Ben Affleck is reportedly ready to reconnect with Ana de Armas now that she’s ended her eight-month relationship with Tom Cruise, according to sources close to the 53-year-old Affleck. The breakup has reignited Affleck’s hope for a second chance with his former co-star, more than five years after their pandemic-era romance ended.
The situation carries extra tension because Affleck and Cruise were once friends. When Cruise, 64, began dating de Armas, 38, in early 2025, Affleck wasn’t pleased about the development. One source said Affleck is kind of a jealous type and that watching de Armas happy with a friend felt strange to him.
Affleck’s Friends Say He Never Got Over De Armas
The Oscar winner reportedly “hasn’t been able to forget” his former co-star, even during his rekindled romance and two-year marriage to Jennifer Lopez, 56. Sources claim Affleck continued to bring up de Armas throughout that period, suggesting the chemistry between them never fully disappeared for him.
Affleck and de Armas met on the set of the thriller “Deep Water,” which was filmed in early 2020 and released in 2022. Their relationship began around March 2020 and lasted until January 2021, with paparazzi frequently capturing them walking their dogs around Los Angeles during pandemic lockdowns. After they split, a cardboard cut-out of de Armas was famously photographed being tossed into a trash bin outside Affleck’s home — an image that quickly became internet legend.
Professional Envy Mixed With Personal Drama
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.
This isn’t the first time the two actors 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.
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.
Cruise Wasn’t Happy About Affleck’s Outreach
While Cruise and de Armas were still together, Affleck’s attempts to reconnect with his ex reportedly caused friction. Insiders claimed Cruise felt protective of the relationship and wasn’t keen on Affleck staying in touch 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.
The Cruise Romance Is Over
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, 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.
