When it comes to relationships in the spotlight, things can get messy. And for Ben Affleck and Ana de Armas, the end of their romance certainly didn’t leave much to the imagination.
In a now-infamous moment, a life-sized cardboard cutout of Ana was discarded in front of Affleck’s Los Angeles home, marking the dramatic end of their relationship.
How Their Romance Started
Affleck and Armas first crossed paths in 2019 on the set of Deep Water, an erotic thriller where they played a married couple.
The chemistry between them wasn’t just for the cameras.
By March 2020, their on-screen connection had sparked a real-life romance.
They were soon seen vacationing together, and by April, they made things official on Instagram.
As the world went into lockdown due to the COVID-19 pandemic, the couple found themselves quarantining together at Affleck’s $19 million mansion in Pacific Palisades.
With plenty of time on their hands, they grew closer, spending their days ordering takeout and taking walks with their dogs in the upscale neighborhood.
According to a source, “Ben and Ana had such a special and unique relationship because they were holed up together 24/7 during the pandemic.
They got so close so fast, and it was passionate and real.”
But, like many pandemic relationships, this one didn’t last.
The Breakup and Quick Transition
Fast forward to 2022, and the love story had already unraveled.
Two years after their breakup, the paparazzi caught Affleck throwing away Ana’s cardboard cutout in a rather dramatic move.
By this time, he had quickly moved on to rekindling his romance with Jennifer Lopez.
Affleck and Lopez’s whirlwind romance made headlines in the early 2000s, but their first engagement fell apart in 2004.
Yet, after just a few months of reuniting, the couple married in a Las Vegas ceremony in July 2022.
However, their second attempt at love was also short-lived. Last August, JLo filed for divorce.
Affleck’s Regret: The Ana De Armas Dilemma
So, what went wrong? Sources close to the situation claim that Affleck’s relationship with Armas ended because she wanted marriage, but he wasn’t ready to commit.
Now, with a bit of distance from the situation, it seems Affleck regrets his decision.
At 52, Affleck is said to be looking back at his time with Armas, realizing that he might have dodged a bullet with JLo if he had stuck with the Cuban actress.
A source says, “He knows how she must have felt.” In fact, he may be feeling the sting of jealousy as rumors swirl about a potential romance between Armas and none other than Tom Cruise, who is nearly twice her age.
Their Love Was Real—And So Was Their Support System
Throughout their relationship, it was clear that Ana had earned the approval of Affleck’s family.
His children—Violet, 19, Fin, 16, and Samuel, 13—took to her right away.
They even spent a family vacation together at Affleck’s $7.1 million estate in Georgia, where Armas’ dog Elvis joined the fun.
Ben’s brother, Casey Affleck, also spoke highly of Ana after their split, calling her “the sweetest, funniest, smartest, most charming person.”
Even Jennifer Garner, Affleck’s ex-wife and the mother of his children, was said to approve of her.
Public Life and Private Struggles
Both Ben and Ana have struggled with the intense public attention that comes with being in the limelight.
During the 2024 documentary The Greatest Love Story Never Told, Ben admitted that he wasn’t entirely comfortable with the social media aspect of his relationship with JLo.
“I said, ‘Listen, one of the things I don’t want is a relationship on social media,’” he shared.
While Lopez understood his discomfort, she also acknowledged that she wasn’t going to stop being herself just because of his unease.
Ana also felt the pressure of the spotlight after her split from Ben.
She admitted in an interview with Elle in 2022 that the attention was “horrible” and that it was one of the reasons she left Los Angeles.
“This is not the place for me to be. It became a little bit too much. There’s no way out,” she said.
Looking Ahead: What’s Next for Ben and Ana?
Despite the regrets, it seems that the chance for a reconciliation is gone.
A source shared that while Ben wishes he could go back and do things differently, he knows it’s too late now.
He has much respect for Ana and hopes she finds happiness, including the family she wants.
As for Ana, she didn’t take long to heal from the breakup. Within six months, she started a relationship with Tinder exec Paul Boukadakis, but that ended in November 2023.
She was recently seen kissing Manuel Anido Cuesta, the stepson of Cuba’s president, and rumors have also circulated about her and Tom Cruise.
But for now, it appears both are on the market, with no official relationship status with anyone else.
It’s a messy tale of love, regret, and public scrutiny. But for Ben Affleck, the question remains: could he have had it all with Ana? Or was his next chapter with JLo just part of his own journey?