The former One Direction member and model played coy about romance rumors for years until finally alluding to their past relationship during a December 2019 talk show appearance on The Late Late Show Starring James Corden. While host James Corden was out, Harry was in, and Kendall was his special guest. Naturally, the pair played “Spill Your Guts or Fill Your Guts” and The Kardashians star tried to get to get some answers out of the “Sign of the Times” crooner following their split.
“I’m dying to know this,” Kendall joked, asking Harry, “Which songs on your last album were about me?”
At the time, she was referring to his debut, self-titled record, which was released in May 2017. However, Harry refused to answer the question and instead ate whatever disgusting food was offered to him.
Romance rumors between Harry and Kendall first started swirling when they were spotted together in 2013. Throughout the years, they’ve been photographed together on multiple occasions. Fans will remember those pictures of the British star and California native on a yacht together in December 2015. It’s unclear when exactly things fizzled out between them, but eagle-eyed fans have seen them hanging out several times. In December 2018, Kendall and Harry were seen at the same Fleetwood Mac concert, they were photographed talking during the 2019 Met Gala and Kendall even supported Harry at his various concerts in 2022.
“Yeah, we’ve been friends for a while now, yeah, for, like, several years,” Harry shared on The Ellen DeGeneres Show in December 2019 when asked about their longtime friendship. “Yeah. Yeah, I think so. Right? OK!”
In November 2022, romance rumors between the two started swirling once again after Harry split with Olivia Wilde and news broke that Kendall and longtime boyfriend Devin Booker had broken up. However, things might just be friendly … for now.
“She and Harry are just good friends,” a source told E! News at the time, shutting down any possible romance speculation. “They remained friendly over the years and have kept in touch. There’s nothing romantic going on, but they do catch up from time to time and have hung out in social settings.”
Scroll through our gallery for a timeline of Harry and Kendall’s relationship and friendship timeline.
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