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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

Updated on 1/3/2016 at 10:30 AM

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 Spending New Year’s on Ellen’s Yacht Doesn’t Mean They’re Dating

By Richard Lawson

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.

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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 12:06, 1 JAN 2016

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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.

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

By Casey Lewis

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:

By Sandy Aziz

By Kara Nesvig

By Kerry McDermott

By Marci Robin

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.

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Kendall Jenner and Harry Styles yacht pics resurface as he kisses Emily Ratajkowski

Harry Styles has broken hearts around the world as he’s seen spotting Emily Ratajkowski, leading to the OG heartbreak pics of him and Kendall Jenner kissing on a yacht resurfacing.

One Direction fans around the world have the photos of the two engraved in their heads, which came to light years after Kendall Jenner and Harry Styles rumors first started spreading. Since then, the two have been romantically linked to a number of different people, and it now seems dreams of reconciliation are further away.

We take a trip down memory lane and take a look back at the yacht pictures that broke the internet.

• OMG: Kendall Jenner’s headscarf post receives backlash from fans

Harry Styles was spotted kissing Emily Ratajowski in Tokyo

Not long after his breakup from Oliver Wilde, Harry Styles was spotted in Tokyo kissing Pete Davison ‘s ex Emily Ratajkowski.

Emily was the first girl Pete was linked to after breaking up with Kendall’s older sister, Kim Kardashian .

The two were spotted dancing with each other as they sheltered from the rain in Japan as Styles is currently in the capital for his Love On Tour series of worldwide gigs.

Harry and Kendall stans hoped for the two to reconcile their love as the model ended her relationship with Devin Booker around the same time as the singer became single.

She was then also spotted at one of Harry’s concerts, and hopes of a reconciliation were higher than ever.

However, it now seems the two have both moved on with other people, as Kendall has recently been linked to Bad Bunny .

Harry Styles and Emily Ratajkowski spotted kissing in Tokyo. pic.twitter.com/F2PXeK7wli — Pop Base (@PopBase) March 26, 2023

Kendall Jenner and Harry Styles yacht photos resurface

The iconic Kendall Jenner and Harry Styles yacht pics were first released at the end of 2015, when the pair were spotted kissing on Ellen Degeneres ‘ yacht in St. Barts.

The photos broke the internet and teenage hearts around the world, as the two were photoed getting very close. They were seen lying on the sunbeds with their arms around each other and even spotted hiding underneath a towel as things got steamy.

Jenner and Styles first sparked dating rumors in 2013, when they were spotted out a number of times together, whilst Harry was still in the band.

In an interview for their album at the time, Midnight Memories, Harry was asked if he was dating Kendall to which he responded: “I mean, we went out for dinner, but no. I guess.”

Although the two never publically confirmed their relationship, they were spotted together a number of times.

In a game of Spill Your Guts Or Fill Your Guts on The Late Late Show in 2019 Kendall seemed to indirectly confirm the romance when she asked Harry which songs on his last album were about her.

The questions led to cheers in the crowd as Harry Styles tucked into cod sperm to avoid the awkward answer.

Harry and Kendall Jenner spotted on a yacht in St Barth's earlier. pic.twitter.com/gFHGApEvF2 — best harry pics (@harryphotoss) December 31, 2015

• WOW: Kris Jenner and Harry Styles fans are Late Night Talking after concert

Fans brand Harry a ‘bad kisser’

From being in arguably one of the biggest boybands of all time to launching a highly successful solo career with some acting on the side, it seems like Harry Styles can do it all.

However, it seems like his talents may not extend to kissing as some fans have picked up on.

The suspicions come to light every time a new picture of the star kissing a new love interest is released, and it seems like the rumors have crushed One Direction fans’ dreams.

Not that anyone asked or anything but Harry Styles is a bad kisser 😭 did y’all see that man it was giving minimal effort 😭 — Jamie🌻 (@Jamieemunozz) March 27, 2023

harry styles being a bad kisser has changed my brain chemistry for good i cannot process this — nikola (@noplanik) March 27, 2023

Harry styles lowkey bad kisser ?? That video was painful to watch — 🖤🥂 (@jennifreda) March 26, 2023

Well, we guess you can’t have it all.

