Jenner are "not officially back together"

Styles and Jenner were rumored to be giving romance another try, but the two were taking things slow according to a source.

The source also said Styles and Jenner were "not officially back together" but were "continuing to talk and see where things go."

Jenner remained "hopeful" about her rekindled relationship with Styles but was also "being more careful this time," added the source.

"He's not going to settle down, and she understands that's just the way he is," said the source. "She really likes him, but her heart's not as invested."

Nov. 2, 2016: Harry Styles attends Kendall Jenner's 21st birthday party

Three of Jenner's rumored love interests showed up for her 21st birthday bash at L.A. hotspot Delilah, and Styles was among those in attendance at the star-studded affair. The guest list also included NBA player Clarkson and rapper Travis Scott (though Scott would begin a relationship with Jenner's younger sister Kylie Jenner just months later).

A source told PEOPLE Jenner wasn't with any particular guy and spent equal time with each of them.

"She worked the room and spent a lot of time with Travis in the beginning, then went to Harry for a while," said the insider.

April 18, 2017: Harry Styles hints that his debut album was inspired by Kendall Jenner

In 2017, the "Adore You" singer had fans buzzing when he seemed to allude to his relationship with Kendall in a Rolling Stone article . While talking about his debut, eponymous album of the same year, he mentioned the woman that inspired him. "She's a huge part of the album," he told the magazine. "Sometimes you want to tip the hat, and sometimes you just want to give them the whole cap … and hope they know it's just for them." Could it be that the songs on the album were about Jenner?

May 6, 2019: Harry Styles and Kendall Jenner reunite at the Met Gala

It's not uncommon for celebrities to reunite at fashion's biggest night , but a picture was worth a thousand words when Kendall and Harry were spotted having a conversation inside the event in May 2019. The pair didn't end the night there. In fact, they didn't end the night at all — they joined some other pals and kept the party going well into the next morning, and were spotted leaving an afterparty around 6 a.m.

At the time, a source told PEOPLE that they weren't an item and confirmed that Kendall was still seeing her then-boyfriend, Philadelphia 76ers player Ben Simmons .

The source said of Harry and Kendall, "Harry was her first real relationship, so there is a lot of history there," adding, "but they're just friends."

Dec. 10, 2019: Harry Styles and Kendall Jenner spill their secrets on The Late Late Show

Fans were sent into a tizzy when the pair hung out on camera as Styles filled in for Corden on The Late Late Show and played the ever-so-enlightening game , "Fill Your Guts or Spill Your Guts." The easy chemistry between the two had many wondering if they were still an item or simply really great friends post-relationship.

At one point in the game, after reading the question to herself and admitting, "I'm dying to know this," Jenner asked, "Which songs on your last album were about me?" The audience cheered, but Styles chose to eat cod sperm rather than admit which tracks could be about the TV personality.

Nov. 14, 2022: Kendall Jenner attends Harry Styles' concert in L.A.

Jenner was seen enjoying a night out at Styles' concert with her sister Kylie Jenner and Hailey Bieber . The women were spotted smiling and dancing to Styles' music from the stands in videos shared on social media by concertgoers.

For the outing, the reality star wore a plunging snakeskin halter top while her sister and Bieber sported all-black looks.

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Kendall Jenner, Harry Styles Fuel Romance Rumors, Soak Up the Sun on a Yacht: Pictures

The model, 20, and the One Direction singer, 21, looked cozy as they soaked up the sun. Jenner showed off her runway-ready body in a bikini, while Styles shielded his shirtless torso under a towel.

Related: PHOTOS: The biggest boy bands ever

Earlier in the week, the Keeping Up With the Kardashians star was spotted dining with the boy-bander in Anguilla. The duo, who were first linked back in 2013, hit up a restaurant together on Tuesday, December 29.

A source tells Us Weekly the exes are “hooking up again” now that Styles — who also dated Jenner pal Taylor Swift — has some time off from 1D. Adds another insider: “Now that he has a little hiatus and is on vacation, this is him trying to win her back, and it appears to be working.”

