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If you spent any part of 2020 scrolling through Twitter, you remember the dog walks. The iced coffees. The constant, almost daily paparazzi shots of two people who looked like they were in a perpetual rom-com. Ana de Armas y Ben Affleck were the unofficial mascots of the lockdown era.
It was a strange time for everyone. We were stuck inside, and they were outside, maskless and grinning. Honestly, their relationship felt like a fever dream. One minute they’re filming an erotic thriller in New Orleans, and the next, there’s a life-sized cardboard cutout of Ana being shoved into a trash can by a guy who looked suspiciously like Casey Affleck.
The Deep Water Spark
It all started on the set of Deep Water. It’s a movie that, quite frankly, was delayed so many times people forgot it existed until it finally hit Hulu in 2022. But back in late 2019, the chemistry was immediate. Sources from the set mentioned they were 100% professional, yet the spark was undeniable.
They weren't just "co-stars." By March 2020, they were spotted in Havana, Ana’s hometown. Then Costa Rica. Then the world shut down, and they hunkered down together in Los Angeles.
For nearly a year, they were inseparable.
Why the "Ana de Armas y Ben Affleck" Romance Actually Ended
People love to speculate about why Hollywood couples split. Was it cheating? Was it a PR stunt? For Ana and Ben, the reality was much more grounded—and slightly sadder.
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Ana didn’t want to be tied to Los Angeles. She’s a global star. At the time, her career was exploding with Knives Out and No Time to Die. She wanted to travel, to live in New York, to see the world. Ben, on the other hand, is a father first. His three kids—Violet, Seraphina, and Samuel—live in LA with Jennifer Garner. He wasn't going to leave them.
It was a classic "different life stages" situation. He was 48, she was 32. He wanted stability; she wanted to fly.
Then there was the pressure. Ana later admitted that the constant paparazzi attention in LA was "horrible." She couldn't walk her dogs without a dozen lenses in her face. It became a cage. By January 2021, they called it quits over the phone.
The Cardboard Cutout: Fact vs. Fiction
We have to talk about the trash can.
Shortly after the breakup, photos went viral of a man—wearing a mask and a hoodie—stuffing a life-sized cardboard cutout of Ana into Ben’s garbage bin. The internet lost its mind. Was it Casey Affleck?
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Casey actually went on the record with Entertainment Tonight to deny it. He said, "No, that's not me." He even praised Ana, calling her the "sweetest, funniest, smartest person."
The truth is the cutout was a prank. Ben’s kids had used it to play a joke on their dad over the summer. When the relationship ended, the joke ended, too. It wasn't a malicious act of "throwing her away," but in the context of a public breakup, it looked absolutely brutal.
Where Are They Now in 2026?
A lot has changed since those 2020 dog walks.
Ben famously went back to Jennifer Lopez, got married, and then—as of the most recent reports in 2025 and 2026—faced another high-profile divorce. He’s been spotted lately looking contemplative in Brentwood. There are even whispers in the tabloids that he’s "happy she’s back on the market" now that Ana has reportedly split from her own recent partners.
Ana, meanwhile, moved to New York just like she wanted. She’s become a Louis Vuitton ambassador and a heavy hitter in the awards circuit. Most recently, she stunned at the 2026 Golden Globes in a sheer lace dress that proved she’s moved far beyond the "Ben's girlfriend" label.
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What We Can Learn From the "Benana" Era
Relationships born in a crisis—like a global pandemic—often have an expiration date. When the world is small, you only need each other. When the world opens back up, you realize your paths don't actually align.
If you're looking for lessons from the Ana de Armas y Ben Affleck saga, here are the real takeaways:
- Geography is a dealbreaker: You can love someone deeply, but if your lives are rooted in different cities, the friction will eventually win.
- Privacy is a luxury: High-profile romances under a microscope rarely survive the heat.
- Don't buy a cardboard cutout of your partner: It never ends well.
Keep an eye on the trades. With both of them currently navigating the single life in 2026, Hollywood's obsession with "round two" stories is only just beginning. But for now, they remain a perfect, grainy, iced-coffee-stained memory of a very specific moment in time.
Check out Ana’s recent filmography to see how her acting style evolved post-2021, and keep a tab on Ben’s upcoming production slate with Artists Equity—he's currently focusing more on the director's chair than the paparazzi lens.