From Flames to Old Pals? Breaking Down Harry Styles' and Kendall Jenner's Relationship History

Kendall Jenner and Harry Styles looked like old pals when Styles filled in for James Corden on The Late Late Show on Dec. 10. The exes even shared a meal together. Albeit a meal of bull testicles and salmon smoothies over deeply personal questions about her siblings (Jenner said Rob Kardashian is the best parent out of the bunch) and favorite solo artist out of their bandmates (Harry ate a water scorpion rather than reveal his preference), but still it was a meal!

If the chemistry between the two had you like …

You’re not alone! The pair share quite the relationship history that includes trips on Ellen Degeneres‘ yacht and New Year’s ski vacations. Here’s everything you need to know about Jenner and Styles’ relationship through the years.

A 2013 Date Night in WeHo

David M. Benett/Getty
David M. Benett/Getty

In 2013, following his split from Taylor Swift earlier in the year, the pair shared a 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.

They Hit the Slopes in 2014

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!

Ringing in 2016 on Ellen DeGeneres’ Yacht

Styles and Jenner rang 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.”

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.”

‘Rekindling Their Old Romance’ in 2016

A source told PEOPLE exclusively in September 2016 that, after getting cozy over the holidays, the pair were back on, and that Jenner was “so excited and happy about it.” They added, “She’s always cared about Harry.” Styles and Jenner were spotted on a date in L.A. in September, with an onlooker saying that Jenner was “beaming all night.”

Gotta love when big sisters blow up your spot! Khloé Kardashian confirmed that 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.”

Harry’s Rolling Stone Revelation in 2017

Isabel Infantes/PA Images/Getty
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 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?

A Met Gala Reunion in 2019


Kevin Mazur/MG19/Getty; Dimitrios Kambouris/Getty
Kevin Mazur/MG19/Getty; Dimitrios Kambouris/Getty

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 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.”

A Late, Late Reunion in December 2019

Terence Patrick/CBS
Terence Patrick/CBS

Fans were sent into a tizzy when the pair hung out on camera as Styles filled in for James 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 model and TV personality.

Terence Patrick/CBS
Terence Patrick/CBS

Guess we’ll just have to wait and see if these two decide to go on a less disgusting dinner date!