Keeping Up with the KardashiansstarKendall JennerandHarry Styleswere 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 onEllen DeGeneres' yacht and going on ski vacations for New Year’s. Jenner and Styles even enjoyed a memorable “meal” together when the formerOne Directionmember filled in forJames Cordenas host ofThe Late Late Showin December 2019. During their appearance, the two looked like old pals while playing Corden’s “Spill Your Guts or Fill Your Guts” game.
Nov. 20, 2013: Harry Styles and Kendall Jenner have a date night in West Hollywood
Harry Styles, Kendall Jenner and Model of the Year winner Cara Delevingne.David M. Benett/Getty
In 2013, following his split fromTaylor Swiftearlier 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 palCara 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
Harry Styles and Kendall Jenner.SplashNews.com
Harry Styles, Kendall Jenner, Portia de Rossi and Ellen DeGeneres.SplashNews.com
Jan. 2, 2016: Harry Styles and Kendall Jenner board Ellen DeGeneres' yacht
They continued their vacation when they boardedEllen DeGeneresand 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 saidshe thought the pair were dating, tellingEntertainment 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 toE! 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 her21st birthday bashat 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 rapperTravis Scott(though Scott would begin a relationship with Jenner’s younger sisterKylie Jennerjust 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.
Harry Styles.Isabel Infantes/PA Images/Getty
In 2017, the “Adore You” singer had fans buzzing when he seemed to allude to his relationship with Kendall in aRolling Stonearticle. 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
Kendall Jenner and Harry Styles.Kevin Mazur/MG19/Getty; Dimitrios Kambouris/Getty
It’s not uncommon for celebrities to reunite atfashion’s biggest night, but apicture was worth a thousand wordswhen 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’tendthe 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 sourcetold PEOPLEthat 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 onThe Late Late Show
Kendall Jenner and Harry Styles.Terence Patrick/CBS
Fans were sent into a tizzy when the pair hung out on camera as Stylesfilled in for CordenonThe Late Late Showand played theever-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.
Nov. 14, 2022: Kendall Jenner attends Harry Styles' concert in L.A.
For the outing, the reality star wore a plunging snakeskin halter top while her sister and Bieber sported all-black looks.
source: people.com
