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According to TMZ, Kendall and Philadelphia 76ers star Ben Simmons spent New Year’s Eve in downtown Philadelphia, where Simmons rented out rooftop restaurant Attico. Simmons and Jenner reportedly showed up at about 11:30 p.m. and stayed for the clock to hit midnight.
This on-again-off-again couple is hard to keep track of. They were first spotted together in June 2018, but by September, Jenner was seen making out with Anwar Hadid in New York City during New York Fashion Week. In January 2019, Jenner sat next to Simmons’s mom, Julie, at a 76ers game while they watched him play.
“They’re on a break,” a source said. “The relationship ran its course. She’s spending time with her friends and back to being in fun mode.”Jenner was at one of Simmons’s games again.
By December 2019, Jenner was back at one of Simmons’s games.
There has been no confirmation from either party that things are heating up again, but it’s pretty obvious that Jenner is spending a lot of her time with one particular person right now.