Kendall Jenner’s Romantic History: From Her Exes to Off-and-On Romance With Devin Booker

After her breakup with Bad Bunny, Kendall Jenner reportedly starting seeing Devin Booker again. Look back at all of her relationships and rumored flings.

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kendall jenner
Image Credit: Steve Sands/NewYorkNewswire/Bauer-Griffin/Shutterstock

Kendall Jenner has been in the public eye for most of her life, so it comes as no surprise that the Keeping Up With The Kardashians alum has romanced a few high-profile men over the years. From her on-and-off relationship with former One Direction heartthrob Harry Styles, to her off-and-on relationship with Devin Booker, we’re looking back at all of the lucky men who have dated the reality star turned supermodel.

Nick Jonas

Nick Jonas
Nick Jonas and Kendall Jenner had a brief fling. Image: KCS Presse / MEGA

Former Disney Channel star Nick Jonas was linked to the supermodel back in 2015 when his older brother Joe Jonas was dating Kendall’s pal Gigi Hadid. It was reported at the time that Gigi set up the pair, however the Jonas Brothers star denied the claims. “We’re not dating. Kendall is great, and naturally, with her being good friends with Gigi and with Joe and Gigi dating, there are times we’ll be in the same place and we all hang out,” Nick told E!

Harry Styles

harry styled
Harry Styles and Kendall Jenner. Image: NGRE / BACKGRID

Kendall and Harry Styles were first linked when they were spotted having dinner together in Los Angeles in November 2013. It was reported that the pair split a few months later in early 2014, however they rekindled their romance the following year. They were spotted spending New Years together, canoodling on a yacht while on vacation, and Kendall’s big sis Khloe Kardashian seemingly confirmed the romance. “Do I think they’re dating? Yes,” she told Entertainment Weekly. “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.” The public didn’t see much from them until they were spotted shopping together in April 2016, however they split later that year. It seems the pair ended on good terms, as they appeared on James Corden‘s The Late Late Show together in 2019.

Jordan Clarkson

Jordan Clarkson and Kendall Jenner. Image: Terma / SL / BACKGRID

Kendall began casually dating NBA player Jordan Clarkson in July 2016. They hung out sporadically throughout the year, with an eyewitness report in E! claiming the pair were cozying up to each other at Drake’s 2016 American Music Awards after-party. “She was laughing the whole time! She was super giddy and loving every minute of it. It was obvious that they have a very playful, fun relationship,” the source told the outlet. “They were extremely affectionate and sweet towards one another. It’s obvious he makes her so happy!” Nevertheless, they split sometime in 2016.

A$AP Rocky

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Kendall Jenner steps out with A$AP Rocky. Image: Jean-Marc Haedrich/SIPA

Kendall and A$AP Rocky sparked romance rumors when they attended Kanye West’s Yeezy fashion show together in August 2016, and were later spotted together at the 2017 Met Gala. Despite being romantically linked for over a year, the supermodel and the musician never made things official. “Kendall and ASAP weren’t seeing each other a lot,” an Us Weekly source said in September 2017. “They weren’t really official but were obviously dating. Their schedules are really hard.”

Blake Griffin

Blake Griffin and Kendall Jenner. Image: Lies Angeles / MEGA

Kendall reportedly began dating NBA star Blake Griffin in August 2017. Although their romance was brief, she opened up about their relationship in a March 2018 Vogue interview. “I’m happy. He’s very nice,” she said. “I have someone being very nice to me.” The two were spotted out and about together for around seven months before calling it quits in April 2018.

Ben Simmons

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Kendall Jenner and Ben Simmons. Image: MEGA

Kendall began dating Australian born basketball player Ben Simmons in July 2018. She had an on again, off again relationship with the Philadelphia 76ers star for nearly two years, breaking up for the first time in May 2019 before rekindling their relationship. She actually confirmed that they dated on a February 2019 episode of The Ellen DeGeneres Show, saying she dated the athlete “for a bit”. Things began heating up again in early 2020 when she spent time with his parents during and after a Feb. 11 Sixers game in Philadelphia. In a pic posted to Instagram, Kenny was all smiles walking with the NBA star and his parents following the 76ers beating the L.A. Clippers. The appeared to call it quits shortly afterward as the coronavirus pandemic began.

Devin Booker

Kendall Jenner and Devin Booker. Image: BACKGRID

Kendall and her latest fling Devin Booker were a fan-favorite 2020 quarantine couple. The stylish duo were first spotted on a road trip in Arizona that year. The Phoenix Suns point guard even took his romance with Kendall interstate, visiting pals Justin Bieber and Hailey Baldwin in Idaho on September 3.

The pair dated on and off for two years until they briefly split in early 2022. Though they apparently had a happy reunion at the time, they eventually called it quits again later that year.

Following her breakup from Bad Bunny, TMZ reported in February 2024 that Kendall started seeing Devin again, but the two were “taking things slow.”

Bad Bunny

Months after splitting from Devin, Kendall was photographed kissing rapper Bad Bunny in early 2023. Though they have not publicly commented on their romance, they graced the front row of Gucci’s fashion show during Milan Fashion Week in September of that year. Once their relationship is out in the open, the reality TV star and the “MONACO” artist were spotted spending time together several times. However, their romance came to an end by the end of 2023, as multiple outlets reported that they split.

At the start of 2024, though, Bad Bunny and Kendall reportedly took a trip to Barbados with a group of mutual friends.

Bad Bunny
Szilveszter Makó/Vanity Fair)