Ben Affleck Has Secret Crush on Angelina Jolie

Published 1 weeks ago on Apr 09, 2025

Ben Affleck Secretly Crushing on Angelina Jolie — Years After Both Dated Gwyneth Paltrow.

Ben Affleck may be single again, but it seems he already has his sights set on a familiar face in Hollywood — none other than Angelina Jolie.

According to a new report by Daily Mail, the Argo director recently revealed to a friend that his ultimate movie star crush is Jolie, a fellow Oscar-winning actress and the former wife of Brad Pitt. The revelation comes as both Affleck, 52, and Jolie, 49, are single — and have more in common than just their A-list status.

Ben Affleck’s Surprising Pick: Angelina Jolie

While it may come as a surprise to some, insiders claim that Affleck has long admired Jolie, not just for her beauty but for her intelligence and multifaceted career. The Gone Girl actor is said to be impressed with how Jolie has managed to navigate fame, philanthropy, motherhood, and directing with remarkable poise.

“Ben said that he always thought she was very hot and has admired how she has navigated her career,” a source told Daily Mail. “He’s called her smart and said it’s cool that she directs films too — something he’s done himself with The Town and Argo.”

The source added that Affleck and Jolie, who have occasionally crossed paths at Hollywood events over the years, “would certainly have a lot to talk about over dinner.”

Angelina Jolie: Single Since Her Split from Brad Pitt

Angelina Jolie, who finalized her divorce from Brad Pitt in 2016, has not been publicly linked to anyone romantically since the split. The Oscar winner has instead focused on raising her six children — Maddox, Pax, Zahara, Shiloh, and twins Knox and Vivienne — while continuing her humanitarian efforts and film work behind the camera.

In previous interviews, Jolie has emphasized that her priority remains her children, and that dating hasn’t been on her radar. Still, Affleck reportedly isn’t deterred.

“Ben likes that they are close in age,” the insider noted. “She’s 49, and he’s 52. That makes things more relatable.”

A History of Shared Hollywood Romances

This wouldn’t be the first time Affleck and Pitt crossed romantic paths. In the late '90s, both men dated Gwyneth Paltrow. Pitt, now 60, was engaged to the Shakespeare in Love actress from 1994 until 1997, while Affleck dated her from 1997 to 2000.

Currently, Pitt is in a serious relationship with 32-year-old jewelry executive Ines de Ramon. The couple have reportedly grown close over the past year, with Pitt said to be “smitten” with his younger partner.

Meanwhile, Affleck’s most recent relationship — and marriage — with Jennifer Lopez officially ended earlier this year, marking the second time their famously passionate romance came to a close.

A Spark Between Ben and Angelina?

Though Ben Affleck and Angelina Jolie have never been romantically linked, there have been public moments over the years where sparks were visible.

At the 2001 Vanity Fair Oscar party, Affleck was spotted whispering into Jolie’s ear as she beamed in a striking white suit — worn without a shirt. Their chemistry seemed undeniable. Then, in 2014, the pair were photographed gazing into each other’s eyes during the Hollywood Film Awards, sparking rumors of a deep mutual admiration.

Insiders suggest these moments were more than fleeting. “They light up when they see each other,” one source noted.

Affleck Reflects on Jennifer Lopez Divorce

The news of Affleck’s reported crush on Jolie comes amid candid reflections on his recent divorce from Jennifer Lopez. Speaking to GQ for the April issue, Affleck shared that the end of their relationship wasn’t due to scandal or dramatic fallout, but rather an ordinary evolution of life.

“There’s no scandal, no soap opera, no intrigue,” he explained. “The truth is, when you talk to somebody — ‘Hey, what happened?’ — well, there is no, ‘This is what happened.’”

Affleck emphasized that despite their differences, he still has deep respect for Lopez, 55, calling her an icon and noting that she handled fame more gracefully than he ever could.

“My temperament is to be a little bit more reserved and private than hers,” he admitted, adding that he participated in Lopez’s 2024 Amazon documentary The Greatest Love Story Never Told out of love and support for her.

“I believe in her. I want people to see that,” he said. However, he was quick to clarify that the documentary wasn’t a catalyst for their split. “It’s not like you can watch that documentary and go, ‘Oh, now I understand the issues that these two had.’”

J.Lo Moves Forward with Work and Family

Jennifer Lopez, for her part, seems to be moving on with confidence. The Marry Me star is currently filming her new romantic comedy Office Romance in New York City alongside Ted Lasso’s Brett Goldstein.

This week, she took to Instagram to share a glamorous photo in a silver outfit, listing what she’s grateful for — a subtle message that she’s finding strength in gratitude and moving forward.

Last weekend, Lopez spent quality time with her 17-year-old daughter Emme, attending the Broadway premiere of Othello starring Denzel Washington and Jake Gyllenhaal. The mother-daughter duo donned stylish dark ensembles for their night out, with J.Lo in a bedazzled navy two-piece by Zuhair Murad and Emme in a sharp black pinstriped suit.

Jennifer later posted: “Othello premiere with the best date ever ⭐️,” a touching tribute to her child.

She also recently celebrated her twins’ 17th birthday on Instagram with a heartfelt video montage. “Seventeen. I love you beyond forever 🥥🥥,” she captioned the post, filled with candid family memories.

Lopez shares twins Emme and Max with her ex-husband Marc Anthony, 55, and has frequently expressed how motherhood is her greatest role. “It’s unconditional love,” she told People. “I just feel like they’re super special. I can’t wait to see what they do.”

Will Hollywood’s Next Power Couple Be Ben and Angelina?

As Ben Affleck steps into a new chapter following his split from Lopez, speculation is swirling about whether his admiration for Angelina Jolie could blossom into something more.

With both stars single, mature, and fiercely devoted to their children and careers, fans can’t help but wonder if the long-simmering chemistry between the two might finally ignite into a full-blown Hollywood romance.

Only time will tell if these two Oscar winners — each with a complicated romantic past — will find common ground over dinner, directing, and perhaps, love.

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