The second source notes that while Styles was the one to call it quits back in 2014, he was drawn back after seeing her in the Victoria’s Secret Fashion Show. “All of his friends were saying how hot and amazing she looked,” the source tells Us.

Related: PHOTOS: Kendall rocks the runway

In any case, both seem to be enjoying the R&R — and Jenner in particular could use it. In a recent post on her app and website, she revealed that she was recently hospitalized for exhaustion, and that she was making a conscious effort to relax in the new year.

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“I guess my resolution would be to chill out more and have the ability to be a little more spontaneous,” she shared. “No matter what, 2016 is going to be the best yet. I can feel it!”

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Kendall Jenner and Harry Styles Just Put Those Romance Rumors Into Overdrive

The romance rumors between Kendall Jenner and Harry Styles are heating up! After causing a frenzy with their recent dinner date in Anguilla on Tuesday night, the two are at it again. The pair looked more than cozy as they soaked up the sun on a yacht together in St. Barts on Thursday. Kendall showed off her fit figure in a bikini while Harry wrapped himself in a towel, and after taking a dip, Harry playfully pulled on Kendall's leg as she tried to climb back onto the boat. They then snuck away to a deck chair and appeared to be cuddling and kissing.

The two were rumored to be dating back in 2013 after stepping out with each other on numerous occasions but never officially confirmed anything. Could it be that the pair is rekindling their supposed romance? See the pictures from their outing here, and then let Harry serenade you with his perfect New Year's Eve performance . Tall

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Harry Styles and Kendall Jenner Are “Leaning on Each Other” After Splitting from Their Partners

The supermodel’s attendance at one of Styles’s recent concerts has some fans raising eyebrows.

Exes Harry Styles and Kendall Jenner are finding comfort in each other after each split from their significant other this past month.

Styles is reportedly on a break from his relationship with Olivia Wilde , whom he had been dating for the past two years since being cast in her psychological thriller, Don't Worry Darling . Meanwhile, multiple outlets recently reported that Jenner and her NBA star boyfriend of two years, Devin Booker , have broken up for a second time.

Now, it seems that Styles and Jenner, who have been romantically linked on multiple occasions starting in 2013, may have rekindled their connection amid their breakups.

"Harry and Kendall have always stayed in touch, but in light of their recent splits, they have more time for one another," an insider told The Sun . " And Harry has had Kendall's ear over his break-up with Olivia. Kendall is one of the few people to understand the level of fame and scrutiny which Harry endures. She is also dealing with her own tough time."

The Sun also noted that the two have been "leaning on each other" in the past few weeks.

The former flames have maintained a friendship long after their romance ended. Back in 2019, Jenner even made a guest appearance on The Late Late Show when Styles filled in for host James Corden.

Fans have been speculating about the former couple since Jenner attended one of Styles's Los Angeles concerts earlier this month. Video footage captured the model dancing alongside friend Hailey Bieber and sister Kylie Jenner, and one viral TikTok even alleged that the singer blew a kiss to Jenner during his song "Love of My Life" (which many believe is about her).

Still, The Sun 's source added that their renewed post-breakup connection may just be platonic.

"Close as they are, Harry and Kendall found dating difficult, and all of those practical problems they faced years ago are still there," the source continued. "That said, their friends speculate that they might hang out over the holidays. In the past they have gone away together shortly after respective break-ups, so they could very well end up on a yacht soaking up the sun in the next couple of months."

As an associate editor at HarpersBAZAAR.com, Chelsey keeps a finger on the pulse on all things celeb news. She also writes on social movements, connecting with activists leading the fight on workers' rights, climate justice, and more. Offline, she’s probably spending too much time on TikTok, rewatching Emma (the 2020 version, of course), or buying yet another corset. 

