Breakups can be messy, but some take drama to another level—especially when Hollywood is involved.
For Ben Affleck and Ana de Armas, their split came with an unexpected twist: a life-sized cardboard cutout of Ana being tossed in the trash outside Affleck’s home, captured in viral paparazzi photos.
While it wasn’t the actress herself being discarded, the message was clear—the relationship was over.
A Quarantine Love Story
Affleck and de Armas first met in 2019 on the set of Deep Water, where they played an on-screen couple.
By early 2020, their romance had spilled into real life, and they were soon vacationing together.
As the COVID-19 pandemic shut the world down, they chose to quarantine together at Affleck’s lavish $19 million Pacific Palisades home.
During those months, they were inseparable—ordering takeout, going on neighborhood walks with their dogs, and embracing a cozy domestic routine.
According to sources, their time in lockdown intensified their bond, making it feel like a whirlwind love story straight out of a movie.
From Passion to Public Trash
Despite their strong connection, the romance eventually crumbled.
By early 2021, the quarantine bubble had burst, and so had their relationship.
Affleck’s dramatic disposal of Ana’s cardboard cutout signified the end of their chapter, with the public spectacle leaving little room for doubt.
Not long after, Affleck rekindled his romance with Jennifer Lopez, a love story that had first captivated the world in the early 2000s.
Within months of his split from Ana, Affleck was fully back with JLo, and by July 2022, they were married in a Las Vegas ceremony.
However, their second chance at love didn’t last either—JLo filed for divorce in August of last year.
Regret and Reflection
Now, sources claim Affleck may be rethinking the choices he made.
Allegedly, his relationship with Ana ended because she wanted marriage while he wasn’t ready to commit.
Looking back, he wonders if he made the wrong decision.
“He ended up marrying Jennifer after not being able to commit to Ana,” an insider shared.
“In hindsight, he realizes how wrong that was and feels he could have avoided the JLo drama by staying with Ana.”
Adding to the intrigue, Ana has recently been linked to Top Gun star Tom Cruise after the two were spotted dining together on Valentine’s Day.
Though sources insist their connection is strictly professional, the rumors are enough to make people wonder—especially Affleck.
A Love That Could Have Been?
During their time together, Affleck and de Armas weren’t just any Hollywood couple.
They flaunted their relationship with matching heart necklaces, cozy oversized shirts, and public displays of affection that made headlines.
More importantly, Affleck’s family seemed to embrace Ana wholeheartedly.
His children—Violet, Fin, and Samuel—spent time with her, and even his ex-wife, Jennifer Garner, was said to approve.
Affleck’s younger brother, Casey, also had nothing but praise for Ana, calling her “the sweetest, funniest, smartest, most charming person.”
With so much support around them, it’s easy to see why Affleck might be questioning his past choices.
Public Scrutiny and Personal Battles
Affleck has spoken openly about his discomfort with media attention, something that became a significant factor in his relationship with Lopez.
In JLo’s 2024 documentary The Greatest Love Story Never Told, Affleck admitted he struggled with their highly publicized romance.
“Getting back together, I said, ‘One of the things I don’t want is a relationship on social media,’” Affleck revealed.
“But then I realized that’s not a fair thing to ask.”
Ana, too, struggled with the overwhelming spotlight that came with dating Affleck.
In a 2022 interview with Elle, she described the media frenzy as “horrible” and even cited it as a reason for leaving Los Angeles.
Moving Forward
Since their breakup, Ana has moved on from Affleck, dating Tinder executive Paul Boukadakis before their split last November.
More recently, she was spotted in Madrid kissing Manuel Anido Cuesta, the stepson of Cuba’s president, further fueling speculation about her love life.
As for Affleck? While his marriage to JLo may have ended, he reportedly still holds deep respect for Ana.
“He wishes he could go back and do things differently,” a source revealed.
“But it’s too late now. He just hopes she finds happiness.”
With both stars currently single, could fate bring them back together?
In Hollywood, anything is possible—but for now, they remain two people navigating life and love on separate paths.