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All aboard the love boat: Kendall Jenner shares a kiss with former flame Harry Styles as they get VERY cosy on luxury St Barts yacht

By Joanna Crawley and Becky Freeth for MailOnline

Published: 06:47 EST, 1 January 2016 | Updated: 22:25 EST, 1 February 2016

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They sparked rumours of a romantic reconciliation earlier this week when they were spotted by fans at a restaurant in idyllic Anguilla on Tuesday night.

But if there was any doubt over Kendall Jenner , 20, and Harry Styles ', 21, reignited romance they seemed to be put to rest on Thursday when the pair were captured in a romantic clinch as they prepared to ring in the new year with each other's company.

The Keeping Up With the Kardashians star was seen lounging on the One Direction singer before leaning in for a kiss as they enjoyed another day together on a luxury yacht in St Barts. 

Scroll down for video 

Back together? Harry Styles (right, seated) and Kendall Jenner left) fuelled reconciliation rumours on Wednesday after pictures appeared to show them in an intimate clinch during a romantic getaway in St Barts

Like most lovers ringing in the New Year, Harry and Kendall seemed to share a kiss not long after she cuddled into him with her long limbs straddled around him. 

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The brunette seemed to nuzzle his head before resting hers on his chest as they lay out on the sun deck surrounded by friends, who just passed by and didn't distract them from each other for a second. 

Kendall showed off her model body in a tiny pink bikini as the pair relaxed on board, keeping cool in a pair of shades. The reality star's mother Kris Jenner was also spotted joining the fun yacht party, while Harry was spotted with his arm around his mum Anne.

See more of the latest pictures of Kendall Jenner and Harry Styles as they spark romance rumours in St Barts

Hanging out: Kendall and Harry, who previously dated fleetingly according to reports in 2013, seemed comfortable in each other's company

Love is in the air? Kendall rested her head on Harry's with a contented look on her face, before leaning in for a kiss

Getting hot out here: Kendall couldn't keep away from the popular boybander as she nuzzled into his head

The former rumoured couple were first seen enjoying a romantic dinner at Blanchards restaurant on another Caribbean Island, earlier this week, just days after Harry embarked on a hiatus from the chart-topping pop group. 

The high-profile pair were first rumoured to be dating back in 2013 when they were spotted enjoying a string of outings together. 

In an interview with the band in the same year, dubbed 1D Day to promote third album Midnight Memories, Piers Morgan asked Harry: 'Are you dating Kendall Jenner, yes or no?'

Meeting the parents: Harry slung an arm around his mum Anne as he soaked in his surroundings while Kendall's mother Kris Jenner was also spotted on board the yacht on Thursday 

Cute couple: The pair couldn't stay away from each other despite being joined by a number of pals

Going under cover: Harry pulled a towel off the lounger so they two could have some privacy away from their friends

Something to hide? The duo hid behind one of their navy blue beach towels as things got steamy on the sun lounger

Cuddles: The duo sought comfort in one another and she rested her head on his chest and neck at one time

New Year's kiss? The model and singer shared numerous kisses and hugs as they waited to ring in 2016

Handsome couple: If they were to become the new couple, they would certainly make a handsome one

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The singer tentatively replied: 'I mean, we went out for dinner, but no. I guess.' 

Pushing for more, Piers continued: 'Did I hear in Los Angeles, a hot date? Budding romance?' while a flustered Harry responded: 'Dunno', before a male voice off-camera shouted 'move on! move on!' 

Prompting Harry to say: 'Yeah, let's move on shall we?'

Defending his probing, the journalist said: 'It's supposed to be tough questions.

