More than five years after their January 2021 breakup, Ben Affleck is interested in reconnecting with Ana de Armas now that she has broken up with Tom Cruise, according to people familiar with the situation.
De Armas, 38, and Cruise, 64, ended their romance in October 2025 following an eight-month relationship. Sources say the 53-year-old Affleck has been watching developments closely and sees an opportunity to revive what they once shared.
The situation carries an extra layer of complication: Affleck and Cruise used to be friends. When the action star started seeing de Armas in early 2025, insiders say Affleck struggled with the pairing. According to one person close to the actor, jealousy played a role and the sight of his ex enjoying herself with someone in his social circle didn’t sit well.
The Spark That Never Fully Died
Affleck and de Armas began their relationship around March 2020 after meeting on the set of “Deep Water,” a thriller they filmed in late 2019 and early 2020 that hit theaters in 2022. Photographers captured them frequently during pandemic lockdowns as they walked dogs through Los Angeles neighborhoods.
Their romance lasted until January 2021. Shortly after the split, cameras caught a cardboard cutout of de Armas being thrown into a garbage bin outside Affleck’s residence, creating a viral moment online. According to insiders, the Oscar winner never fully moved on. One friend said he brought her up repeatedly even while married to Jennifer Lopez, 57, a union that lasted two years after they wed in 2022, separated in 2024, and finalized their divorce in early 2025. Those close to Affleck describe him as someone who “hasn’t been able to forget” what he shared with de Armas during that period.
Professional Envy and Personal Boundaries
The dynamic between Affleck and Cruise extends beyond romantic territory. Sources say Affleck has long felt a twinge of professional jealousy toward Cruise’s action-star success and substantial wealth. Yet the sentiment isn’t bitter, insiders clarify. Rather, Affleck respects that someone in his 60s continues commanding leading roles in massive films and aspires to similar career longevity.
Friends of Affleck have jokingly suggested he pursue Katie Holmes, Cruise’s ex-wife, as payback. Geography poses a barrier, though: Affleck resides in Los Angeles while Holmes lives in New York City, making the teasing suggestion impractical.
This isn’t the first overlap in their romantic histories. Affleck was involved with Gwyneth Paltrow intermittently from 1997 to 2000. Cruise shared a memorable on-screen kiss with Paltrow more than two decades ago, which she later recalled fondly, saying she “got to make out with Tom Cruise” and calling him an amazing kisser.
Tension During the Cruise-de Armas Romance
While de Armas was still with Cruise, Affleck’s attempts to maintain contact with her created friction. People familiar with the matter said Cruise “trusts Ana” but remained cautious about Affleck’s intentions.
Affleck wanted the kind of relaxed, platonic bond he maintains with his ex-wife, Jennifer Garner, sources explained. He and de Armas parted on good terms in January 2021 and agreed to keep in touch, but insiders say Affleck never felt he received proper closure. He values her friendship, particularly during times when loneliness has weighed on him.
The Current Landscape
Cruise and de Armas first appeared together publicly on Valentine’s Day 2025 at a London dinner. Their relationship became official knowledge over the summer, featuring private jet travel and upscale vacations. Around the time de Armas turned 37, a fan photographed the couple strolling through a London park, with the actress wearing a pale-pink T-shirt, skinny jeans, and carrying a Louis Vuitton cross-body bag while security walked alongside.
The couple ended their relationship in October 2025 after approximately eight months together. Reports indicated de Armas initiated the breakup because the relationship was progressing too fast and their age difference presented challenges, though they remained friends afterward. Since then, people close to Affleck say he’s prepared to pursue a second chance.
Affleck’s romantic life has drawn renewed attention following his 2025 divorce from Lopez. The actor, who has struggled with substance abuse issues and experienced a setback in 2019, is said to be in a more stable frame of mind now.
A single source told tabloid Globe that Affleck is “happy as can be” that de Armas is single again and intends to explore whether reconciliation is possible. Neither Affleck nor de Armas has made any public statements regarding whether she shares his interest, which remains unclear — insiders acknowledge she wasn’t pleased with how their initial relationship concluded. Still, those around Affleck say he’s willing to try, believing what they experienced together was exceptional. Since the breakup, the two actors have not commented publicly on these reports, and they have not gotten back together.