Kendall Jenner and Harry Styles’s Complete Romantic History

The Kendall Jenner and Harry Styles relationship of the 2010s was a flash in the pan, but in the years afterwards, the two have remained close friends or perhaps continued to be secret lovers.

Young Kendall and Harry Styles at the beginning of their relationship. Getty Images

Jenner served as the singer’s frequent inspiration and one of her earliest committed relationships, while Styles was the supermodel’s lovely musical lover throughout her late adolescent years. Around the end of 2013, the two started dating; however, a few years later, they decided to peacefully break their relationship.

The model and singer had a long-standing love history, which included excursions on Ellen DeGeneres’ yacht and New Year’s ski getaways, even though they never publicly acknowledged their relationship. Even when Styles took over for James Corden as host of The Late Late Show in December 2019, Jenner and the former member of One Direction shared a memorable “lunch.” While playing Corden’s “Spill Your Guts or Fill Your Guts” game, the two appeared as though they were longtime friends.

Now that Styles and Jenner have reconciled and apparently leant on one another after their separate breakups with companions Olivia Wilde and Devin Booker, it is clear that their friendship is still strong (and may even return to being something more).

Check out the supermodel and singer’s youthful romance below, and stay tuned for updates on any prospective reconciliation.

Jenner attends Styles’ concert on November 14, 2022.

Jenner is shown dancing to the singer’s music on the stands alongside sister Kylie Jenner and best friend Hailey Bieber while cheering on Styles in Los Angeles.

On social media, videos posted by fans appear to show Styles blowing Kendall Jenner a kiss while he performs “Love of My Life,” which is said to be about her.

They appear together on The Late Late Show on December 10, 2019.

On The Late Late Show with James Corden, the ex-couples make a combined appearance and play the game Fill Your Guts or Spill Your Guts to showcase their natural, enduring connection.

According to the rules of the game, the two interrogate one another with a series of difficult questions, such as which songs from Styles’s 2017 album were explicitly about Jenner. They must either honestly respond to the questions or pass to try a variety of unappealing items.

CBS PHOTO ARCHIVE//GETTY IMAGES

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

KEVIN MAZUR/MG19//GETTY IMAGES

Throughout the annual fashion show, the two get along well with one another. The next morning around 6 a.m., the two are reportedly seen leaving an after-party with pals. Though an insider with People claims that the two are still not dating, their public reunion has sparked whispers of a possible revived romance. The insider said at the time, “But they’re just friends. Harry was her first genuine romance, so there is a lot of history there.

Styles reveals Jenner as his muse on April 18, 2017.

ISABEL INFANTES/PA IMAGES/GETTY

The singer admits that his now-ex Jenner was a major inspiration for his May 2017 first studio album in a Rolling Stone article. He tells the magazine, “She’s a huge part of the album” adding that “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.”

Styles celebrates Jenner’s 21st birthday on November 2, 2016.

Jordan Clarkson, Jenner’s other supposed ex, was also present at the star-studded birthday celebration held at Delilah in Los Angeles where the singer was photographed.

They go out to dinner as friends on September 1st, 2016

Styles and Jenner, who split up earlier this year, were seen out together again for a dinner date in Los Angeles. Jenner is said to be “beaming all night.” A source subsequently tells People that they are “not officially back together” and are simply continuing to communicate and see where things go, despite the reports that the two may be rekindling their romance following their outing.

While Jenner is “hopeful” about rekindling a connection with Styles, the insider continues, she is also acting more cautiously.

They ring in their second New Year’s together from December 29, 2015, to January 2, 2016.

During their Caribbean vacation, the two are seen getting cozy on several yachts.

“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.”

On January 7, Jenner’s older sister KhloĂ© Kardashian appears to confirm that the two are romantically together. She admits that she believes that Jenner and Styles are dating in an exclusive interview with Entertainment Tonight, but she is unsure as to whether the two have really had “the 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.”

They bond on the slopes on January 1, 2014.

In Mammoth, California, where they go skiing with pals to welcome in the new year, Jenner and Styles are said to spend a lot of one-on-one time together. However, observers claim that there is an obvious attraction between the two even if they are not yet formally dating. “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.”

On November 20, 2013, they initially ignite speculations of a romance.

An 18-year-old Jenner and a 19-year-old Styles are pictured in the singer’s car after a date night at Craig’s restaurant in West Hollywood for their first ever documented night out. After the meal, the first relationship rumors start to circulate, but Jenner subsequently clarifies on Twitter that she is, in fact, still single. A People source at the time further stated, “They’re simply buddies.”

Harry Styles, Kendall Jenner and Cara Delevingne at the London Coliseum. DAVID M. BENETT/GETTY IMAGES

However, on December 1, 2014, they are once more seen together with Cara Delevingne at the British Fashion Awards, which were hosted at the London Coliseum, a few weeks later.

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