This is the life: The pair were in a world of their own despite being surrounded by mutual pals

Pensive: The duo looked out to sea as they prepared to ring in 2016 together

Playful: They spent time playing games as they passed the time at sea

 Distracted: Thought there were plenty of people around them, they seemed only concerned with each other

Well red: Kendall showed off her exquisite figure in a skimpy bikini on the boat as she went to enjoy a selection of carby treats

Wonder what they're talking about? Kendall, wrapped in a slinky kimono, chatted to the tattooed pop star under the beaming sun

Cooling off: Harry sipped from a cold drink as they pair chatted in the beaming sunshine

Rest and relaxation: Harry played on his phone as Kendall lounged on his chest during the boat trip

'You're boring,' the unknown voice jokingly interjected.

But despite all the speculation, the pair never went on to officially announce a relationship, instead they insisted they were just friends. 

Though their romance was thought to be fleeting, they certainly seemed comfortable in each other's company on the holiday and flirted outrageously in the pictures.

Kendall bit down on her lip as Harry grabbed her by the wrists and rocked her back and forth. 

Wild: Kendall paired her pink bikini top with leopard print bottoms as she hit the water with pals

In a world of their own: Harry and Kendall only had eyes for each other despite holidaying with friends

Just the two of us: Kendall couldn't take her eyes off her handsome former beau, who she was first linked with in 2013

Inked: The One Direction star showed off his extensive tattoo collection as he stripped down to swimming shorts and shades

Caught her attention: Top model Kendall giggled as Harry entertained her with a story

Leaning in: There wasn't much room for talking though as the pair resumed their kissing and cuddling

What stunner: Kendall showed off her model figure in her tiny two-piece as she topped up her tan

Blissful: The reality star couldn't hide her smile as she relaxed side by side with the Brit singer

Happy New Year: It looked as thought the pair were planning to see in 2016 together

It's not also not a pure coincidence that the famous duo are catching up after so many years, because Kendall's model BFF Gigi Hadid, 20, is currently dating Harry's ex-bandmate Zayn Malik, 22.

Their circles have seemed to overlapped many times over the years, with Harry also previously being linked to their mutual pal Cara Delevingne in September 2013. 

Kendall's mother Kris Jenner has also been holidaying St Barts recently, while Harry's bandmates are in the UK enjoying the early throes of their new-found freedom.

Super close: Despite not being seen together for awhile, Kendall and Harry have remained close since first being spotted on a date in 2013

Four's a crowd? The pair's pals didn't seem to mind the PDA from the cute couple

What's going on? Despite all the speculation, the pair never went on to officially announce a relationship back in 2013, instead they insisted they were just friends

Is this it? The pair may be kicking off 2016 as a couple after their romantic holiday together

Love boat: The pair barely left each other's side during the day at sea in St Barts 

Getting comfy: Kendall lounged on Harry as she showed off her figure in her pretty pink bikini 

Getting steamy: Though their romance was thought to be fleeting, they certainly seemed comfortable in each other's company on the holiday and flirted outrageously in the pictures

And relax: After a hugely busy year with his band Harry looked delighted to have some downtime with his pals

Exciting year ahead: As One Direction prepare for their extended hiatus next year, Harry will have more free time to spend with Kendall 

Share or comment on this article: Kendall Jenner kisses Harry Styles while holidaying on St Barts yacht

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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. 

Harry Styles and Kendall Jenner’s Full Relationship Timeline

See the highlights from their sweet young love and lasting friendship.

The 2010s romance between Kendall Jenner and Harry Styles was a moment, but in the years that have followed, whether as secret lovers or just friends, the two have continued to share a special kind of chemistry.

Jenner was one of the singer's first serious partners and frequent muse, while Styles was the supermodel's sweet musician boyfriend of her late teen years. The two first began their romance toward the end of 2013, before opting to amicably remain friends several years later.

Below, look back on the supermodel and singer's young love, and watch this space for updates surrounding their potential reconciliation.

November 14, 2022: Jenner attends Styles's concert.

Jenner happily supports Styles at a concert in Los Angeles, where the supermodel is captured dancing to the singer's music on the stands beside best friend Hailey Bieber and sister Kylie Jenner.

Videos shared by fans on social media seem to show Styles blowing Jenner a kiss during his performance of "Love of My Life," which is speculated to be about her.

