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Ben Simmons and Kendall Jenner first crossed paths in the spring of 2018, embarking on a relationship that persisted despite the geographical challenge posed by Simmons’ Philadelphia base. Interestingly, as of 2025, Simmons has transitioned to playing for the Clippers.
During a photo shoot with Australian Vogue in the spring of 2019, Kendall managed to catch a 76ers game, as detailed in the magazine’s cover story. She even FaceTimed the Melbourne-born Simmons to flaunt her copy of his recent GQ Australia cover.
In a conversation with Australian Vogue, the model shared, “There are many things I hold dear and consider sacred, like my friendships and relationships. I believe exposing them to the public eye only complicates matters. Plus, I’m still quite young, and I think relationships at this age can be unpredictable.”
By the time the Met Gala rolled around in May 2019, the couple had decided to part ways on good terms. Kendall anticipated that her busy lifestyle might lead to too many hurdles.
Reflecting on her approach to life, she remarked to Australian Vogue, “Everyone forges their own path and handles life’s challenges uniquely. Your 20s are a time for making mistakes and discovering yourself.”
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.”