A Complete Timeline of Kendall Jenner’s Dating History (2024)

Kendall Jenner has recently made headlines for her unexpected relationship with Bad Bunny, but the rest of the supermodel’s romantic history is just as buzzy.

Despite growing up as a reality star, Jenner has kept her romantic life largely under wraps, but over the last decade, she has entertained a series of passionate flings and committed relationships right at the center of the spotlight.

Here, look back at every celebrity Jenner has dated since her teens—from Harry Styles to Bad Bunny, and the NBA stars in between.

Bad Bunny (February 2023–present)

The two first connected after the Puerto Rican rapper moved to Los Angeles in February. They went officially public with their romance at this year’s Coachella Music and Arts Festival, where she was filmed by a fan getting close with the rapper in the audience during a performance, and later in the background of one of Bunny’s Instagram Stories.

The pair have been spotted on multiple outings since, including on a horseback riding date in Hidden Hills and at the NBA playoffs at Crypto.com Arena.

Devin Booker (April 2020–November 2022)

The supermodel began perhaps her most serious long-term relationship to date with the Phoenix Suns athlete in April 2020.

She was first linked to the NBA player in September 2020, when they were spotted taking a road trip together to Sedona, Arizona. By June of the following year, she had confirmed matter-of-factly to Andy Cohen that she was dating Booker. “He’s my boyfriend,” she said during the Keeping Up With the Kardashians reunion episode.

After two and a half years, their romance ultimately ended in November 2022, reportedly because of the pair’s incompatible schedules. “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. “They have a lot of love and respect for each other and wish only the best.”

Ben Simmons (July 2018–May 2019)

Jenner and the Brooklyn Nets player were rumored to be dating as early as summer 2018, but it wasn’t until Khloé Kardashian shared a video on Snapchat of the two cuddling over Fourth of July weekend of that year that their relationship was finally confirmed.

In May the following year, People confirmed that the pair had called it quits. “Their relationship ran its course,” a source told the outlet at the time.

Blake Griffin (August 2017–February 2018)

The supermodel’s ultra-private relationship with NBA star Griffin lasted just six months, but it was one marked by its share of fun outings. She and Griffin were first linked in the summer of 2017, when they were photographed leaving a Kendrick Lamar concert featuring rapper Travis Scott (who was dating Jenner’s younger sister, Kylie, at the time).

Jenner and Griffin were then spotted out on several double dates: one with Kylie and Scott at Universal Studios, and another weeks later with Hailey Bieber (then Hailey Baldwin) and Memphis Grizzlies player Chandler Parsons—the Rhode founder’s then-beau—at Craig’s restaurant in West Hollywood.

In January 2018, a source told People the pair’s relationship was “cooling off” after Griffin was spotted out in Malibu with another woman. The following month, another People insider clarified that the two were not dealing with any “particular drama,” but simply growing apart due after Griffin had been traded from the Los Angeles Clippers to the Detroit Pistons. “He got traded and isn’t local anymore, so they’ve grown apart a bit just because of distance,” the source said.

A$AP Rocky (July 2016–early 2017)

The supermodel shared a romance with the rapper that lasted nearly one year. The two were first spotted on a date in Paris in summer 2016. They were next seen at the 2017 Met Gala, where they were captured getting cozy and hanging out. (They were also captured packing on the PDA in snapshots, including one taken and shared by older sister Kim Kardashian.)

Around that time, sources confirmed the two were in a serious relationship—but things presumably fizzled out in the summer, and Jenner was linked to Griffin in August.

Jordan Clarkson (2016)

Jenner’s first NBA romance was with Los Angeles Lakers player Clarkson (who would be traded in 2018 to the Cleveland Cavaliers, becoming teammates with Khloé Kardashian's partner at the time and co-parent Tristan Thompson).

The pair first publicly confirmed their romance in April 2016, when they documented themselves on social media attending Coachella together. But the two had reportedly been dating in secret for several months before that major outing.

Following their date at Coachella, People reported that Clarkson was “really into” Jenner and that the two were “very much together and affectionate.” The previous month, an insider also told the outlet that Clarkson was “super sweet” and a “total gentleman” and “Kendall loves that.”

The pair's split was never confirmed, but Jenner was linked to A$AP Rocky later in July.

Harry Styles (January 2015–early 2016)

While in her teens, Jenner shared a puppy-love relationship with singer Harry Styles, her first major celebrity boyfriend. The pair’s relationship was officially confirmed by older sister Khloé in an exclusive interview in January 2015, but the two sparked romance rumors as early as November 2013, when they were spotted at Craig’s in West Hollywood with friend Cara Delevingne.

Jenner and Styles presumably called it quits in early 2016—around the time the supermodel reportedly began secretly dating Clarkson—but the two have remained friends, and Jenner often supports Styles at his shows. In September 2016, while Jenner was with A$AP Rocky, the exes were seen out on a platonic dinner date in Los Angeles, where Jenner was reportedly “beaming.” And in 2019, they made a joint appearance on The Late Late Show With James Corden to play “Fill Your Guts or Spill Your Guts,” where they demonstrated their lasting chemistry.