Kendall Jenner’s Most High-Profile Relationships Over the Years

Kendall Jenner’s dating history has often played out quietly, but her recent Super Bowl ad revived public curiosity. From musicians to NBA stars, her relationships have shaped a reputation she now openly jokes about.

Kendall Jenner sparked renewed interest in her romantic history after poking fun at her NBA exes in a Fanatics Playbook Super Bowl commercial. Rather than shy away from speculation, Jenner leaned into the joke, signaling a level of comfort with the public narrative around her dating life.

Unlike many celebrities whose relationships become tabloid chaos, Jenner has typically kept her romances quiet. Even so, her high-profile partners have ensured continued attention.

Playing Along With the Narrative

“Haven’t you heard? The internet says I’m cursed,” Jenner said in the commercial, referencing claims that basketball players struggle after dating her. While lighthearted, the moment reflected how aware she is of the online chatter.

Despite the jokes, Jenner has largely avoided oversharing, with Devin Booker being one of the few partners she acknowledged publicly on social media.

1. Harry Styles

Following Harry Styles’ 2013 breakup with Taylor Swift, he and Jenner were first spotted together in November of that year. By January 2014, they vacationed with friends on a New Year’s ski trip, where witnesses noted clear chemistry.

Two years later, they reunited in St. Barths for another New Year’s holiday. Photos showed them spending time together aboard a yacht, reigniting dating rumors.

In 2016, the pair were seen together multiple times but never confirmed a relationship. In 2019, they reunited at the Met Gala and later appeared on "The Late, Late Show." During a game segment, Jenner asked which songs on his album were about her. Styles chose to eat cod sperm rather than answer.

2. Jordan Clarkson

Jenner’s first rumored NBA relationship was with Jordan Clarkson. They were spotted together in March 2016 at California nightclubs, Coachella, and other events.

Clarkson attended Jenner’s 21st birthday in November 2016, but the relationship appeared to end shortly after.

3. Blake Griffin

Jenner and Blake Griffin were first linked in the summer of 2017. They attended concerts, social events, and group outings together, often joined by friends.

By March 2018, Jenner declined to confirm the relationship during an interview. Soon after, the pair cooled off and went their separate ways.

4. Ben Simmons

In May 2018, Jenner and Ben Simmons were seen on a lunch date at the Beverly Hills Hotel. She later confirmed the relationship during an appearance on "The Ellen DeGeneres Show" in February 2019.

They split in May 2019 but remained on friendly terms. The two were even seen together later that year around New Year’s Eve.

5. Devin Booker

Jenner was first linked to Devin Booker in April 2020 after the two were spotted on a road trip to Arizona. Their relationship became more public in 2021, with Jenner sharing photos on Instagram in February and June of that year.

They celebrated their first anniversary in June 2021. However, shortly after their second anniversary in June 2022, they split. The pair reconciled briefly and were seen vacationing together in July 2022 before quietly breaking up again that fall. Sources cited demanding schedules as the reason, noting they remained on good terms.

6. Bad Bunny

Jenner was sighted with Bad Bunny in February 2023 during a double date with Hailey and Justin Bieber at Wally’s in Beverly Hills.

7. Devin Booker (Again)

Despite previous breakups, Jenner and Booker were seen together several times between 2024 and 2025. They attended the 2024 Super Bowl separately but were both present in Las Vegas that weekend.

Additional sightings followed in Dallas, Miami, Aspen, and the last being on September 2025 in New York City.

Their playful exchange tied to the Fanatics ad reignited speculation, with fans wondering if another reunion could be possible.

Kendall Jenner’s dating history reflects her ability to balance privacy with public attention. While fans continue to speculate, she appears comfortable owning the narrative, even when it becomes a punchline. Whether single or partnered, Jenner remains firmly in control of her personal story.