Kendall Jenner Trolls Athlete Exes in Kardashian Curse Super Bowl Ad

Harry Styles

"No story, we're friends," Kendall Jenner told E!'s Giuiliana Rancic in November 2013 of her and Harry Styles' relationship status after they were spotted at dinner in West Hollywood. "He's cool."

But subsequent sightings in New York and London even had Brody Jenner guessing that, whatever was up between them, his half-sister was in the driver's seat.

"I'm sure she's having a fun time with him," he told the New York Daily News that December. "She has a very level head, great head on her shoulders. But they are both so young."

Then 18 and 20, Kendall and Harry never lost each other's numbers, reuniting for stop-the-presses outings in 2016 (including a PDA-packed stay aboard a yacht), 2018, 2020...

So, at the very least, a lasting friendship was in the cards for the duo, who sparked romance rumors again as recently as 2022, following Harry's split from Olivia Wilde.

"She and Harry are just good friends," a source told E! News at the time. "They remained friendly over the years and have kept in touch."

Justin Bieber

Kendall never dated Justin Bieber, but they were around each other enough that some people speculated they were.

Enough so that it was brought up during a Nightline interview Kendall gave in 2014.

"He's a longtime friend of our family," she said of the "Baby" singer. "Everybody loves to assume things, but no."

Moreover, Kendall has been besties with Hailey Bieber for ages, and she's been known to double date with the married couple when she has a plus-one in her life, or just chill with the duo on her own.

Nick Jonas

In August 2015, freshly single Nick Jonas was rumored to be seeing Kendall after being introduced into her orbit by brother Joe Jonas and his then-girlfriend Gigi Hadid.

But they weren't on the level of dating, according to Nick.

"Kendall is great," he told E! News at the time, "and naturally with her being good friends with Gigi and with Joe and Gigi dating, there are times we'll be in the same place and we all hang out."

Jordan Clarkson

There were rumored fireworks between Jordan Clarkson, then playing for the Los Angeles Lakers, and Kendall over Fourth of July in 2016—and they seemed to still be getting along swimmingly in November, once basketball season was underway. 

Jordan was also a guest at Kendall's star-studded 21st birthday party that month, but their connection remained in the casual zone.

A$AP Rocky

Also on Kendall's radar at the time, at least as a cool guy to hang out with, was A$AP Rocky.

Though he was apparently just biding his time before Rihanna was ready to date him, he and Kendall had fun in 2016 and 2017 going to dinner, partying in Miami and New York, making the scene at Coachella and cozying up for Kylie Jenner's epic Met Gala selfie.

Blake Griffin

Then an L.A. Clipper, Blake Griffin was seen squiring Kendall around town more than once starting in August 2017, and she caught a few games courtside.

But once again, it was more of a let's-hang-out-and-have-fun thing than the beginnings of a serious romance. And then Blake was traded to the Detroit Pistons in 2018, so that was that.

Ben Simmons

Ben Simmons actually courted Kendall, the pair meeting in the spring of 2018 and making an effort at meeting up whenever possible despite the point guard being based in Philadelphia. (Ironically, now he's a Clipper, as of 2025.)

Kendall streamed a 76ers game during a photo shoot with Australian Vogue in the spring of 2019, according to the subsequent cover story, and then FaceTimed the Melbourne native to show off her copy of his recent GQ Australia cover.

"For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier," the model told Australian Vogue. "Also I’m very young and right now I feel like relationships aren’t always super-certain."

By the first Monday in May—i.e. the Met Gala—in 2019, they had amicably split up, Kendall foreseeing that her packed schedule could pose too many complications.

As she told Australian Vogue, "Everyone has their own path and their own way of letting the cards fall. Your 20s are for messing up and figuring it out."

Meanwhile, the Internet had sensed a pattern. A fan tweeted a meme in 2019, "Starting 5 of NBA Players Kendall Jenner Dated," that boasted photos of Jordan, Ben, Blake, then-Laker Kyle Kuzma and journeyman D'Angelo Russell.

"This is a playoff team lmao," the fan wrote.

Then it was Kendall with the dunk: She reposted, adding, "2 out of 5 accurate, thanks."

Devin Booker

Kendall dated Devin Booker for almost two years starting in 2020, even bringing the Phoenix Suns shooting guard as her date to sister Kourtney Kardashian's Italian nuptials in May 2022.

But by the following month they were taking time apart, a source telling E! News that, after they got back from their trip, "they started to feel like they weren't aligned and realized they have very different lifestyles."

It was game on again that July, but by November they were going their separate ways, their schedules still not compatible. (Though he bumped D'Angelo out of "Kendall's Starting Five" by the time Kim Kardashian got her hands on a T-shirt version of the meme.)

More recently, a Valentine's Day weekend sighting of the snow-goggles-sporting pair sitting side-by-side at an Aspen restaurant in 2025 showed that one's 20s really are for letting things happen and figuring it out. 

Bad Bunny

Bad Bunny hopped into Kendall's life in 2023, and they were first spotted in February on an apparent double date with Justin and Hailey Bieber.

Then Kendall caught the Puerto Rican artist's set at Coachella in April, and the following month they slipped into a Met Gala afterparty together and twinned at a Lakers game. 

Numerous date nights ensued, and they sat together at the Gucci show during Milan Fashion Week that September, but they were no longer a couple by the end of the year.

However, because if you can stay friends then why not, the duo, who have mutual pals, have reunited numerous times since, all over the world.

And not one to resist a runway-side seat, Bad Bunny was in the audience to see Kendall walk the walk for Calvin Klein Collection's Autumn/Winter 2025 show during New York Fashion Week in February.