Ben Simmons actively pursued a romantic connection with Kendall Jenner, as the two first crossed paths in the spring of 2018. Despite Simmons being based in Philadelphia for his basketball career, they made significant efforts to meet up whenever possible. Fast forward to 2025, and ironically, Simmons is now a member of the Los Angeles Clippers, showcasing the unpredictable nature of both relationships and sports careers.
During a photo shoot for Australian Vogue in the spring of 2019, Kendall made headlines by live-streaming a Philadelphia 76ers game. Following the game, she excitedly FaceTimed Simmons to share her admiration for his recent cover on GQ Australia, reflecting their close connection and support for each other?s careers.
In her interview with Australian Vogue, Kendall expressed how significant and sacred her relationships are to her, stating, “For me, a lot of things are very special and very sacred, like my friends and relationships.” She emphasized her belief that public exposure can complicate things, especially at her young age, where she feels that relationships can lack certainty. This sentiment resonates with many young adults navigating their own complex relationships.
By the first Monday in May?specifically during the glamorous Met Gala of 2019?the couple had decided to amicably part ways. Kendall recognized that her hectic schedule could lead to complications in their relationship, demonstrating her commitment to her career while also valuing her personal connections.
As Kendall remarked in her interview, “Everyone has their own path and their own way of letting the cards fall. Your 20s are for messing up and figuring it out,” highlighting the importance of personal growth and self-discovery during this transformative decade.
Meanwhile, social media began to recognize a pattern in Kendall’s dating history. A fan humorously tweeted a meme in 2019 that featured a lineup titled “Starting 5 of NBA Players Kendall Jenner Dated,” which included notable names like Jordan Clarkson, Ben Simmons, Blake Griffin, Kyle Kuzma, and D’Angelo Russell.
The fan quipped, “This is a playoff team lmao,” showcasing the humorous side of celebrity culture. In response, Kendall playfully added her own touch by reposting the meme with the comment, “2 out of 5 accurate, thanks,” reflecting her sense of humor and engagement with her fanbase.
