Keeping up with Kendall Jenner’s love life can be tricky.
The “Kardashians” star has been romantically linked to a wide range of A-listers over the years, from singers to models.
Jenner has also dated many professional basketball players, including Phoenix Suns player Devin Booker, whom she called it quits from in October 2022.
“I think you learn different lessons in every relationship,” she said in a behind-the-scenes video from a 2020 Calvin Klein campaign.
“I think I’ve learned so many different things from so many different relationships,” Jenner continued.
Below, Page Six breaks down all of the “Keeping Up With the Kardashians” alum’s boyfriends and exes.
Harry Styles
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Jenner was spotted on a dinner date with Styles in January 2014. While the duo were believed to have called it quits soon after, they briefly sparked reconciliation rumors in December 2015 when they were photographed getting cozy aboard a yacht in Anguilla.
Although their romantic connection did not last, Jenner and the One Direction member have maintained a friendship over the years.
In November 2022, Jenner even cheered on the “Kiwi” singer at a Los Angeles concert.
While the model and Styles never officially confirmed their past romance, Kris Jenner told Ellen DeGeneres in March 2021 that “yeah,” they were an item.
Nick Jonas
When Jenner’s friend Gigi Hadid briefly dated Joe Jonas in 2015, the Hulu personality reportedly had a similarly short-lived fling with the “Cake by the Ocean” singer’s brother Nick Jonas that summer.
“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,” the insider added.
Jordan Clarkson
In March 2016, Kendall started seeing Jordan Clarkson.
She and the Cleveland Cavaliers player embarked on many high-profile dates, from Coachella to a Fourth of July bash.
The duo called it quits later that same year.
A$AP Rocky
A source confirmed to Page Six in July 2016 that Jenner was dating A$AP Rocky.
Not only did the former E! personality show her support at one of the rapper’s shows that year, but they also attended the Met Gala together.
Rocky, at the time, was photographed grabbing Jenner’s butt.
Blake Griffin
From 2017 to 2018, Jenner dated Blake Griffin — even giving Vogue rare insight into their relationship.
“I’m happy. He’s very nice,” she gushed to the magazine of the Boston Celtics player in March 2018.
Jenner and Griffin’s breakup made headlines the following month.
Ben Simmons
In May 2018, multiple sources told Page Six Jenner was dating Ben Simmons. The pair were on and off for one year before ending their relationship.
Prior to their split, she told Vogue Australia she was “maybe” considering marriage.
“Definitely not now, but maybe one day,” the 818 Tequila creator, who is the only of her siblings without a baby, said in the May 2019 interview.
Anwar Hadid
Jenner was briefly linked to Gigi’s brother, Anwar Hadid, in 2018.
She was on a break from Simmons at the time.
The longtime friends were spotted making out in July 2018, shortly after Anwar ended his relationship with Nicola Peltz.
Devin Booker
While Jenner often keeps her romances on the down-low, she did gush over Devin Booker while dating the NBA player on and off from early 2020 to October 2022.
“Him and Stormi have an amazing relationship,” she told Jimmy Fallon in September 2021, referencing her sister Kylie Jenner’s daughter. “She has the biggest crush on him, and I’m jealous sometimes. I’m like, ‘Stop. Can you guys not?’”
When the duo first broke up in June 2022, a source told Page Six that Booker’s “priority is his career” — and Jenner’s modeling similarly “dominates her life.”
However, the pair reconnected soon after, only to split again in October 2022.
“Both have incredibly busy schedules right now with their careers, and they’ve decided to make that a priority,” an insider told People at the time.
Bad Bunny
Jenner and Puerto Rican rapper Bad Bunny sparked dating rumors in February 2023 when they were spotted at the same restaurant together in LA.
The following month, the reality star and musician, who was born Benito Antonio Martínez Ocasio, made rumors swirl even further when they got cozy on a night out with Kylie.
The pair quietly hung out together — including going on a low-key horseback riding excursion — for weeks, but their romance wasn’t solidified until April when they were caught “openly kissing” at Coachella, where he performed.
The duo also attended the 2023 Met Gala and, although they didn’t walk the carpet together, hit an afterparty as a couple.
The musician and model weren’t shy about being seen in public together from that moment on, attending fashion shows, sitting courtside at basketball games and even appearing in a Gucci campaign. However, Bad Bunny refused to offer too many details about their romance in an October 2023 Vanity Fair interview.
“I’m not really interested in clarifying anything because I have no commitment to clarify anything to anyone,” he said.
Jacob Elordi
Kendall Jenner made headlines for allegedly “making out” with Jacob Elordi at a Coachella afterparty in April 2026.
The following week, reports surfaced that the pair had been seeing each other for months after being set up by Kylie.
Kendall “just clicked with Jacob,” the Daily Mail reported, noting “there was chemistry” once Kylie helped get the “Euphoria” star “out of the friend zone.”