TMZ reports that the supermodel, 24, and the NBA star, 23, attended a New Year’s Eve party at Attico in downtown Philadelphia, where the 76ers player rented out the rooftop restaurant. The pair walked into the celebration together at about 11:30 p.m. and were there as partygoers counted down to midnight.
Just weeks earlier, the Keeping Up With the Kardashians star was spotted at the Wells Fargo Center in Philadelphia when Simmons and his team took on the New Orleans Pelicans on December 13.
Us Weekly first reported that Jenner and the Australian athlete were casually dating in May 2018. They split four months later but reconciled in November 2018 before calling it quits for a second time this past May.
“They were getting serious for a bit, but were starting to cool off recently,” an insider told Us at the time. “They’re so busy doing their own things and realize they’re young and want to have fun.”
Shortly before their breakup, Jenner spoke to Vogue Australia about why she kept her relationship with Simmons private.
“I got a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that,” she said. “For me, a lot of things are very special and very sacred, like my friends and relationships, and I personally think that bringing things into the public makes everything so much messier.”
“I’m very young and right now 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 [it’s going to be],” she continued. “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. Like once everyone is let in, you’re letting all these opinions into your relationships, and I don’t think that’s fair.”
When Vogue asked if an engagement could be on the cards, Jenner responded, “Maybe,” adding, “Definitely not now, but maybe one day.”
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