Harry Styles

"No story, we're friends," Kendall Jenner told E!'s Giuiliana Rancic successful November 2013 of her and Harry Styles' narration presumption aft they were spotted astatine meal successful West Hollywood. "He's cool."

But subsequent sightings successful New York and London adjacent had Brody Jenner guessing that, immoderate was up betwixt them, his half-sister was successful the driver's seat.

"I'm definite she's having a amusive clip with him," helium told the New York Daily News that December. "She has a precise level head, large caput connected her shoulders. But they are some truthful young."

Then 18 and 20, Kendall and Harry ne'er mislaid each other's numbers, reuniting for stop-the-presses outings successful 2016 (including a PDA-packed enactment aboard a yacht), 2018, 2020...

So, astatine the precise least, a lasting relationship was successful the cards for the duo, who sparked romance rumors again arsenic precocious arsenic 2022, pursuing Harry's divided from Olivia Wilde.

"She and Harry are conscionable bully friends," a root told E! News astatine the time. "They remained affable implicit the years and person kept successful touch."

Justin Bieber

Kendall ne'er dated Justin Bieber, but they were around each different enough that immoderate radical speculated they were.

Enough truthful that it was brought up during a Nightline interrogation Kendall gave successful 2014.

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

Moreover, Kendall has been besties with Hailey Bieber for ages, and she's been known to treble day with the joined couple erstwhile she has a plus-one successful her life, oregon conscionable chill with the duo connected her own.

Nick Jonas

In August 2015, freshly azygous Nick Jonas was rumored to beryllium seeing Kendall aft being introduced into her orbit by member Joe Jonas and his then-girlfriend Gigi Hadid.

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

"Kendall is great," helium told E! News astatine the time, "and people with her being bully friends with Gigi and with Joe and Gigi dating, determination are times we'll beryllium successful the aforesaid spot and we each bent out."

Jordan Clarkson

There were rumored fireworks betwixt Jordan Clarkson, past playing for the Los Angeles Lakers, and Kendall implicit Fourth of July successful 2016—and they seemed to inactive beryllium getting on swimmingly successful November, erstwhile hoops play was underway. 

Jordan was besides a impermanent astatine Kendall's star-studded 21st day party that month, but their transportation remained successful the casual zone.

A$AP Rocky

Also on Kendall's radar astatine the time, astatine slightest arsenic a chill feline to bent retired with, was A$AP Rocky.

Though helium was seemingly just biding his clip earlier Rihanna was acceptable to day him, helium and Kendall had amusive successful 2016 and 2017 going to dinner, partying successful Miami and New York, making the country 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 astir town much than erstwhile starting successful August 2017, and she caught a fewer games courtside.

But erstwhile again, it was much of a let's-hang-out-and-have-fun happening than the beginnings of a superior romance. And past Blake was traded to the Detroit Pistons successful 2018, so that was that.

Ben Simmons

Ben Simmons really courted Kendall, the brace gathering successful the outpouring of 2018 and making an effort astatine gathering up whenever imaginable contempt the constituent defender being based successful Philadelphia. (Ironically, now he's a Clipper, arsenic of 2025.)

Kendall streamed a 76ers crippled during a photograph sprout with Australian Vogue in the outpouring of 2019, according to the consequent screen story, and past FaceTimed the Melbourne autochthonal to amusement disconnected her transcript of his recent GQ Australia cover.

"For me, a batch of things are precise peculiar and precise sacred, similar my friends and relationships, and I personally deliberation that bringing things into the nationalist makes everything truthful overmuch messier," the exemplary told Australian Vogue. "Also I’m precise young and close present I consciousness similar relationships aren’t ever super-certain."

By the archetypal Monday successful May—i.e. the Met Gala—in 2019, they had amicably divided up, Kendall foreseeing that her packed docket could airs excessively galore complications.

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

Meanwhile, the Internet had sensed a pattern. A instrumentality tweeted a meme successful 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 simply a playoff squad lmao," the instrumentality wrote.

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

Devin Booker

Kendall dated Devin Booker for astir 2 years starting successful 2020, adjacent bringing the Phoenix Suns shooting defender as her date to sister Kourtney Kardashian's Italian nuptials successful May 2022.

But by the pursuing period they were taking clip apart, a root telling E! News that, aft they got backmost from their trip, "they started to consciousness similar they weren't aligned and realized they person precise antithetic lifestyles."

It was crippled connected again that July, but by November they were going their abstracted ways, their schedules inactive not compatible. (Though helium bumped D'Angelo retired of "Kendall's Starting Five" by the clip Kim Kardashian got her hands connected a T-shirt mentation of the meme.)

More recently, a Valentine's Day play sighting of the snow-goggles-sporting brace sitting side-by-side astatine an Aspen edifice successful 2025 showed that one's 20s truly are for letting things hap and figuring it out. 

Bad Bunny

Bad Bunny hopped into Kendall's life successful 2023, and they were archetypal spotted successful February connected an evident treble day with Justin and Hailey Bieber.

Then Kendall caught the Puerto Rican artist's set astatine Coachella successful April, and the pursuing period they slipped into a Met Gala afterparty together and twinned astatine a Lakers game. 

Numerous day nights ensued, and they sat together astatine the Gucci amusement during Milan Fashion Week that September, but they were nary longer a mates by the extremity of the year.

However, due to the fact that if you tin enactment friends past wherefore not, the duo, who person communal pals, person reunited galore times since, all implicit the world.

And not 1 to defy a runway-side seat, Bad Bunny was successful the assemblage to spot Kendall locomotion the walk for Calvin Klein Collection's Autumn/Winter 2025 amusement during New York Fashion Week successful February.