While Simmons’ play took center stage, the 22-year-old made plenty of headlines off the court as well, specifically when it came to his dating life. He spent the bulk of his offseason in Los Angeles, partially due to his relationship with model Kendall Jenner. Although the two attempted to keep things somewhat lowkey, it didn’t take long for the media to jump all over the relationship.
But their relationship didn’t start without drama following closely behind, and that partially came thanks to Simmons’ ex-girlfriend Tinashe. The Sixers star and singer dated for six months before coming out publicly, as College Candy revealed, but Simmons ended it in 2018, which is where the fun begins.
Tinashe Around Ben Simmons and Kendall Jenner
The rumblings pointed to Simmons and Jenner starting to date right around the time he called it off with Tinashe, but we’ll never know the exact timeline. One thing we do know is that the 23-year-old model had no interest in the drama his ex-girlfriend brought to the table.
As Melody Chiu and Natalie Stone of People revealed, Jenner was interested in keeping her relationship private and called it “annoying” when addressing the Tinashe situation.
“She’s being very private about her relationship with Ben. Kendall’s really different from her sisters in that sense,” a source close to Jenner, 22, tells PEOPLE.
“She honestly doesn’t want people talking about who she’s dating and is very protective of her personal life,” the source explains about the Keeping Up with the Kardashians star. “She hates the attention and it’s been annoying that the drama with Tinashe has come up.”
Things got so bad that the singer wound up in the same club/bar as Simmons and Jenner, leading to a pretty uncomfortable situation. While the Tinashe topic was seemingly a hot-button one, it wasn’t what led to the breakup.
Simmons and Jenner Were off … Then Back On?
When the news came that Simmons and Jenner had apparently broken up around September, it was rumored both sides moved on quickly. For the 76ers guard, Sports Gossip cited back-and-forth on social media with the ex of Phoenix Suns guard Devin Booker, model Ashley Moore. The site first revealed Moore dropping some eye emojis on one of Simmons’ Instagram photos and the Sixers guard giving some attention back.
There didn’t seem to be confirmation of Simmons with Moore or any indication they were official, but the same couldn’t be said for Jenner. As Carlos Greer of Page Six cited, she was caught getting close with Gigi and Bella Hadid’s brother, Anwar, at a party after the breakup.
“Kendall was sitting with Anwar all night and made out with him for quite some time,” a spy said. “They didn’t give a damn who saw them.”
And now, here we are.
After both Simmons and Jenner had reportedly moved on, the script flipped back in the other direction in early November. Ian Mohr of Page Six revealed the two were together at the Elbow Lane bowling alley in Philadelphia early in the 2018-19 NBA season.
Said a source, “Kendall and friends were celebrating the 76ers’ win against the LA Clippers. Kendall arrived in Philadelphia on a private jet after spending Halloween with her sisters.”
The source further told us, “The party was drinking wine and having some bites as they bowled . . . Kendall and Ben were having a great time with friends partying after his hometown victory.”
Rumblings had been picking up that the Sixers star wanted to get back with Jenner, but nothing was heard until this. Based on how private Jenner apparently tried to keep things the first time, there’s a good chance we may not know the truth behind this for a while.
As Drew Corrigan of House of Highlights revealed, Jenner was in attendance for Simmons’ game with the 76ers on Friday, November 23.
Roughly two weeks or so after that, Daily Mail revealed that Simmons and Jenner went ice skating in Philly. It seems the model is spending a fair amount of time in the basketball star’s hometown.
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by – heavy.com