“No story, we’re friends,” Kendall Jenner told E!’s Giuliana Rancic in November 2013 when asked about her relationship status with Harry Styles after they were spotted dining together in West Hollywood. “He’s cool.”
However, subsequent sightings of the pair in New York and London even had Brody Jenner speculating on their dynamic. “I’m sure she’s having a fun time with him,” he told the New York Daily News that December. “She has a very level head, great head on her shoulders. But they are both so young.”
At the time, Kendall was 18 and Harry 20. Despite their young age, they never lost each other’s numbers and reunited for several outings in 2016. During a photo shoot with Australian Vogue in spring 2019, Kendall streamed a 76ers game and FaceTimed the Melbourne native to show him her copy of his recent GQ Australia cover.
“For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier,” Kendall told Australian Vogue. “Also, I’m very young, and right now I feel like relationships aren’t always super-certain.”
By the first Monday in May 2019—coinciding with the Met Gala—they had amicably split. Kendall anticipated that her packed schedule could pose too many complications. As she reflected to Australian Vogue, “Everyone has their own path and their own way of letting the cards fall. Your 20s are for messing up and figuring it out.”
Meanwhile, fans began to notice a pattern. In 2019, a fan tweeted a meme titled “Starting 5 of NBA Players Kendall Jenner Dated,” showcasing photos of Jordan Clarkson, Ben Simmons, Blake Griffin, then-Laker Kyle Kuzma, and journeyman D’Angelo Russell. “This is a playoff team lmao,” the fan wrote.
Kendall quickly responded by reposting the meme with a clever comment: “2 out of 5 accurate, thanks.”
Kendall’s NBA dating streak continued when she began dating Phoenix Suns shooting guard Devin Booker in 2020. The couple remained together for almost two years and even attended sister Kourtney Kardashian’s Italian wedding in May 2022 as a pair.
However, by June 2022, they were taking time apart. A source told E! News, “After they got back from their trip, they started to feel like they weren’t aligned and realized they have very different lifestyles.”
They briefly rekindled things that July, but by November 2022, their busy schedules once again led them to go their separate ways. Meanwhile, Devin Booker had by then bumped D’Angelo Russell out of “Kendall’s Starting Five,” just as Kim Kardashian got her hands on a T-shirt version of the meme.
Fast forward to Valentine’s Day weekend 2025, when the pair were spotted sitting side-by-side at an Aspen restaurant, sporting snow goggles. This moment was a reminder that one’s 20s really are about letting things happen and figuring it out.
In 2023, Bad Bunny entered Kendall’s life. They were first spotted in February during an apparent double date with Justin and Hailey Bieber. Kendall then caught the Puerto Rican artist’s set at Coachella in April. The following month, they attended a Met Gala afterparty together and matched outfits at a Lakers game.
Numerous date nights followed, and they sat side by side at the Gucci show during Milan Fashion Week in September. However, by the end of the year, they were no longer a couple.
That said, because “if you can stay friends, then why not,” the duo—who share mutual friends—have reunited many times since, all over the world. Demonstrating the strength of their friendship, Bad Bunny was even in the audience to watch Kendall walk for Calvin Klein Collection’s Autumn/Winter 2025 show during New York Fashion Week in February.
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