Kendall Jenner, 24, and Ben Simmons, 23, seem very much back on! The former couple rang in the new decade together, celebrating New Year’s Eve in Philadelphia based on photo and video obtained by TMZ. Kendall and Ben were spotted strolling into swanky rooftop restaurant Attico around 11:30 p.m., where the 76ers were hosting a soiree in trendy downtown. The supermodel stunned for an evening out, rocking a black button-down minidress, and a distinct pair of Amina Muaddi heels — a go-to for Kendall lately and her BFF Gigi Hadid — with the designers’ signature flare heel. Ben himself looked ready for the festivities in a silver sequin adorned bomber jacket and an all-black ensemble.
Rumors began swirling that Kendall and Ben might be back together on after the brunette was seen in Philly at a 76ers game on Dec. 13! Though she attempted to stay out of the spotlight in a high-up box seat and a simple black ensemble, eagle eyed fans quickly noted she was both at the game and sitting with Ben’s friends. “Kendall with Ben’s friends arriving Sixers game in Philly, today (12/13) BENDALL IS BACK !!!” a fan posted to Twitter, including a video of Kendall at the arena. Ben and Kendall started hanging out in May 2018, and sparked romance rumors after a low key date at The Nice Guy and a night together at the luxe Waldorf Astoria hotel in Beverly Hills. At the time, it was reported that they had been dating a few weeks.
Shortly after, a love triangle seemingly emerged as Kendall was spotted making out with Gigi and Bella Hadid‘s younger brother Anwar Hadid, 20, at a CFDA Awards after party in NYC! The sexy hook up came only a day after she was seen bike riding with Ben. Later that fall, the Stuart Weitzman model was seen hanging court side at Ben’s games in Philly and wasn’t shy about being photographed or spending time with Ben’s mom. Of the Kardashian-Jenner clan, Kendall has been the most private about her love life, with the exception of her several sightings with Ben. She even appeared to be watching his game and FaceTiming her boo during a break from an interview with Vogue Australia in May 2019.
Sadly, the pair called things quits later that month. “The relationship ran its course,” People reported at the time. “She’s spending times with her friends and back to being in fun mode.” The news also happened to coincide with Ben’s team making the NBA playoffs and a busy time for Kendall’s modeling campaigns, making it difficult to see each other.