The pair were seen hanging out on Saturday, January 18, at Moxy East Village late into the evening, The New York Post’s Page Six reported on Monday, January 20.
The outlet reports that the pair arrived together at the Little Sister Lounge after Simmons’ Philadelphia 76ers beat the New York Knicks at Madison Square Garden. The model and the athlete hung out with Canadian rapper Nav before leaving together at 2 a.m.
Simmons, 23, and Jenner, 24, was also spotted grabbing a bite to eat at Bubby’s in Tribeca on Sunday, January 19.
The Keeping Up With the Kardashians star sparked reconciliation rumors after she rang in the new year with her former flame at a party in Philadelphia on New Year’s Eve.
The basketball star reportedly rented out Attico’s rooftop restaurant for an end of 2019 bash. The pair walked into the celebration together at about 11:30 p.m., TMZ reported at the time.
A few weeks prior, the model attended one of her exes’ games in Philadelphia as the team played the New Orleans Pelicans on December 13. The reality star was photographed watching the game from a box seat at the Wells Fargo Center.
Us Weekly reported in May 2018 that the duo was casually dating. They called it quits after four months of dating in September 2018. Two months later, the former lovebirds rekindled their romance but parted ways once again in May 2019.
A source told Us at the time that the duo’s “sudden” separation came as a result of “things [winding] down” between them.
“They were getting serious for a bit, but were starting to cool off recently,” another insider told Us in May. “They’re so busy doing their own things and realize they’re young and want to have fun.”
Throughout their relationship, Jenner opted to keep it as quiet as possible, after seeing how her sisters’ love lives were scrutinized in the past.
“I got a glimpse of how my sisters dealt with [the attention] and it’s cool to learn from that,” the model told Vogue Australia in its June 2019 issue. “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.”
She continued, “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 [what it’s going to be]. 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.”