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Kendall Jenner and Harry Styles Definitely Celebrated New Year's Eve Together

There's an old saying — or one that's as old as season two of The OC — that the way you spend New Year's Eve is how you'll spend the whole year. If there's any truth to that, and there's always truth to The OC , 2016 is going to be the year of #Hendall.

Harry Styles and Kendall Jenner celebrated the last day of the year together on a luxury yacht in St Barth's.

They giggled.

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They whispered sweet nothings. ("I missed you this much." — Harry, probably.)

They wore jaunty hats...

...and matching circle-framed sunglasses.

They bathed in the sun sharing a single lounge chair. (Apparently no matter how luxury the yacht was, there was a shortage of lounge chairs.)

And they brought both of their mothers along for the fun.

Now that's a midnight toast we'd like to see. Where's the long-lens paparazzi when you really need them? (Just kidding, invasion of privacy is bad but witnessing Kendall, Harry, Kris Jenner, and Anne Twist ring in the New Year would be so, so good.)

RELATED: Harry Styles and Kendall Jenner Are Reportedly Spending New Year's Together

For more One Direction, watch these videos:

Kendall Jenner and Harry Styles PICTURED kissing on luxury yacht ahead of New Year celebrations

The snaps show the pair go into full PDA mode, and it's one of the first times they've been snapped in a steamy clinch

• 11:51, 1 Jan 2016
• Updated 13:32, 1 Jan 2016

Kendall Jenner and Harry Styles have been pictured sharing an intimate embrace ahead of the New Year's celebrations this week.

The pair were snapped kissing and cuddling as they struggled to keep their hands off each other on a sun lounger, smashing rumours once and for all that they're just good friends.

Rumours of a romantic reconciliation between them went into overdrive just days ago after a video emerged of the pair getting very cosy over dinner.

Now the new snaps have sent fans into meltdown, as a bikini-clad Kendall lies over Harry and they appear to share a lengthy kiss.

Kendall and Harry - who were first romantically linked back in 2013 - are holidaying with pals on Caribbean island of Anguilla.

Kendall was snapped in a skimpy bikini and sunglasses, wearing her hair up in a messy ponytail and appearing relaxed and happy as she lounged next to the One Direction singer.

Meanwhile Harry wore loose white swim shorts, and tied his own hair back for the outing.

They weren't alone however, as Harry invited his mum along too - so it must be getting serious.

Anne shared a photo on what appears to be the same luxury yacht last night, signalling they all could have remained onboard for the New Year's Eve celebrations.

It is thought the pair rang in the New Year together on the yacht, and they were certainly in the mood for celebrating.

Fans noticed as well as the pair being overly tactile, they appeared to only have eyes for each other and were seen locked deep in conversation.

While some fans celebrated the happy couple, others were heartbroken.

One devastated fan wrote: "Those pics of Harry and Kendall need to find the exit sign and leave my timeline."

Another wept: "THESE HARRY AND KENDALL PHOTOS ARE RUINING MY NEW YEAR.

The pair first sparked romance rumours in 2013 when they were snapped on a dinner date in Hollywood.

The close friendship ran right through to 2014, as they were eventually pictured on the sliopes together - but whikle they appeared closer than ever, they never confirmed the romance.

Well, there's no denying the chemistry in these photos.

MORE ON New Year Kylie Jenner Kendall Jenner Harry Styles Harry Styles and Kendall Jenner

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Harry Styles and Kendall Jenner Spending New Year’s on Ellen’s Yacht Doesn’t Mean They’re Dating

Whatever you did for New Year’s—however raucous and well-attended your party was, however thrilling it was to stand with a million other people as 2016 descended upon Times Square—it cannot compare to how Harry Styles and Kendall Jenner, two young people of impossible beauty and wealth, spent their holiday. Because they were on a yacht in St. Barth’s with Ellen DeGeneres and Portia de Rossi for at least part of it. You can’t beat that, can you? Don’t even bother trying to compare! Seeing the wonder in your child’s eyes as he or she, finally old enough to stay up until midnight, first realized the bittersweet cheer of time groaning on? Nope, not as good as a yacht in St. Barth’s. A romantic evening with a special somebody, all fluttery with champagne and possibility, when it began to feel like you maybe want to spend every coming year twined up together, until the end of it all? Sorry, did you hear the part about Ellen?

