The Weeknd previously dated Bella Hadid in 2015, breaking up in 2016 and reuniting in 2017 after he had a 10-month fling with Selena Gomez. They split for good in 2019. Meanwhile, Jolie separated from Brad Pitt in 2016, and they share six kids: Maddox, 20, Pax, 17, Zahara, 16, Shiloh, 15, and twins Vivienne and Knox, 13. Prior to her meetups with The Weeknd, it was reported that the “Lara Croft: Tomb Raider” star was reconnecting with ex-husband Jonny Lee Miller. She was photographed leaving her British ex’s apartment building in Dumbo in June.