Kendall Jenner Spends New Year's Eve With Ex Ben Simmons

Kendall Jenner Cozies Up to Rumored Boyfriend Ben Simmons at Khloe Kardashian's Party
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The 24-year-old model was spotted with the 23-year-old NBA pro in downtown Philadelphia.

History may already be repeating itself in 2020.

On New Year's Eve, Kendall Jenner was spotted out with her ex-boyfriend, Ben Simmons, in Philadelphia, Pennsylvania. According to TMZ, which posted a pic of the 24-year-old model and 23-year-old NBA pro, the two were seen downtown where Simmons had rented out the rooftop of Attico for a NYE party. The website reports that Kendall and Ben arrived to the venue at 11:30 p.m. and stayed for the countdown to 2020.

Last May, a source told ET that the pair were no longer dating after initially having sparked romance rumors a year prior. 

"Kendall and Ben are not together, but the two are on good terms," the source said at the time. "Both Kendall and Ben are extremely busy, and for now the relationship doesn't work for them. Kendall and Ben have taken breaks in the past and have gotten back together."

"They are really good at knowing when the relationship works for them and when it doesn't," the source added. "Kendall is looking forward to a busy summer of working, but also spending time with her friends."

A few months prior to their breakup, Kendall, who is notoriously private, confirmed that she'd been dating Ben "for a bit now" during an appearance on The Ellen DeGeneres Show.

In a later interview with Vogue Australia, she explained why she rarely opens up about her dating life.

"A relationship is only meant to be between two people, and the second you make it the world's business is when it starts messing with the two people mentally," she said. "Like, once everyone is let in, you're letting all these opinions into your relationships, and I don't think that's fair."

"I'm very young and right now," Kendall added. "I feel like relationships aren’t always super-certain, and I don’t want to bring too much attention to something if you don't really know long term [what it's going to be]."