So, Harry Styles and Kendall Jenner had a pretty great New Year’s. But! Their being on that yacht together: What does that mean ? Are they an item? Naturally, photos of the pair on this fabled yacht have been swirling around the Internet for a few days now, like leftover confetti in the wind, and have set people speculating. For good enough reason. In the photos, Styles and Jenner seem to share a certain intimacy, a familiarity, that could suggest a romantic relationship. But! Let’s not get ahead of ourselves, as we always tend to do.

People magazine, probably as reliable an outlet for truth in these matters as exists these days, quotes a source who says that this was just a friendly trip to Ellen’s yacht. “Harry also vacationed with friends, so it wasn't just a romantic vacation for Harry and Kendall,” the source tells the magazine, which traces Styles and Kendall’s friendship to a meeting two years ago. Apparently Styles did invite Jenner on the New Year’s vacation, she flying in from Los Angeles, but that doesn’t necessarily mean anything. Just because you invite someone to hang out on Ellen and Portia’s yacht off the coast of an exclusive, celebrity-filled Caribbean island for New Year’s doesn’t mean you want to date them.

Maybe this was just a friendly hang. Why a middle-aged married couple was hanging out with a 21-year-old boy-band member and a 20-year-old socialite/model on a yacht over New Year’s is really anyone’s guess. But if People ’s source is to be believed, we at least know that there was no hanky-panky going on between the boy-bander and the socialite/model. Or, at least, that hanky-panky wasn’t the express purpose of the trip. Hanky-panky may have occurred—the source does not strictly say that it didn’t—but whatever did or didn’t happen, this was not intended, solely, to be a romantic getaway.

That’s what we know at the moment. From our pitiful remove, anyway. As we stare longingly through our super-binoculars, spying on these happy angels from all the way up here in the frigid north. These pretty and fabulous young people frolic in the realms of mystery, their hearts and minds unknown to us chattering nobodies, their bodies warmed by a fuller, kinder sun than what shines its dim rays on us. Maybe up close everything makes sense—in proximity, it’s clear just where Harry and Kendall stand in relation to one another. But we’ll probably never know that closeness. Not most of us, anyway. So we guess on, like yachts against the current, borne back ceaselessly into our caste.

Kendall Jenner, Amy Schumer, and More: The 2015 “It Girls”

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Kendall jenner & harry styles -- all hands on deck (photos), kendall jenner & harry styles all hands on deck.

Kendall Jenner and Harry Styles became extra familiar with each other on a luxury yacht in St. Barts.

The two were spotted Wednesday getting handsy after reports surfaced they'd been vacationing together in Anguilla the night before.

It's unclear if the two are "officially official" but judging by the pics, the 20-year-old supermodel and 21-year old pop star certainly have no problem packing on the PDA.

Anchor's aweigh.

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Here's What Happened With Kendall Jenner And Harry Styles' Relationship

They're undisputedly two of the most beautiful people in the world, and frequently run in the same A-list Hollywood circles, so it makes total sense that Kendall Jenner and Harry Styles were a thing, even if their relationship was short-lived. 

As Grazia notes, the supermodel and former One Direction star were first linked back in 2013 and their initial dalliance was actually the beginning of Styles being linked with several Victoria's Secret Angels, including Sara Sampaio and Georgia Fowler. 

In the years since their romantic relationship ended, Jenner and Styles have remained close friends, memorably crossing paths at the 2019 Met Gala and even hosting a glamorous after party together. As Page Six reported, the fiesta was totally spontaneous, with an insider admitting, "The party came together very last minute. This was expected to be Harry and Kendall and a few close friends, but it became a huge group of A-listers." And evidently, there's still love between these two. 

