Did Kendall Jenner and Harry Styles Date? From 2013 to 2019, numerous reports connected the Keeping Up with Kardashians star and One Direction singer romantically. Although they never revealed their relationship status publicly, these two had quite a history together – from venturing aboard Ellen DeGeneres’ boat to skiing during New Year’s Eve celebrations!
When Harry Styles stepped into the shoes of James Corden as host of The Late Late Show in December 2019, he and Kendall Jenner showed how close they had become with their shared appearance on “Spill Your Guts or Fill Your Guts”. But just how long have these two been seeing each other? From that first date to when they spilt all the beans about themselves during late-night TV, let’s look back at their relationship.
When Did Kendall Jenner Date Harry Styles?
In 2013, after being introduced by their respective managers, Kendall and Harry were first seen kissing. Reconciliation rumours surfaced two years later after they were spotted together on a yacht in Anguilla.
Kendall & Harry Styles’ Relationship Timeline
2013
This past year, after the break-up between Taylor Swift and him, Styles was seen leaving Craig’s restaurant in West Hollywood with his car. Both parties quickly rejected any insinuations of a romantic relationship that may have come out of this meeting.
A source close to the situation revealed to PEOPLE that Kendall and I were just friends. However, this didn’t stop rumours from sprouting up when they attended the British Fashion Awards on December 1st alongside mutual friend Cara Delevingne. To end any gossip, Kendall tweeted out her gladness at being single.
2014
On New Year’s Day 2014, Styles and Jenner made a splash when they were seen snowboarding in Mammoth, California. The two appeared to be travelling together as part of a larger group, yet after the trip, an onlooker informed PEOPLE magazine that “Harry went skiing & Kendall rode a snowboard”. These two had their winter activities planned out accordingly!
It was clear to everyone: Harry and Kendall were a perfect match. They exchanged knowing glances and shared countless smiles throughout the evening. What made this scene even more delightful? People noticed how polite Harry was, offering to carry Kendall’s snowboard to the ski lift! And let’s not forget about that stunning winter scenery – breathtaking!
2015
On the first day of 2014, Styles and Jenner were spotted enjoying a winter holiday in Mammoth, California. They certainly looked like an item when they shared a rental house with others. An eyewitness even reported to PEOPLE after the break that Kendall zipped down snowboard slopes while Harry zoomed around on skis!
Vividly, it was a sight to behold—they were utterly precious together. Winks and grins filled the air while onlookers praised Harry’s gentlemanly behaviour, noticing he had offered to carry Kendall’s snowboard up to the ski lift! Amidst stunning wintery backdrops, they shared an unforgettable experience.
2019
At the 2019 Met Gala, Kendall and Harry’s reunion sent a solid message to all onlookers. Despite one insider reporting that they were not dating and that she was still with her ex-boyfriend Ben Simmons, their evening extended beyond the night of fashion’s biggest event. Although there is much history between them, our source confirmed “Harry was her first serious relationship,” but ultimately, they are just friends despite what happened between them in the past.
Who Is Kendall Jenner Dating Now?
When Devin Booker and Kendall Jenner were seen together outside a rest stop in Sedona, Arizona, at the start of 2020, speculation started to spread. Eventually, they confessed that their relationship was more than platonic–and it has been an on-again/off-again situation since then.
Who Is Harry Styles Dating?
Rumours have been swirling that Olivia Wilde and Harry Styles began dating in early 2021, which was later confirmed valid. Following their collaboration on Don’t Worry Darling, a connection between them blossomed into romance. However, despite her newfound relationship with Harry, Olivia is embroiled in a contentious custody battle alongside former partner Jason Sudeikis following their recent split. Furthermore, it has recently been confirmed that Kendall Jenner’s rumoured relationship with Devin Booker is legitimate too!