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Ben Affleck© Getty

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Ben Affleck's secret crush could be the Hollywood A-list couple we always dreamed of 

It's not the first time he's had interest in one of Brad Pitt's exes


Jovita Trujillo
Senior Writer
APRIL 9, 2025 9:11 PM EDT

Ben Affleck is one of Hollywood’s most eligible bachelors following his split from Jennifer Lopez. Still, according to a new report, he may have his eye on another major A-lister—one with serious acting chops and a history just as high-profile as his own. 

Ben Affleck and Angelina Jolie© The Grosby Group
2001 Vanity Fair Oscar Party

As one of the most iconic names in Hollywood, it's hard to imagine another star on his level. However, according to the Daily Mail, Affleck recently confessed to having a longtime crush on none other than Angelina Jolie.

Jolie, of course, is famously single following her dramatic divorce from Brad Pitt. And it wouldn’t be the first time Ben and Pitt had similar taste—both stars dated Gwyneth Paltrow in the late ‘90s. Pitt was even engaged to her in 1996 before Affleck stepped into the picture.

What makes the Affleck-Jolie idea even more intriguing is that they have more in common than just high-profile exes. They’re both parents—Ben shares three kids with ex-wife Jennifer Garner, while Angelina has six children with Pitt: Maddox, Pax, Zahara, Shiloh, and twins Knox and Vivienne

2001 Vanity Fair Oscar PartyBen Affleck and Angelina Jolie© The Grosby Group
2001 Vanity Fair Oscar Party

They’re also both respected in the industry, not just as actors but as directors. Affleck is behind The Town and Argo, while Jolie has helmed projects like Unbroken and First They Killed My Father.

According to the Daily Mail source, Affleck has long admired Jolie. “Ben said that he always thought that she was very hot and has admired how she has navigated her career. He has called her smart,” the source claimed. “He also thinks it’s pretty cool that she has directed films too—something he has done many times. They would certainly have a lot to talk about over dinner.”

He also noted they’re close in age—Affleck is 52 and Jolie is 49—which he sees as a plus.

Of course, just because Affleck has a crush doesn’t mean the feeling is mutual. Jolie has said she’s currently focused on being a mother to her six kids. But according to the source, that hasn’t deterred Affleck’s interest.

Earlier this year, Affleck and Garner were photographed playing paintball with their kids, sparking rumors of a romantic reunion© x17/The Grosby Group
Earlier this year, Affleck and Garner were photographed playing paintball with their kids, sparking rumors of a romantic reunion

The rumor comes on the heels of renewed speculation about the Air director's relationship with his ex-wife Jennifer Garner

The two were recently spotted together at their son Samuel’s birthday party, where Affleck was seen giving her a waist grab and a side hug that had some fans raising their eyebrows. Reports later claimed Garner’s boyfriend, John Miller, wasn’t thrilled about the moment and may have asked for firmer boundaries. Since then, there’s been noticeably less chatter about Affleck and Garner’s co-parenting outings.

As for Affleck and Jolie, they’ve crossed paths many times over the years. In 2001, they were photographed at the Vanity Fair Oscar party, with Ben whispering in the Salt star's ear as she smiled in a sleek white suit. And in 2014, they were snapped locking eyes at the Hollywood Film Awards.

Angelina Jolie and Ben Affleck at the 18th Annual Hollywood Film Awards at The Palladium on November 14, 2014© Getty
Angelina Jolie and Ben Affleck at the 18th Annual Hollywood Film Awards at The Palladium on November 14, 2014

Could a full-blown Hollywood romance be next? Time will tell.

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