Who Did Kendall Jenner Spend New Year's Eve With?

Are Kendall Jenner and ex Ben Simmons getting back together? Nothing is super clear yet, but in a video obtained by TMZ, the two rang in the new year together! The former couple were in Downtown Philadelphia heading into a rooftop restaurant named Attico as they were seen walking in at the same time around 11:30 p.m. local time as the super model wore a mini shirt dress, while the NBA player sported an all-black ensemble. And after a few photos surfaced online, fans are convinced they may have shared a New Year's Eve kiss when the clock struck midnight.

According to one source who spoke with E! News, it seems like the two may be giving their relationship a second try.

"They took a break because it was difficult to sustain a relationship with their schedules. But they have stayed in touch and there was never a messy breakup or hard feelings," the insider said. "Kendall has spent a lot of time with Ben over the last few weeks in Philadelphia. She's been flying to see him whenever she can."

The source added, "They really like each other and want to be a part of each others lives. They are so comfortable with each other and always laughing. They work well together."

Jenner confirmed the pair's relationship the first time around back in Feb. 2019 when making a guest appearance on The Ellen DeGeneres Show. DeGeneres asked her about being courtside at a 76ers game but Jenner played coy most of the conversation. When DeGeneres pushed a little more, saying that the Keeping Up With the Kardashians star was obviously dating him, prodding further into how long, to which Jenner responded with "for a bit now."


Jenner has managed to stay pretty private over the years with her relationships. While her sisters have been very open out theirs, Jenner says she prefers to keep things under wraps in case it doesn't work out. It was hard for her to keep private about she and Simmons though because the two were photographed almost everywhere they went together, including the times Jenner appeared at his games — which she continues to do.

Just three months later, sources confirmed the pair had split in May claiming that the two were on a break. Again, Jenner didn't really say much about what happened or if she anticipated them ever getting back together, so fans were left in the dark on that matter. However, now that the two are seen hanging out again, onlookers are thrilled!