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.
Now, following Styles’s and Jenner’s recent breakups with their respective partners, Olivia Wilde and Devin Booker, the two have reconnected and reportedly leaned on one another once again, demonstrating that their bond is still alive and well (and may even return to being something more).
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.
CBS Photo Archive//Getty Images
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.
CBS Photo Archive//Getty Images
The flirting is enough to make you blush.
View full post on Youtube
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.
Kevin Mazur/MG19//Getty Images
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.
David M. Benett
David M. Benett
