The "Maleficent" actress, 46, and the "After Hours" singer, 31, were snapped leaving Giorgio Baldi restaurant in matching all-black outfits and masks.
They were also spotted at the same swanky Italian eatery in late June. According to The Daily Mail, Jolie and The Weeknd (born Abel Tesfaye) dined for over two hours and then got into the same SVU together.
A source close to The Weeknd previously told Page Six that their relationship might be business-focused. "They’re clearly not trying to hide [the dinner date]," the source said. "He’s definitely focused on getting to the movie business. He has the new HBO series he’s starring in."
The former Super Bowl halftime show performer was last linked to model Bella Hadid. They began dating in 2015, broke up in 2016, and then reunited in 2017 only to split again in 2019.
During their break, the "Blinding Lights" crooner had a 10-month relationship with Selena Gomez.
Meanwhile, Jolie is locked in a bitter court battle over custody of her children with ex-husband Brad Pitt. The former couple shares six kids: Maddox, 20, Pax, 17, Zahara, 16, Shiloh, 15, and 13-year-old twins Vivienne and Knox.
Maddox is not included in the court battle due to his age.
Jolie opened up about her marriage to Pitt in an interview published Saturday by The Guardian. She admitted she feared for the safety of her entire family while she was married to Pitt.
"Yes, for my family," she told the outlet. "My whole family."
However, the "Eternals" star claimed she wants the family to move forward, despite feeling "broken" by her experiences.
"I want us to heal and be peaceful. We'll always be a family," Jolie said.
Fox News' Lauryn Overhultz contributed to this report.