Ben Affleck revealed his biggest dating mistake decades before his divorces

It’s no secret that Ben Affleck has gone through it when it comes to relationships. After headline-making breakups and two failed marriages, reports suggest that he may be thinking about dating again. If he does find someone he’s interested in, his own words from decades ago may help him avoid one of his biggest relationship flaws.

Affleck hasn’t been linked to anyone since his divorce from Jennifer Lopez in 2024. But according to Page Six, while the Air director isn’t rushing into anything serious, he is “open to putting himself out there again.” 

The A-Lister’s relationship history includes high-profile romances with stars like Gwyneth Paltrow, Jennifer Garner, Ana de Armas.

And one interview from the late ’90s may offer some insight into why so many of those relationships struggled.

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Back in 1999, Affleck sat down with Playboy and made a surprisingly candid confession while discussing his breakup with Paltrow. After explaining that they were able to stay friends after the breakup, Affleck admitted that it probably wouldn’t be possible with his other ex-girlfriends. “Mostly, yeah,” he said when asked whether former girlfriends were angry with him.

He then assessed his behavior in relationships. According to Affleck, the problem wasn’t cheating or mistreatment. He said his biggest issue was staying quiet when things bothered him and letting it boil over. “If you get dissatisfied and unhappy and don’t say something, if you don’t deal with it right then, it just festers and stays there,” he explained.

Rather than confronting problems head-on and saying, “‘Look, don’t do that, please don’t act this way,'” he said he would “go along with it until I just don’t want to be in the relationship at all.” The Hypnotic star said he would then “create some incident or do something or just don’t call. And then she’s pissed.”

“And I can’t necessarily blame her at that point since I’ve developed such a passive-aggressive rage that I have no sympathy and tell her, ‘Well, of course I didn’t call you. If you weren’t such a nagging, shrewish harpy I’d call you,'” he continued. “But that hopefully is something I’m growing out of.”

Affleck’s major relationships

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Affleck went on to marry Garner in 2005, before divorcing in 2018. Despite the split, they’ve built one of Hollywood’s strongest co-parenting relationships as they support their children, Violet, Seraphina, and Samuel.

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He was then linked to de Armas from 2020 to 2021. According to reports at the time, the pair wanted different things for their future, and it was amicable.

Then came his round two moment with Lopez. After calling off their first engagement in the early 2000s, Bennifer 2.0 reunited and walked down the aisle twice in 2022. She went on to file for divorce on their second wedding anniversary. 

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Now, Affleck has been looking healthy, happy, and focused on work and family. With reports that he may be ready to date again, a source told Page Six, one of his ex-wives would like to see him put a pause on dating. 

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A source told Page Six that Garner believes he is in a good place and should keep focusing on himself.  “She cares about him a lot and only wants what’s best for him at the end of the day,” the insider said.