The 46-year-old actress made jaws drop when she was spotted at dinner with the 31-year-old singer on Wednesday night.
According to Page Six, they were "clearly not trying to hide [the dinner date]" -- clearly evident by the place they chose to eat.
Instead of going to a super-secret staple, Angelina met The Weeknd at one of the hottest celebrity spots in Los Angeles.
The duo went to Giorgio Baldi in Santa Monica. The high-end Italian eatery is known for drawing A-listers, and with that, paparazzi.
Despite spending hours in the restaurant together, there were no shots of the unlikely pair leaving together.
Instead, Angelina carefully slipped out of the dinner establishment solo but she didn't go unnoticed.
Pitt's ex-wife took her fashion inspiration from Inspector Gadget, wearing a tan buttoned trench coat over her black silk dress.
The After Hours singer -- whose real name is Abel Tesfaye -- exited by himself moments later.
He kept it casual, paying homage to his Canadian roots in a denim jacket and jeans.
While Angelina wore a mask over her face for safety, The Weeknd chose to expose his facial hair sans any protection.
Despite choosing possibly the most romantic place on the west side, sources claim their late-night rendezvous could be all about business.
Angelina and The Weeknd have a lot in common, despite their 15-year age gap.
When it comes to love, both have had relationships in the public eye.
The Weeknd has famously dated model Bella Hadid on and off again for several years. Between one of their breakups, the singer managed to slide into a relationship with Selena Gomez.
As for Angelina, she's been married a total of three times.
Her first husband is Jonny Lee Miller, whom she still sees on occasion. After Jonny, she said "I do" to actor Billy Bob Thornton.
In 2014, Angelina officially tied the knot with Pitt, but their marriage ended in divorce years later.
The duo is still battling it out in court over their six children despite a judge giving Pitt joint custody.