The Truth About Ben Affleck's Complicated Dating History

Fans of Ben Affleck may have been shocked to see him reunite with his ex-fiancée Jennifer Lopez in the summer of 2021. After all, it had been over 15 years since the former couple broke off their engagement (via Harper's Bazaar).

But the actor rekindling his romance with the singer is far from the only shocking moment in his complicated dating history. Did we ever think he'd divorce his seemingly-perfect wife, Jennifer Garner? The parents of three — they share kids Violet, Seraphina, and Samuel — were married in 2005 but split in 2018 (via PureWow and Insider).

Affleck has lamented his divorce, saying his family splintering was "painful and disappointing" and admitting, "I never thought I was gonna get divorced—I didn't wanna be a divorced person. I really didn't wanna be a split family with my children" (via Vanity Fair). The "Argo" star and director also called the divorce the biggest regret of his life (via Glamour).

Still, it seems the Oscar winner has moved on with Lopez — although she is not the first woman he dated post-split from Garner. And before his wife? Well let's just say there was a very famous faces he was photographed kissing.

Ben Affleck's early dating history included a fellow Oscar winner

Before his star was on the rise, the "Good Will Hunting" star dated Cheyenne Rothman, who Us Weekly says was his highschool sweetheart. The two parted ways right around the time Affleck's first film was released — and subsequently made him a household name (via IMDb).

Affleck would trade up for actress Gwyneth Paltrow, with the two becoming a couple to watch on the red carpet in 1997 (via E! Online). The gorgeous duo lasted until 2000, with the "Shakespeare in Love" star saying in 2003 about why things ended, "Ben makes life tough for himself. He's got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out."

After saying goodbye to his romance with Paltrow, Affleck moved on with none other than Lopez.

Bennifer the first time was larger than life

It was 2002, and Bennifer was as much a part of our culture as the other Jen — Aniston that is — and Brad Pitt (via Elle and Refinery29). The couple reportedly met while filming their box office bomb, "Gigli." The film was a flop, but the romance was hot, hot, hot, with the height of the frenzy surrounding their relationship being when Affleck appeared in the "Jenny from the Block" music video (via Esquire).

In November of that year, Affleck and Lopez got engaged (via Us Weekly). But in 2003, the couple claimed the media hysteria surrounding their "I do's" was too much, and ended up calling off the wedding. 

By 2004, they had called off their engagement all together, with Lopez explaining in 2010, "I love Ben. He's a great guy. But it was a lot for both of us to be under that type of siege for two years straight. Our relationship, I think, did suffer because of that" (via Cheatsheet).

Ben moved on after Jennifer Lopez

Of course, Affleck would go on to meet his wife, and marry her in 2005 (via Us Weekly). But the union dissolved in 2015, with the "Pearl Harbor" stars officially divorcing in 2018.

At that time, "The Town" star was already in a relationship with "SNL" producer Lindsay Shookus (via People). But their romance ended in 2018, just a year after they started dating, reportedly because Affleck, an alcoholic, went to rehab. The couple briefly reunited, only to go their separate ways for good in 2019.

Affleck was then linked to "Knives Out" actress Ana de Armas, but their romance ended after about a year in early 2021 according to People, with a source explaining, "She broke it off. Their relationship was complicated. Ana doesn't want to be Los Angeles based and Ben obviously has to since his kids live in Los Angeles."

Shortly after de Armas moved on, so did Affleck, and with, yup, you guessed it — Lopez.

Ben and Jen give it another go

Fans were delighted when Affleck and Lopez were spotted getting up close and personal in May of 2021 (via Elle). The superstars are now Instagram official, and have been taking their love all over the world, from Montana to Italy, with a source saying about the new and improved relationship, "She's crazy about Ben. He spoils her with love and is very witty and charming. He's a man's man, and she finds him so attractive and strong. She's in it for the long term and sees her future with him."

It's even been reported that Lopez is house shopping in Los Angeles so she can be close to Affleck, and that things are getting very serious again between the two celebs (via Hello! and Page Six).

Who knows what the future holds for the lovebirds, but maybe at last, Affleck can stop dating, and end up with his forever love with Lopez.