“I think you learn different lessons in every relationship,” the model said in a behind-the-scenes video for her Calvin Klein campaign in February 2020. “So I think I’ve learned so many different things from so many different relationships.”
She added: “A lot of the relationships have taught me more about myself, which is the most valuable. And like, what I want from a person or from a relationship.”
The Kendall + Kylie cofounder’s first public romance was with Styles, to whom she was linked in 2013 before sparking reconciliation rumors two years later on a trip to Anguilla with the former One Direction singer.
Despite going their separate ways, the pair have remained close — which Jenner has done with more than one of her exes.
“Harry and Kendall are great friends and always have been,” a source exclusively told Us Weekly in December 2019. “It’s an easy, super chill friendship.”
While the reality star rarely speaks out about her personal life, she has clapped back at haters who’ve wrongfully commented on her dating past.
“This is a playoff team lmao,” a social media user wrote in July 2019 alongside an image titled “Starting 5 of NBA Players Kendall Jenner Dated,” insinuating Jenner’s been linked to an entire starting lineup.
The five athletes in the meme were D’Angelo Russell, Jordan Clarkson, Simmons, Kyle Kuzma and Blake Griffin.
“2 out of 5 accurate, thanks,” Jenner fired back, referencing her relationships with Simmons (whom she dated on and off from May 2018 to May 2019) and Griffin (whom she romanced from September 2017 to March 2018).
“Nba players passing around Kendall Jenner,” a social media user captioned a video of three men playfully tossing a little girl in a circle. A second user replied, “Maybe she passing them around.”
The E! personality shot back: “They act like I’m not in full control of where I throw my cooch!”
Scroll down to take a look back at the model’s star-studded romances through the years:
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Jenner and the former One Direction member were first linked in January 2014 after they had dinner together and went skiing at Mammoth Mountain in California. They were spotted getting cozy and kissing once more in December 2015 aboard yachts in Anguilla and St. Bart’s. Though their romance didn’t last long, the pair have maintained a close friendship: Jenner even cheered on Styles in the audience at one of his concerts at The Forum in Inglewood, California, in July 2018.
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The Keeping Up With the Kardashians star and the “Jealous” crooner had a brief fling in the summer of 2015 after being set up by her friend Gigi Hadid and his brother Joe Jonas, who were dating at the time. “Nick was single and looking to date, and there was an obvious attraction,” a source told Us Weekly at the time. “He absolutely thinks she’s hot.”
Credit: Gilbert Carrasquillo/FilmMagic; Michael Loccisano/Getty Images
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Jenner started dating the Cleveland Cavaliers point guard in March 2016. They attended the Coachella Valley Music and Arts Festival together the following month and later celebrated the Fourth of July at a party in Malibu. However, their romance fizzled out soon after.
Credit: Noel Vasquez/Getty Images; Robert Laberge/Getty Images
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The reality star started hanging out with the “F--kin’ Problems” rapper in late July 2016. They attended a Coachella party in April 2017, and an eyewitness told Us that the couple “were super cozy and super close.” The next month, Jenner and Rocky attended the Met Gala together, where they again showed plenty of PDA. By September 2017, a source told Us that the two “weren’t really official, but were obviously dating” despite their busy schedules.
Credit: Pierre Suu/GC Images
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Jenner and the Detroit Pistons point guard began hooking up in September 2017. A source close to the model told Us a month later that the duo made their relationship official and became a “full-on couple.” She sat courtside at several of his basketball games and even supported him at one of his comedy shows. Jenner told Vogue in March 2018, “I’m happy. He’s very nice.” They broke up later that month.
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The E! personality started seeing the Philadelphia 76ers point guard in May 2018 after his brief relationship with singer Tinashe. An insider told Us in July that the couple were “dating and exclusive, though not ‘official.’” That said, they rented a $25,000-a-month home in West Hollywood for the summer. They also traveled to Puerto Vallarta, Mexico, together with her sister Khloé Kardashian and Tristan Thompson. However, a source confirmed to Us in September that the summer fling came to an end. They reconnected shortly after, however, and an insider told Us in November that “they’re still having fun and hooking up.” The couple ended their romance again in May 2019.
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Us confirmed in June 2020 that the reality star and the Phoenix Suns basketball player were “hooking up” casually after sparking romance rumors in April while taking a road trip to Sedona, Arizona. A second source told Us in October 2020 that the pair “are still seeing each other, but it’s not super serious.” Jenner and Booker made their relationship IG official on Valentine's Day in February 2021.
While things appeared to be getting serious for the pair as he attended Kourtney Kardashian and Travis Barker’s wedding in May 2022, the nuptials “put things into perspective” for the pair and they called it quits, per insiders.
According to one source, the duo are hoping to “figure out if a future together is what’s meant to be” as they “take this time to focus on themselves" as they broke up in June 2022. They were back together by the following August.
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