Styles and Jenner Reunite at 2020 BRIT Awards: A Look at the Pairs’ Relationship Timeline

Who says a relationship has to end in heartbreak? Kendall Jenner and Harry Styles have been proving this sentiment wrong for years.

Styles is not admitting to dating rumors surrounding the pair, though the evidence shows otherwise. The 26-year-old musician skillfully dodged answering questions about him and Jenner’s past fling during a recent appearance on The Ellen DeGeneres Show, assuring DeGeneres that he and Kendall were merely “friends” for “several years.”

More recently, the supermodel and musician reunited at the 2020 BRIT Awards After-Party where attendees saw them mingling during the soiree which was held at The Standard Hotel.

As one can see, the pair has quite the relationship history.

Let’s take a look at how their “friendship” has blossomed through the years.

2013: Dining in West Hollywood

Harry Styles dines with Kendall Jenner at Craigs restaurant

Harry Styles dines with Kendall Jenner at Craig’s restaurant on Nov. 20, 2013/WENN

Styles and Jenner definitely stirred things up when they were seen together at a restaurant in WeHo following Styles split from ex Taylor Swift earlier that year. It was hard to deny dating rumors as they were photographed leaving Craig’s restaurant in Styles’ car, but they quickly denied these dating accusations. To further solidify her solitude, the then 18-year-old Jenner tweeted that she was indeed single, though she was just linked to rapper Young Jinsu the month before.

Styles on the other hand, when asked by CNN’s Piers Morgan whether or not he and Jenner were dating, was more ominous in his response, stating, “I mean, we went out for dinner, but no, I guess.”


2014: A Year of Skiing and Hangouts With Friends

Kendall And Kylie Jenner Launch New Holiday Collection At The PacSun Store on Nov. 9, 2013/FayesVision/WENN

Jenner and Styles kicked off the 2014 New Year by skiing and snowboarding in Mammouth, California. The duo reportedly stayed in a house with a group of friends, and a source told PEOPLE of the outing, “Kendall snowboarded and Harry skied. They were very cute together. There was a lot of flirting and smiling going on.” They added, “Harry was a gentleman and even offered to carry Kendall’s snowboard to the ski lift.” How adorbs!

A source also told Entertainment Tonight that, “there has been something going on with those two for a while.” According to the source, it was the Jenner “who made the first move” and invited Styles on the trip. They revealed, “Kendall doesn’t want to get hurt, so she’s proceeding with caution.” They also stated, “She knows what the deal is.”

At the end of the year, on Dec. 1, 2014, the pair further ignited dating rumors when they hung out with friend Cara Delevingne at the British Fashion Awards at the London Coliseum.


2016: The Couple Is Confirmed to Be Possibly Dating

Harry Styles at the 2014 American Music Awards

Harry Styles at the 2014 American Music Awards on Nov. 23, 2014/Kathy Hutchins/Shutterstock

Jenner and Styles chose to spend the New Year together again in 2016 by vacationing in Anguilla, in the Eastern Carribean. The “friends” were seen together at a restaurant on Dec. 29, 2016, and later seen being super friendly on a yatch. They were also joined by Ellen Degeneres and wife Portia de Rossi, as well as Kris Jenner and boyfriend Corey Gamble.

Later in the year, Kendall’s sister Khloé Kardashian spilled the beans. The Keeping Up with the Kardashians star told 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 quotations. “But I mean, they were in St. Barts together hanging out, so to me that’s dating. I would call that dating.” The status of their relationship was clearly a mystery to KoKo as she added, “I don’t know if they’ve had that talk yet.”


2019: They Met Again at the Met Gala and Reunited on The Late Late Show

Kendall Jenner at the 2019 Met Gala

Kendall Jenner at the 2019 Met Gala on May 6, 2019/Andres Otero/WENN

In May of 2019 Jenner and Styles reunited at the Met Gala. They were spotted having a conversation inside the event, and spent quite some time together that night with pals, not leaving the afterparty until 6 a.m. Around the time a source told PEOPLE that the two friends were not seeing each other, and Kendall was in fact still with her then basketball playing boyfriend, Ben Simmons. A source also told PEOPLE of Styles’ and Jenner’s relationship, “Harry was her first real relationship, so there is a lot of history there.” They added, “But they’re just friends.”

The pair of pals filled in for James Corden on The Late Late Show on Dec. 10, 2019, and did everything that exes “shouldn’t” do. They shared a meal — notwithstanding a questionable one — of scorpions, bull testicles, and salmon smoothies. Yum.

During a game of Spill Your Guts or Fill Your Guts, Jenner dished on her siblings (no pun intended) and said that Robert Kardashian is the best parent out of the bunch, but quickly stressed that all of her siblings are amazing parents. Styles was asked about his favorite solo artist out of his former One Direction comrades, but refused to answer, likely breaking the hearts of Larry Stylinson fans around the world.

At a point in the game, Jenner read a question to herself, stating “I’m dying to know this.” She proceeded to ask Styles, “Which songs on your last album were about me?” The audience amped Styles up, and he chose to eat cod sperm instead of disclose which tracks were about the supermodel.

Fans were amazed at the great chemistry between the two, and wondered if they were just really good friends post-relationship, or once again an item.

Jenner and Styles fans may be disappointed to know that Kendall recently got back together with NBA star Ben Simmons.

It’s safe to say that in the meantime, we’ll all be overanalyzing Jenner and Styles’ future interactions in hopes that the pairs’ amazing saga continues.

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