December 10, 2019: They make a joint appearance on The Late Late Show .

The exes demonstrate their effortless, lasting chemistry via a joint appearance on The Late Late Show with James Corden , during which the two play the popular game Fill Your Guts or Spill Your Guts.

Per the game's rules, the two interrogate one another with a series of uncomfortable questions—including one about which songs from Styles's 2017 album were specifically about Jenner—which they either truthfully answer or pass to taste a selection of unappetizing foods.

The flirting is enough to make you blush.

May 6, 2019: They hang out at the Met Gala.

The two interact closely with one another throughout the annual fashion event, and are later spotted leaving an after-party together with friends at 6 a.m. the next morning, according to sources .

Their public reunion sparks rumors of a potential rekindled romance—though according to a People insider, the two are still not an item. "Harry was her first real relationship, so there is a lot of history there," the source says at the time, adding, "but they're just friends."

April 18, 2017: Styles confirms Jenner is his muse.

In a feature with Rolling Stone , the singer reveals that now-ex Jenner was a direct source of inspiration for his May 2017 debut studio album. "She's a huge part of the album," he tells the magazine, while sweetly adding, "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."

November 2, 2016: Styles celebrates Jenner's 21st birthday.

The singer is spotted at Jenner's star-studded birthday bash at Delilah in Los Angeles, where Jenner's other rumored ex Jordan Clarkson is also in attendance .

September 1, 2016: They go on a dinner date as friends.

Jenner and Styles—who broke up some time earlier this year—are spotted out together again for a dinner date in Los Angeles, where Jenner is reportedly "beaming all night."

Their outing sparks rumors that the two may be rekindling a relationship, but a source later tells People that they are "not officially back together" and just "continuing to talk and see where things go."

The insider adds that while Jenner is "hopeful" about rekindling a relationship with Styles, she is also acting more cautious. "He's not going to settle down and she understands that's just the way he is," the source says. "She really likes him, but her heart's not as invested."

December 29, 2015–January 2, 2016: They ring in their second New Year's together.

The two are spotted getting cozy aboard several yachts throughout a Caribbean holiday vacation. "There has been a lot of flirting, touching and snuggling going on," an onlooker tells People . " They have acted like a couple. They look very cozy and happy."

"New Year's worked out perfect, and [Harry] loved it," another source says of the trip—adding that while the two have never been serious before this point, Styles was always attracted Jenner and has been "waiting for a chance to spend more time with her again."

Days later on January 7, Jenner's elder sister Khloé Kardashian seemingly confirms that the two are an item in some way. In an exclusive with Entertainment Tonight , she tells the outlet that she bets that the two of them are dating, even though she isn't sure whether Jenner and Styles have actually had "that talk" yet.

"They were hanging out together. Do I think they're dating? Yes. I don't know if they're, like, boyfriend-girlfriend," Kardashian says. "Nowadays, I don't know, people are weird with stuff. So I don't know their 'title,'" she adds with air quotes. "But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating."

January 1, 2014: They bond on the slopes.

Jenner and Styles ring in the new year alongside friends with a ski trip in Mammoth, California, where they reportedly spend a lot of one-on-one time together. The two are not yet officially together at this point, but according to onlookers, an evident attraction is there.

"Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on," a source tells People . "Harry was a gentleman and even offered to carry Kendall's snowboard to the ski lift."

November 20, 2013: They first spark rumors of a romance.

For their first captured night out, an 18-year-old Jenner and 19-year-old Styles are photographed in the singer's car following a date night at Craig's restaurant in West Hollywood. The dinner spurs the first rumors of a romance, though Jenner later clarifies on Twitter that she is, indeed, still single. "They're just friends," a People source also claims at the time.

Though, several weeks later, on December 1, 2014, they are spotted again together with friend Cara Delevingne at the British Fashion Awards held at the London Coliseum.

Sabrina Park is a Digital Fellow at HarpersBAZAAR.com where she covers news, fashion, and culture stories. When she’s not writing she loves hanging out with her cat, reading outdoors and scrolling the depths of TikTok.

