This is a question we never thought we’d ask: Are Angelina Jolie and The Weeknd dating? Here’s what we know. Jolie, 46, and The Weeknd, 30, were photographed together on Saturday, September 25, at a dinner that lasted 2.5 hours.
According to The Daily Mail, Jolie and The Weeknd were seen at Giorgio Baldi in Santa Monica, where were seated in a private section for 2.5 hours. For the dinner, both Jolie and The Weeknd wore black. The Weekend dressed in a collared black top and pants, while Jolie wore a black trench coat with heels and a Saint Laurent bag. The Daily Mail also reported that Jolie and The Weeknd took his black SUV to his Bel air home after dinner.
The outing comes two months after Page Six reported that Jolie and The Weeknd went to dinner together at the same restaurant on June 30, where they also dined for several hours. The two were photographed leaving the restaurant separately as to not be seen together. For the dinner, Jolie wore a black silk dress and a tan trench coat, while The Weeknd dressed more casual in an all-denim look with black boots. (See the photos here.)
A source told Page six that Jolie and The Weeknd weren’t “trying to hide” their rumored date, which could be related to The Weeknd’s plan to transition to acting. “They’re clearly not trying to hide [the dinner date],” the insider said. “He’s definitely focused on getting to the movie business. He has the new HBO series he’s starring in.”
The dinner comes two weeks after Jolie reunited with her ex-husband Jonny Lee Miller in June. At the time, Jolie—who was married to the British actor from 1996 to 1999—was photographed arriving at Miller’s apartment in Dumbo, Brooklyn, with an expensive bottle of Peter Michael wine. Jolie was in New York City at the time with her six kids—Shiloh, 15, Vivienne, 12, Maddox, 19, Zahara, 16, Pax, 17, and Knox, 12—to celebrate her belated 46th birthday.
A source told The Sun at the time that Jolie described Miller to her kids, whom she shares with her ex-husband Brad Pitt, as her “first love” and that she even introduced Miller to one of her youngest children, Knox. “On her first evening with Jonny, Angelina only took Knox along, and they got on like a house on fire,” the insider said. “Knox is a sweet kid, and I imagine she decided he was the easiest one to begin introductions with.”
The insider continued, “[Jonny is a] guy she’s always spoken so fondly about. They only hung out for a short while at Jonny’s apartment, but they seemed to get along well.”
Days after she was first seen arriving at Miller’s apartment, Jolie was photographed at his home again with her second eldest son, Pax. According to The Sun’s source, Pax, who is 17, is considering moving to New York City for college, which is why Jolie wanted him to meet Miller.
“Angie is very happy because Pax keeps making noise about moving to New York someday soon, maybe even for school,” the insider said. “She’s glad he’ll have someone she trusts around for him to go to for advice or just to see a friendly face.”