A Complete Guide to Kendall Jenner's Star-Studded Dating History

Kendall Jenner has managed to keep her romances largely low key despite growing up with cameras following her every move. The media personality became a household name at 12 years old, when Keeping Up With the Kardashians made its TV debut in 2007, and has only been thrust further into the spotlight, becoming a mainstay in the fashion world as a runway model, launching alcohol brand 818, and, overall, leading a glamorous life as a socialite. Even so, she has consistently kept her relationships under wraps, which is especially impressive considering her flames include huge pop stars and standout athletes.

According to KUWTK executive producer Farnaz Farjam, Jenner made a promise to herself of sorts when it comes to privacy. "Kendall's always had this rule: She felt like she had to be with someone for at least a year before she let them be a part of the show because she doesn't always know what people's intentions are," she said in 2021. "So that's why we kind of kept her personal life out of it, just because she had a rule."

The model elaborated on the sentiment during a May 2019 interview with Vogue Australia. "For me, a lot of things are very special and very sacred, like my friends and relationships. I personally think that bringing things into the public makes everything so much messier," she told the publication.

While Jenner has remained true to her word, her sisters have let things slip over the years. Khloé Kardashian exposed two of her baby sister's romances, while Kim Kardashian poked fun at the model by wearing a shirt emblazoned with "Kendall Starting Five" and pictures of NBA players Jenner has supposedly dated.

Whether it be through her family's loose lips or the small glimpses Jenner allows into her love life, the world has caught wind of several of her relationships over the years. Ahead, find the full breakdown of Jenner's dating history.

Harry Styles (January 2015-Early 2016)

Jenner's first major public romance was with none other than One Direction heartthrob Harry Styles. They first sparked romance rumors in November 2013 when they were seen at the restaurant Craig's in West Hollywood. Though, sources at the time claimed they were just friends.

Things ramped up by January 2014, when they spent New Year's together on a ski trip with friends. "They were very cute together. There was a lot of flirting and smiling going on," a source told People that year.

They spent New Year's together again in 2015, that time in St. Barths, where they were spotted getting cuddly on a private yacht. "There has been a lot of flirting, touching and snuggling going on. They have acted like a couple. They look very cozy and happy," an insider told People.

Days later, Jenner's older sister Khloé Kardashian spilled the beans, telling Entertainment Tonight, "They were hanging out together. Do I think they're dating? Yes. 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.' But I mean, they were in St. Barts together hanging out, so to me that's dating. I would call that dating."

The pair continued to spend time together, but by September 2016, People reported they were "not officially back together [but were] continuing to talk and see where things go." The "Watermelon Sugar" singer did, however, attend Jenner's birthday bash in November of that year.

The old flames reunited at the 2019 Met Gala and again in December of that year, when they appeared on The Late, Late Show together. While playing "Spill Your Guts or Fill Your Guts," Jenner asked the hitmaker which songs on his last album were about her, to which he responded by eating cod sperm to avoid answering. All in all, the two seemed to enjoy each other's company. "Harry was her first real relationship, so there is a lot of history there, but they're just friends," a source told People.

Jordan Clarkson (2016)

The model became a WAG for the first time when she coupled up with NBA player Jordan Clarkson. They were first spotted together in March 2016. They continued to hang out, partying at Coachella a several Hollywood nightclubs, and officially confirmed their romance in April 2016.

"They keep things low-key when they're in public, but in private they're very much together and affectionate. He's really into her," a source told People at the time.

However, in June of that year, an insider told People, "He's become really close friends with her group and they're still seeing each other, but it's not a serious situation. Jordan's been seeing other girls too."

Clarkson was spotted at Jenner's 21st birthday in November 2016 and also attended Drake's American Music Awards afterparty together, however, their romance fizzled out shortly after.

A$AP Rocky (July 2016-early 2017)

Although the star pair never officially confirmed their relationship, they were romantically linked for nearly a year. Jenner and the rapper were first spotted together in June 2016, sharing a meal at one of her favorite restaurants L'Avenue in Paris. In October of that year, they were captured arriving at a hotel together in Los Angeles and that December, they enjoyed a trip to Art Basel in Miami.

In April 2017, Jenner supported Rocky at his Coachella performance, and onlookers told People they were "all over each other" at an afterparty. The next month, they were all smiles at the Met Gala, however, they were narrowly seen together following the event.