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Serious Question: Why Are We Obsessed With Yacht PDA?

By Michelle Ruiz

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. 

Vogue Daily

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Why Did Kendall Jenner and Harry Styles Break Up? Inside Their Split

Take a walk down memory lane and look back at the relationship between harry styles and kendall jenner plus, learn about where the two stars stand now..

Kendall Jenner and  Harry Styles are two of the most famous 20-somethings in the world. So, naturally, the two have crossed paths — and even been linked romantically! Rumors about the two being an item circulated in 2013, and the pair were seemingly on-and-off until 2016. All of these years later, fans still love to reminisce about those “Hendall” days. Keep reading to learn the reason why Kendall and Harry broke up and what their relationship is like today.

Why Did Kendall Jenner and Harry Styles Break Up?

Kendall, 28, and Harry, 29, have never revealed the real reason for their split. In fact, the two stars never outright confirmed that they were together. At the time of their breakup, it was reported that their “busy schedules” caused the demise of their relationship. They allegedly broke up in 2016, the same year that Harry’s band  One Direction  went on hiatus. Kendall, meanwhile, was busy with modeling and filming  Keeping Up with the Kardashians  at that time.

In 2019, Harry appeared on  The Ellen DeGeneres Show and was awkwardly asked about his relationship with Kendall. The “Fine Line” singer claimed that he was never romantically involved with the supermodel, which Ellen DeGeneres didn’t appear to believe. “Yeah, we’ve been friends for um, a while now, yeah. Like several years,” Harry said.

How Long Did Kendall Jenner & Harry Styles Date For?

Kendall and Harry seemingly first got together towards the end of 2013. The romance was, at first, fairly short-lived, and the two split in February 2014. They did, however, rekindle their romance sometime in 2015, before apparently calling it quits in 2016.

During their time together, Kendall and Harry definitely had a few memorable moments. One that stands atop the list for many “Hendall” shippers is totally their time canoodling on a yacht in St. Barts back in December 2015. The two definitely appeared to be super smitten with one another at the time, when their relationship was seemingly back on after going their separate ways that prior February in 2014. They were also memorably spotted in Anguilla just days prior to their St. Barts trip. Apart from their time together as a couple, they’ve also had some great run-ins post-romance. The two just happened to bump into one another at the 2019 Met Gala, where they were all smiles as they chatted and reconnected.

Are Kendall Jenner & Harry Styles Friends Now?

So, where do Harry and Kendall stand now? Well, it seems that they are still on good terms! In December 2019, Harry filled in for James Corden on The Late Late Show , where Kendall appeared as the guest. The two played a game of “Spill Your Guts or Fill Your Guts,” and Kendall did not hold back, whatsoever. “Which songs on your last album were about me?” Kendall asked the singer. “Oh God,” Harry responded to the question, burying his head in his palms. The bit was all in good fun, as the two laughed it up. But fans should know that Harry never answered the question, opting instead to chow down on some “fish’s swimmers.”

In June 2019, a source close to Harry reiterated that the two were definitely on good terms. “They are all really good friends and very cool with each other,” the insider EXCLUSIVELY told Hollywood Life . “They feel more like brother and sister and will be forever friends who will always be happy to see each other in the future.”

In November 2022, Kendall and Harry sparked reconciliation rumors when  The Kardashians  star went to the singer’s “Love On Tour” show with her BFF  Hailey Bieber and her sister Kylie Jenner . The concert was after Kendall and Harry split from Devin Booker  and  Olivia Wilde , respectively, leading fans to believe that the stars might be getting back together. However, sources clarified that Kendall and Harry are only interested in staying friends.

“Kendall will always have a special place in her heart for Harry,” one source EXCLUSIVELY told Hollywood Life . “They have always had an amazing time together and have formed a really close friendship. They’ve remained in touch over the years despite each dating other people. They have a ton of mutual respect for one another but there’s nothing going on in terms of a romance at this point.”

