Ben Simmons indeed pursued Kendall, with the couple first meeting in the spring of 2018 and making efforts to connect whenever possible, despite the point guard residing in Philadelphia.
Kendall watched a 76ers game during a photo shoot with Australian Vogue in the spring of 2019, as noted in the subsequent cover story, and later FaceTimed the Melbourne native to showcase her copy of his recent GQ Australia cover.
“For me, many things are very special and very sacred, like my friends and relationships, and I personally believe that bringing things into the public makes everything so much messier,” the model shared with Australian Vogue. “Also I’m very young and currently I feel like relationships aren’t always super-certain.”
By the first Monday in May—specifically, the Met Gala—in 2019, they had amicably parted ways, with Kendall anticipating that her busy schedule could create too many complications.
As she expressed to 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 noticed a trend. A fan tweeted a meme in 2019, “Starting 5 of NBA Players Kendall Jenner Dated,” featuring photos of Jordan, Ben, Blake, then-Laker Kyle Kuzma, and journeyman D'Angelo Russell.
“This is a playoff team lmao,” the fan commented.
Kendall then made a slam dunk: She reposted it, adding, “2 out of 5 accurate, thanks.”

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