Harry and Kendall were romantically linked for several years

The duo stepped out in public together again at the British Fashion Awards in London in December 2014, following it up with a New Year's vacation in Mammoth, California. An eyewitness described them as "very cute" and confirmed there was "a lot of flirting" going on. 

A couple years later, model Kendall Jenner and former boybander Harry Styles were snapped taking a vacation together, snuggling up on a yacht, and enjoying more intimate date nights. "They have acted like a couple," a source advised at the time. "They look very cozy and happy." During a New Year's 2016 celebration in St. Barts, an insider revealed Styles always fancied Jenner and was simply waiting for the right time to pursue a relationship with her.

According to People , following his highly publicized relationship with Taylor Swift in 2017, Styles was linked to Jenner again after the two were spotted sharing a romantic meal together and leaving the restaurant in his car in December 2019.

Although a source clarified they were "just friends" at the time and the "Keeping up with the Kardashians" star reiterated her single status, the rumor mill went into overdrive.

Kendall and Harry remain close friends

If anyone was confused and on the fence about if Harry Styles and Kendall Jenner were an item, the model's older sister Khloe Kardashian confirmed the coupling in 2016. "Do I think they're dating? Yes," Khloe told Entertainment Tonight  Kevin Frazier at the time. "I don't know if they're like boyfriend-girlfriend. Nowadays I don't know. People are weird with stuff. So, I don't know their title. But I mean, they were in St. Barts together hanging out, so to me that's dating."

Styles himself also seemed to hint at Jenner being the inspiration behind his 2017 debut album during a Rolling Stone interview, stating, "She's a huge part of the album," but by the release of the project, the relationship was already over. The former couple reunited twice in 2019, first at the Met Gala and then while appearing on "The Late Late Show with James Corden," per Entertainment Weekly . 

That same year, a source confirmed to Us Weekly that the two remained on excellent terms, noting, "Harry and Kendall are great friends and always have been." Although both of them remain super busy, so they don't hang out that often, the insider revealed, "When they do, they always have a blast. It's an easy, super chill friendship." 

As Glamour magazine notes, in 2021, Kris Jenner finally confirmed once and for all the duo had indeed been an item, during a virtual appearance on "The Ellen DeGeneres Show" – as if we didn't already know. 

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Spotted: Kendall Jenner and Harry Styles Getting Handsy on a Yacht

The most flirty exes you'll ever see.

Update, 12/31: Well, here's another clue Kendall Jenner and Harry Styles may be on something more than just a friendly, platonic vacation in the Caribbean. The two were photographed on a yacht together in St. Barts, being exceptionally handsy. Harry was shirtless; Kendall was in a bikini.  Daily Mail posted pics that included Harry grabbing Kendall's wrists and feet , Kendall resting her model legs on him, and the two gazing right at each other, faces oh-so very close .

The most suspiciously flirty exes, indeed . Kendall's face says everything...

12/30:  Way back in the late days of 2013, Kendall Jenner and Harry Styles were rumored to be dating…or, as Harry clarified  in an interview , were dating- ish : "I mean, we went out for dinner, but no, I guess."

Fast forward two years, and the two are getting dinner together agaaain , this time on the British island of Anguilla in the Caribbean, E! reports   with  exclusive photos of the date. A restaurant-goer also confirmed it happened yesterday evening:

Soooo, is this trip a friendly get-together or a secret romantic getaway? Unclear , but here are some clues: Kendall Jenner is now a highly coveted top model, with a New Year's resolution to "find a boyfriend, but it's not legit at all, lol." Harry Styles is on hiatus from his five-boy-turned-four-boy band One Direction and is  on the market . 

And elsewhere, Kendall's close friends Justin Bieber and Hailey Baldwin are also on vacation, deliberately blurring the lines between love and friendship, playing with our minds, etc.: 

Alyssa Bailey is the senior news and strategy editor at ELLE.com, where she oversees coverage of celebrities and royals (particularly Meghan Markle and Kate Middleton). She previously held positions at InStyle and Cosmopolitan. When she's not working, she loves running around Central Park, making people take #ootd pics of her, and exploring New York City.