“They’re both newly single and it’s just not where Kendall’s head is at,” the source continued. “She loves spending time with Harry and they have a lot of fun, but things are totally platonic between them. She’s not in a position to jump into another committed relationship anytime soon.”

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A Definitive Timeline of Kendall Jenner and Harry Styles' Relationship

Kendall Jenner and Harry Styles have a lot of "History." From vacationing in the Caribbean together to spending time apart, Jenner and Styles constantly keep the public guessing as to what's really going on between them. Now, a source tells PEOPLE exclusively that the two are back on after they were spotted on a swanky dinner date in L.A. on Thursday night. To recap, here's everything we know about the on-again, off-again romance between Styles, 22, and Jenner, 20. They grabbed dinner in November 2013 The two shared a low-key dinner at Craig's restaurant in West Hollywood and were photographed leaving together in Styles' car. "They're just friends," said a source. Jenner also took a moment to tweet that she was single.

Serious rumors started flying in 2014 The stars were first linked in January 2014 when they were seen going out to dinner and hitting the slopes at Mammoth Mountain in California. (At the time, Styles was 19 and Jenner was 18.) This was the first time they acted overtly couple-y in public. "Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on," a source told PEOPLE . "Harry was a gentleman and even offered to carry Kendall's snowboard to the ski lift." Earlier this year, a source told PEOPLE that "things never got serious," despite their obvious connection.

RELATED VIDEO: See Behind-the-Scenes Moments of Kendall Jenner‘s Glam Life

In December 2015, they vacationed together in Anguilla Fans spotted them enjoying an intimate dinner together, and they were later photographed getting cozy on a yacht. The two appeared to be all smiles as they boated around the island and were even caught kissing.

A few days later, they hopped onto Ellen DeGeneres ' yacht in St. Barts, where they were again spotted looking quite couple-y.

Khloé Kardashian tried to explain her sister's relationship with the One Direction singer, saying that they were, in fact, 'dating' A few days after Styles and Jenner's New Year's getaway, Kardashian addressed their relationship status in an interview. "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 told Entertainment Tonight . But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating."

Same, Khloé. Same.

They went on a casual shopping trip in April 2016 The pair were seen shopping in Los Angeles. That January, after returning from their vacation, they had partied together at music agent Jeff Azoff's birthday celebration.

The two currently appear to be rekindling their romance On Sept. 1, 2016, Styles and Jenner were spotted on a dinner date at L.A. hot spot Tsabel, and an onlooker said that the model "was beaming" all night.

"They're rekindling their old romance and Kendall's so excited and happy about it," the source tells PEOPLE . "She's always cared for Harry."

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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.

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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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Harry Styles’ Dating History: From Taylor Swift And Kendall Jenner To Olivia Wilde and Taylor Russell

This is everything you need to know about Harry Styles' love life.

Since his split from Olivia Wilde in November 2022 — DeuxMoi reported that their relationship began to sour in the aftermath of that Don't Worry Darling drama — Styles has been celebrating his thirtieth birthday and embarking on life as a single man.

His latest rumoured partner is Bones And All star, Canadian actress Taylor Russell , who Styles has been surreptitiously spending time with in London over the course of the winter and, if the Harries are to be relieved, the pair may now even be taking things to the next stage.

Given his status as one of the world's most eligible gentlemen, it's no wonder how quickly the rumour mill has gone into overdrive with questions about Styles and Russell. Despite the Mancunian never having openly publicly dated anybody, this is everything you need to know about all of Styles' (supposed) current and past flames.

2024, Taylor Russell

According to DeuxMoi , Styles and Russell at the start of September were ‘definitely dating’ but not yet exclusive, although a source did suggest to the gossip that it’s ‘moving in that direction.’ The couple did nothing to dispel the rumours when Styles appeared at the press night of Russell’s new play The Effect at the National Theatre in London.

The pair were spotted the next day strolling along Brewer Street in London, after getting in the same car home the night before from Chiltern Firehouse.

