Ana de Armas has split from Tom Cruise after the two dated for eight months, and her ex-boyfriend Ben Affleck has reportedly taken notice. Sources close to the 53-year-old Affleck say he’s hoping the newly single de Armas might give their old romance a second chance, more than five years after they parted ways.
The twist? Affleck and Cruise are former friends, which made the whole situation a little awkward from the start. When Cruise, 64, began dating de Armas, 38, in early 2025, word got around that Affleck wasn’t exactly thrilled. One source said Affleck is kind of a jealous type and that watching de Armas happy with a friend felt strange to him.
How Ben and Ana First Connected
Ben Affleck and Ana de Armas first met while working together on the thriller “Deep Water,” which was filmed in early 2020 and released in 2022.
The pair began dating around March 2020, and their relationship quickly drew attention during the pandemic lockdowns — paparazzi frequently captured them walking their dogs around Los Angeles. They dated until January 2021 before calling it quits. Soon after the breakup, a cardboard cut-out of de Armas was famously seen being tossed into a trash bin outside Affleck’s home — an image that quickly became internet legend. Sources say the chemistry between the pair never fully faded for Affleck. One friend claimed he continued to bring up de Armas even during his rekindled romance and two-year marriage to Jennifer Lopez, 56. The Oscar winner reportedly “hasn’t been able to forget” his former co-star, and the pandemic-era spark left a lasting impression.
A Friendly Rivalry With Cruise
Beyond the romance angle, there’s a professional undercurrent to the story too. Affleck has reportedly always harbored a little envy over Cruise’s blockbuster action career and mega-wealth. But the same source insisted the feeling isn’t malicious. The same insider said Affleck genuinely admires that a colleague in his sixties is still headlining major films and hopes to enjoy that kind of longevity himself one day.
Affleck’s pals reportedly joked that he should get revenge on Cruise by dating the actor’s ex-wife, Katie Holmes. The problem is purely logistical: Affleck lives in Los Angeles, while Holmes calls New York City home. As friendly ribbing goes, it’s a fun idea that would be tough to pull off across the country.
Interestingly, this isn’t the first time Affleck and Cruise have shared a connection to the same woman. Affleck dated Gwyneth Paltrow on and off from 1997 to 2000. Cruise, meanwhile, shared a memorable on-screen kiss with the Oscar winner more than two decades ago. Paltrow once recalled that she “got to make out with Tom Cruise” and called him an amazing kisser.
Cruise Reportedly Guarded His Territory
While Cruise and de Armas were still together, Affleck’s outreach to his ex reportedly ruffled some feathers. Insiders claimed Cruise felt protective of the relationship and wasn’t keen on Affleck reconnecting with de Armas. One source said Cruise “trusts Ana” but keeps a wary eye on Affleck.
The tension, sources say, stemmed from Affleck wanting an easy, open friendship with de Armas — similar to the one he shares with his ex-wife, Jennifer Garner. Insiders suggested Affleck and de Armas ended their relationship on friendly terms and vowed to stay in touch, though Affleck reportedly admitted he never got real closure after the split. He’s said to value her friendship, especially during a period when he’s been feeling lonely.
Where Things Stand Now
De Armas and Cruise were first publicly linked on Valentine’s Day 2025, when the pair were photographed at dinner in London. Their romance went public over the summer, complete with private jet trips and luxury getaways. Around the time of de Armas’ 37th birthday, the pair were captured by a fan on a sunny walk through a London park — she wore a pale-pink T-shirt with skinny jeans and carried a Louis Vuitton cross-body bag, flanked by security.
But the relationship has since fizzled. With de Armas back on the market, Affleck’s friends say he’s ready to make a move. His personal life has been under fresh scrutiny since he ended his whirlwind two-year marriage to Lopez in 2024; the pair had married in 2022 and officially separated in 2024. They finalized their divorce in early 2025. Affleck, who has battled alcohol addiction and relapsed in 2019, is reportedly in a more grounded place these days.
According to a source who spoke to Globe, Affleck is “happy as can be” that de Armas is single again and is planning to test the waters for a reunion. Whether she feels the same way remains to be seen — insiders acknowledge de Armas wasn’t thrilled with how their relationship ended. Still, those close to Affleck say he’s willing to take the risk, convinced that what they had was something rare. For now, all eyes are on whether this Hollywood do-over ever gets off the ground.
