Kendall Jenner & Harry Styles: When Did They Date? Plus, Everything Else To Know

Take a walk down memory lane and look back at the relationship between Harry Styles and Kendall Jenner! Plus, learn about where the two stars stand now.

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Kendall Jenner, Harry Styles
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Kendall Jenner and Harry Styles are two of the most famous 20-somethings in the world. So, naturally, the two have crossed paths — and even been linked romantically! Rumors about the two being an item circulated in 2013, and the pair were seemingly on-and-off until 2016. All of these years later, fans still love to reminisce about those “Hendall” days, and we’ve cooked up the perfect timeline of their relationship from the early 2010s to today!

Who Is Kendall Jenner?

Kendall Jenner at the 40th Brit Awards, Sony Music After Party at The Standard in London on February 18, 2020 [Shutterstock].
Kendall Jenner rose to fame on the E! reality TV series Keeping Up With The Kardashians. She’s the eldest of two daughters shared between Kris Jenner and Caitlyn Jenner. Over the course of the series, which ended in 2021, Kendall showed a real interest in modeling. She has since become the famous face for a number of campaigns, and has walked some of the hottest runways in the world for fashion weeks! Now, Kendall is venturing into her own business pursuits, starting with her own 818 Tequila brand.

The young model has also been connected to quite a few high-profile stars when it comes to her romantic life, as well. Along with Harry, Kendall has reportedly dated A$AP RockyNick Jonas, and Ben Simmons! She has, however, made a very concise and purposeful effort to keep her romantic life out of the spotlight as much as possible.

Who Is Harry Styles?

Harry Styles poses for photographers upon arrival at the Brit Awards 2020 in London on February 18, 2020 [Shutterstock].
Harry Styles became a household name with his fellow bandmates when One Direction came onto the scene in 2010. Once the group went on hiatus, however, Harry began pursuing his solo career. He debuted his self-titled album in 2017 and followed it up in 2019 with Fine Line. In 2021, he earned his first Grammy award for Best Pop Solo Performance for his hit “Watermelon Sugar.”

Along with music, Harry has also shown a real interest and talent for acting, too. He starred in the ensemble cast of the 2017 film Dunkirk. Next, he’ll appear in the the film Don’t Worry, Darling, which is directed by his current partner Olivia Wilde. He’s currently in production for the upcoming film My Policeman.

Like Kendall, Harry has also been connected to some pretty famous figures. He memorably dated Taylor Swift in the early 2010s, and fans still believe he is the inspiration behind her song “Style.” The two are, however, on great terms now, as evidenced by their friendly meeting at the 2021 Grammy Awards. The singer has also been connected to Camilla RoweTess Ward, and Georgia Fowler, among others.

Kendall Jenner And Harry Styles’ Relationship Timeline

Harry Styles, Kendall Jenner, and Cara Delevingne at the British Fashion Awards at the London Coliseum on December 1, 2014 [Shutterstock].
Kendall and Harry seemingly first got together towards the end of 2013. The romance was, at first, fairly short-lived, and the two split in February 2014. They did, however, rekindle their romance sometime in 2015, before officially calling it quits in 2016. The two never outrightly confirmed that they were together, however, they seemed to be on good terms any time they were spotted at major industry events. In the photo above, the two were seen chatting it up with pal Cara Delevingne at the British Fashion Awards in London on December 1, 2014.

Top Moments Of Kendall & Harry Together

During their time together, Kendall and Harry definitely had a few memorable moments. One that stands atop the list for many “Hendall” shippers is totally their time canoodling on a yacht in St. Barts back in December 2015. The two definitely appeared to be super smitten with one another at the time, when their relationship was seemingly back on after going their separate ways that prior February in 2014. They were also memorably spotted in Anguilla just days prior to their St. Barts trip. Apart from their time together as a couple, they’ve also had some great run-ins post-romance. The two just happened to bump into one another at the 2019 Met Gala, where they were all smiles as they chatted and reconnected after their reported official split back in 2016.

Are Kendall & Harry Friends Now?

Harry Styles (left) poses in the press room at the 63rd annual Grammy Awards at the Los Angeles Convention Center on March 14, 2021. Kendall Jenner (right) seen out and about in Los Angeles on May 26, 2021 [Shutterstock].
So, where do Harry and Kendall stand now? Well, as far as their own personal lives go, Kendall is currently dating 24-year-old Devin Booker, who plays professional basketball for the Phoenix Suns. Harry, meanwhile, is still quietly dating his Don’t Worry, Darling director Olivia Wilde, 37. Both Kendall and Harry have made the decision to keep their romances as private as possible, especially after enduring so much public scrutiny during their time together.

When it comes to whether the two are currently friends or not, they seem to be on good terms! In December 2019, Harry filled in for James Corden on The Late Late Show, where Kendall appeared as the guest. The two played a game of “Spill Your Guts or Fill Your Guts,” and Kendall did not hold back, whatsoever. “Which songs on your last album were about me?” Kendall asked the singer. “Oh God,” Harry responded to the question, burying his head in his palms. The bit was all in good fun, as the two laughed it up. But fans should know that Harry never answered the question, opting instead to chow down on some “fish’s swimmers.”

Even in June 2019, a source close to the singer reiterated that the two were definitely on good terms. “They are all really good friends and very cool with each other,” a source close to Harry EXCLUSIVELY told HollywoodLife. “They feel more like brother and sister and will be forever friends who will always be happy to see each other in the future.”

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