By mid-October 2023, things had solidified between the pair. A source revealed to US Weekly that Styles 'sees a future' with Russell. 'Harry is head over heels for Taylor,' the source said. 'He loves spending as much time with her as he can.'

In February 2024, after attending the BAFTAs alone, the rumour mill went into overdrive that the pair were engaged after Russell was spotted wearing a Tiffany & Co. engagement ring - albeit on the wrong hand.

2023, Emily Ratajoswki

Four months after splitting from Wilde, Styles was seen passionately kissing model Emily Ratajkowski on the streets of Tokyo, which reportedly caused Wilde to cut off all contact with both her former flame and Ratajkowski, who was once a close friend of the actors'.

2021-2022, Olivia Wilde

The relationship that appeared to have the entertainment realm in a chokehold began in January 2021, when Styles and Wilde were first pictured together while attending his manager Jeffrey Azoff’s wedding. Their partnership is believed to have started when they worked on Don’t Worry Darling together. Fast forward a couple of months and the pair were photographed on a boat off the coast of Italy before Wilde began attending Styles’ concerts.

Despite the couple being, according to sources, ‘more serious than ever', during the summer of 2022, after the chaotic and gossip-fueled press tour for Don’t Worry Darling , things are believed to have become more strained between the pair. Then, in November 2022, a source confirmed to People that the pair were ‘taking a break’ from their relationship.

‘He's still touring and is now going abroad. She is focusing on her kids and her work in L.A.,’ a source said. ‘It's a very amicable decision.’

2017-2018, Camille Row

Styles is believed to have started dating French model Camille Row in 2017 before ending their relationship a year later, but not before using her as the inspiration behind his hit album Fine Line .

The One Direction alum confirmed to Zane Lowe that his single Cherry was not only about one of his ex-girlfriends, but also featured her voice at the end of it.

‘When we listened back to the album, I asked her to add it in,” he said. ‘I think she liked it.’

The song concludes with a voicemail in French from Rowe, which translates to: 'Hello! Are you asleep? Oh, I’m sorry…Well, no… No, it’s not important. Well… We went to the beach and now we… Perfect! Harry.'

2013-2014, Kendall Jenner

Styles and Kendall Jenner first sparked relationship rumours in 2013 following a date night at Los Angeles restaurant, Craigs. The pair shortly rang in the new year together with friends on the slopes of Mammoth, California, before spending time in the Caribbean that summer with both of their mums.

In January 2016, Jenner's elder sister Khloé Kardashian seemingly confirmed that the two were an item in some way. In an interview with Entertainment Tonight , she said: ‘They were hanging out together. Do I think they're dating? Yes. I don't know if they're, like, boyfriend-girlfriend,’ Kardashian added. ‘Nowadays, I don't know, people are weird with stuff. So I don't know their 'title’ is, but I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating.’

Jenner and Styles are believed to have gone their separate ways in early 2016 before reuniting for a short time later that year, with the Manchester native attending the supermodel's 21st birthday party in November 2016.

In an interview with Rolling Stone , Styles confirmed that his ex Jenner was a direct source of inspiration for his May 2017 debut studio album. 'She's a huge part of the album,' he said, adding, '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.'

2012-2013, Taylor Swift

The relationship that was quite possibly both of their fans’ favourites was the month-long fling between Taylor Swift and Styles, which started in December 2012 when the pair were spotted walking around Central Park together. Despite the couple breaking up after a holiday in the Caribbean in early 2013, fans are still quick to attribute the stars’ lyrics to each of their former flames. Most Swifties believe that the pop singer’s song Style is about Styles, nodding to the lyrics: I got that red lip classic thing that you like…You got that long hair, slicked back, white T-shirt.’

Naomi May is a freelance writer and editor with an emphasis on popular culture, lifestyle and politics. After graduating with a First Class Honours from City University's prestigious Journalism course, Naomi joined the Evening Standard as its Fashion and Beauty Writer, working across both the newspaper and website. She is now the Acting News Editor at ELLE UK and has written features for the likes of The Guardian, Vogue, Vice and Refinery29, among many others. 

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