Inside Kendall Jenner’s Quietly Stacked Dating History

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.”