News Kendall Jenner Spent New Year's Eve with Ben Simmons The two reportedly went "on a break" back in May. By Kimberly Truong Kimberly Truong Kim Truong is a writer focusing on news, entertainment, and culture. She is a graduate of Fordham University. Her work has appeared on The Cut, Self, Refinery29, and BBC America. InStyle's editorial guidelines Updated on January 2, 2020 @ 09:45AM Pin Share Tweet Email After reportedly going on a "break" earlier this year, it looks like Kendall Jenner and Ben Simmons are spending more time together again. In a video obtained by TMZ, the two were seen on New Year's Eve together in Philadelphia, where he rented out rooftop restaurant Attico for the festivities. According to the outlet, they arrived at around 11:30pm to ring in the new year together. Last summer, it was reported that Jenner and Simmons were "on a break," as a source told People, "The relationship ran its course. She’s spending time with her friends and back to being in fun mode." "Fun mode" is apparently over, because she was seen cheering him on last month at one of his basketball games, and this latest sighting seems to confirm that they're at least friends. James Devaney/Getty Images Jenner and Simmons have been linked since mid-2018, and before their reported break, she had spoken in an interview about "maybe one day" getting married, but added, "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]." Kendall Jenner's Hair Changed — Again Well, a whole new decade seems like the perfect time to reconcile a romance.