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Serious Question: Why Are We Obsessed With Yacht PDA?

After Aperol Spritzing through Tuscany, Harry Styles and Olivia Wilde surfaced on a yacht this week. They kissed; they nuzzled; they possibly danced (or, alternate theory, simply clung to each other for balance). The couple, who met on the set of Wilde’s second directorial effort, Don’t Worry, Darling , even left their big boat so that an artfully mustachioed Styles could captain a smaller vessel through glittering Mediterranean waters. In my estimation, the Styles fandom lost at least a full afternoon’s worth of productivity to a forensic examination of this photo set. All I could think, to quote Courteney Cox in Scream 2 , was: It’s happening again .

After all, it’s July, also known as yacht season, an annual micro-season within summer in which super-celebrities and moguls embark on luxe floating vacations, often with sparkling, sexual overtones. Styles and Wilde join a long, storied tradition (one well documented on many episodes of The Ringer’s Jam Session podcast ) that includes Styles himself and Kendall Jenner, along with both of their mothers, off the coast of St. Barts in 2016. Beyoncé has been known to yacht dive from great heights (once from an aptly titled rental yacht named the Halo) on yachting jaunts with Jay-Z to Capri and Croatia. In 2019, Timothée Chalamet and Lily-Rose Depp ardently made out aboard a yacht off Capri, as Italy is the unofficial global epicenter of yacht season. After two terms in the White House, Barack and Michelle Obama decamped to David Geffen’s superyacht , the Rising Sun (or as he prefers, “R.S.”) in Tahiti, which is how we’d all decompress after eight years of Mitch McConnell if we could. 

It must be said that while the appetite and voyeurism for yacht-season photo evidence is strong, there are also persistent ethical questions about breaches of privacy. Yachts are at once one of the only places celebrities can be entirely alone—save for the prying eyes of long-lens paparazzi. And yet couples sunning and smooching are often accused of doing it for publicity, a murmur that Chalamet, for one, denied. In an interview with GQ , he recalled “waking up to all these pictures, and feeling embarrassed, and looking like a real nob .... And then people are like, ‘This is a P.R. stunt.’ A P.R. stunt ?! Do you think I’d want to look like that in front of all of you ?!”

There is something endlessly fascinating about yacht PDA, as well as platonic group yacht vacays (see: Oprah and Gayle King aboard the R.S. , on which Geffen notoriously quarantined) . Much of modern celebrity culture, from the aughties zenith of Us Weekly to the present, is predicated on a kind of imagined relatability. Stars—at least occasionally—are like us. They go to Starbucks, sometimes wearing Juicy jumpsuits. They walk their dogs. But most spectators will never find themselves lolling starboard, à la Styles and Wilde, on a yacht near Monte Argentario. It’s like glimpsing a Gatsby party from the other side of the Long Island Sound—not easy to look away. Of course, yacht-watching can border on grotesque. Amazon employees had to fight hard for their $15-per-hour rate; meanwhile, Jeff Bezos’s $500 million superyacht comes with a support yacht complete with its own helipad.

With the rise of Bennifer 2.0 , I can’t not think about the scenes from the now vintage “Jenny From the Block” video in which Affleck, in all of his pompadoured glory, caresses Lopez’s bikini bottom sur la mer . It was a bit of celebrity satire—a nod from two celebrities who never fail to feed the beast. In the spirit of second chances, here’s hoping for the real thing in 2021. 

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Harry Styles And Kendall Jenner Had A Very Revealing Dinner Date

Off a yacht and into the deep end, because Harry Styles and Kendall Jenner had a dinner date and went in on disclosing some home truths.

