Harry Styles & Kendall Jenner Relationship Timeline

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Harry Styles’ relationship with Kendall Jenner has gotten renewed interest after the duo appeared on The Late Late Show. Jenner asked the pop star if he had written any songs about her in the past, but Styles refused to answer her. Did Styles and Jenner ever date? Are they still romantically involved? Read on for a full timeline of their relationship.

Styles and Jenner were first spotted together in 2013. They went on a dinner date at Craig’s Restaurant in West Hollywood, and they were photographed leaving the restaurant together in Styles’ vehicle. Jenner got on Twitter and debunked the dating rumors once the photos went viral. “Enough with the rumors,” she wrote. “I’m single, people.” Styles also addressed the rumors during a CNN interview, but he was less definitive. When asked if he and Jenner were an item, he replied, “I mean, we went out for dinner, but no, I guess.”

Styles & Jenner Have Been Romantically Linked Since Their 2013 Dinner Date

Styles and Jenner then took a ski trip together in January 2014. They refused to comment on the trip, but an inside source told People that they were being flirtatious with each other. “Kendall snowboarded and Harry skied,” the source claimed. “They were very cute together. There was a lot of flirting and smiling going on. Harry was a gentleman and even offered to carry Kendall’s snowboard to the ski lift.”

The pair took another trip to Anguilla in December 2015. A source told Entertainment Tonight that both Styles and Jenner were interested in a romance, but the latter wanted to take things slow/ “There has been something going on with those two for a while, [but] Kendall doesn’t want to get hurt, so she’s proceeding with caution,” the source explained. “She knows what the deal is.”

Khloe Kardashian Claimed That They Were Dating In 2016

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Khloe Kardashian told ET that she thought her sister and Styles were an item. “Do I think they’re dating? Yes,” she admitted. 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. But I mean, they were in St. Barts together hanging out, so to me that’s dating.”

The last flicker of Styles and Jenner’s potential romance continued happened in September 2016. They were seen getting dinner together at Ysabel in Los Angeles, where an onlooker said that Jenner “was beaming” all night. The trail of their relationship went cold after that, and the next time fans heard about Styles and Jenner was when the former was promoting his debut album in 2017.

Jenner Inspired Several of the Tracks on Styles’ Self-Titled Album


Spill Your Guts: Harry Styles & Kendall JennerLate Late Show guest host Harry Styles challenges Kendall Jenner to a game of Spill Your Guts or Fill Your Guts, in which the two ask each other very personal questions and face a choice: answer truthfully or eat whatever is in front of you. Will cod sperm and a salmon smoothie force them to…2019-12-11T07:08:34.000Z

Styles told Rolling Stone that an old flame inspired several of the tracks on the album, but he refused to mention her by name. “She’s a huge part of the album,” he said. “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.” The recent Late Late Show interaction between Styles and Jenner seems to add weight to the theory that Jenner was the woman he sang about.

The last public sighting for Styles and Jenner was at the 2019 Met Gala. The pair were seen chatting and being friendly at the event, and even left around the same time. Mirror Online claimed that Jenner and Styles were “two of the last people to leave” and they were “relaxed and happy in each other’s company.”

Only time will tell if Jenner inspired Styles’ songwriting on his latest album Fine Line, or if the rumored exes will rekindle their romance.