Blake Griffin (August 2017-February 2018)

The 818 Tequila founder once again went from a musician to an athlete when she started dating NBA player Blake Griffin. They first became romantically linked in the summer of 2017, when they were spotted at a Kendrick Lamar concert that featured Travis Scott, who was dating Jenner's sister, Kylie, at the time. They followed up on their music date with several double dates, including at Universal Studios with Scoot and Kylie once again, as well as at Craig's with Hailey Baldwin (now Bieber) and her then-boyfriend Chandler Parsons of the Memphis Grizzlies.

In January 2018, Griffin was spotted out in Malibu with another woman, which sparked feverish interest in the state of their relationship. A source told People at the time that their romance was "cooling off." A month later, another source told the publication the two weren't dealing with "particular drama" but were growing apart as Griffin was traded from the Los Angeles Clippers to the Detroit Pistons.

Ben Simmons (July 2018-May 2019)

The model and the NBA player were first seen together in May 2018 enjoying a lunch date at the Beverly Hills Hotel. However, their relationship went unconfirmed for a few months until Khloé Kardashian, once again, exposed her sister's love life by posting a video to Snapchat, in which Jenner and Simmons are seen cuddling during Fourth of July weekend. Jenner herself went public about their coupling for the first time in February 2019 on The Ellen DeGeneres Show.

The host asked, "So obviously you're dating this guy who's on the 76ers. How long have you been dating him?" To which, Jenner smiled wide and said, "For a bit now."

However, by May 2019, the couple called it quits. "The relationship ran its course. She's spending time with her friends and back to being in fun mode," a source told People.

Despite their split, there was no bad blood between the old flames. They were even spotted spending New Year's Eve together that same year.

Devin Booker (April 2020-November 2022)

Jenner began her serious relationship with the Phoenix Suns guard in April 2020, when they were spotted on a road trip to Sedona, Arizona, together. The following September, they enjoyed another getaway, this time to a lake house with Justin and Hailey Bieber. She made an exception to her rule about keeping her relationships low key, when she and Booker went Instagram official in February 2021 for Valentine's Day. They both posted sweet snaps of the other to their Stories.

In June 2021, the pair celebrated their one-year anniversary with more PDA-packed Instagram photos. The same month, Jenner told Andy Cohen, "He's my boyfriend" of Booker during the Keeping Up With the Kardashians reunion. "She is crazy about him," a source told People at the time. "She has never looked happier. Her whole family loves Devin too."

After commemorating two years together, Jenner and Booker briefly split. However, by July 2022, they appeared to rekindle things, as Jenner shared Booker's NBA 2K23 cover to Instagram and they went on a tropical vacation. In September of that year, they looked smitten at the U.S. Open.

However, all good things come to an end, as the pair quietly broke up in October 2022. "Both have incredibly busy schedules right now with their careers and they've decided to make that a priority," a source told People at the time.

Bad Bunny (February 2023-present)

Following Bad Bunny's move to Los Angeles in February 2023, he and Jenner were spotted leaving a restaurant together, where they reportedly shared a meal with the Biebers. Shortly after, People reported the pair were spending time together after being introduced through friends. An insider added, "She likes him and is having fun. He is different from guys that she dated in the past. He is very charming."

In March 2023, the rapper seemingly dissed Jenner's ex-boyfriend Booker on his track "Coco Chanel" with the lyrics, "sun in Puerto Rico is hotter than in Phoenix" and "she knows it," reportedly referencing Booker's basketball team the Phoenix Suns. Booker responded in a since-deleted Instagram comment, saying, "He worried about another MAN again."

The next month, the pair was spotted packing on the PDA at Coachella and taking a romantic horseback ride on Jenner's horse, Arizona. Weeks after that, they had their first public date sitting court side at the NBA playoff match between the Los Angeles Lakers and the Golden State Warriors. In October 2023, they were captured getting cozy at a Saturday Night Live afterparty, following Bad Bunny's appearance as both host and musical guest.

In December 2023, a source confirmed to People that the pair had split, however, reconciliation rumors swirled in May 2024 after Jenner was seen attending Bad Bunny's Orlando Concert. A week later, they were seen at a Met Gala afterparty.

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