Taking over from James Corden to play host on the Late Late Show , Harry invited his long-time pal Kendall to have a second swing at the show's “Spill Your Guts” feature, which sees contestants having to answer some invasive, all-revealing questions or eating some obscure delicacies like salmon smoothie or the I' m A Celeb -style animal genitalia.

Naturally, conversation quickly turned to the pair's pre-existing relationship with Kendall asking the question — as written by the show's producers — “Which songs on your last album were about me?”

Harry evidently did not see the question coming and hid his face in his manicured hands immediately, before tucking a napkin in his Gucci collar and gnawing down on some cod sperm. “What are we doing?” he laughed as he struggled with the forfeit.

Read More: We’ve Listened To Harry Styles’s ‘Fine Line’ Album And This Is What You Need To Know

Other awkward questions that saw the pair reaching for the plate and not giving the truth was Harry asking Kendall: “You're the highest paid supermodel in the world, who is the most unlikeable supermodel in the world?” Ever the professional, Kendall admitted that she has the answer but avoided sharing it and immediately sipped at her unpalatable salmon smoothie. Next, Kendall went on to ask Harry to rank the music of his One Direction peers’ solo efforts but the 25-year-old musician instead opted to chew down on a giant water scorpion.

With their tête-à-tête complete, the pair headed over to the Late Late Show sofa to be joined by Tracee Ellis-Ross to continue the question time. As host, Harry led the conversation and produced a photograph of Kendall in her teenage years holding a One Direction sign and demanded context on the photograph, with the 23-year-old model admitting that she had been “asked” to make the sign, rather than having made it off her own back as a serious Directioner. Okay Kendall, if you insist.

More from British Vogue...

Never Forget Harry Styles and Kendall Jenner's PDA-Filled Yacht Vacation

There's a reason why kendall jenner and harry styles' joint appearance on the late late show went so swimmingly..

There's a reason why  Kendall Jenner and Harry Styles ' joint appearance on  The Late Late Show went so swimmingly. 

The singer filled in for  James Corden as a guest host on Tuesday's episode, during which he and the  Keeping Up With the Kardashians  star played Spill Your Guts or Fill Your Guts . During the segment, Kendall agreed to rank her siblings according to their parenting skills, while Harry opted to consume cod sperm  rather than answer her question of which songs on his last album are about her.

Kendall, 24, and Harry, 25, go way back and have occasionally sparked dating rumors on and off since 2013. Over the New Year's holiday in 2016, the two got cozy on a luxury yacht while vacationing together  in St. Barts. The two were also joined by Ellen DeGeneres  and wife  Portia De Rossi .

"Why are they a good match? Well, they're both super hot, super great, sweet people," Kendall's sister Khloe Kardashian later told E! News . "And if I'm on a yacht in St. Barts if I'm—how old is she, 20? He's 20?—hey, I ain't mad at you, Kenny. Do your thing, girl!"

See photos from Kendall and Harry's Caribbean vacation:

The two show some PDA a yacht in St. Barts.

The two enjoy some R&R.

Kendall stunned in a white bikini.

The two gaze at the sea.

The  One Direction singer grabs the reality star's foot playfully.

The reality star climbs aboard, with little help from the singer...

The reality star shows off her trim figure in a crimson two-piece.

The reality star adjusts her bikini top.

The reality star covers up in the wind.

Ellen DeGeneres & Portia De Rossi join the reality star and  One Direction singer, who have sparked romance rumors for two years, for lunch on a yacht in St. Barts on New Year's Day.

Weeks later, Kendall and Harry attended a private party  at the Troubadour rock club in West Hollywood with her mother Kris Jenner . The two appeared to cool things off for a few months. In April 2016, a source told E! News that they were "hanging out again," but were not "officially dating."

In January 2018, Kendall attended Harry's concert in Los Angeles with friends and was spotted dancing and giving him a standing ovation .

This past May, the two rumored exes were all smiles as they  reunited at the 2019 Met Gala .

Watch  Keeping Up With the Kardashians on Sundays at 9/8c only on E!

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