Ben Affleck's Relationship History, From Gwyneth Paltrow to Jennifer Lopez
Ben Affleck has had some highly-publicized romances during his time in the spotlight, but his list of ex-lovers is actually pretty short. While it's clear he has a thing for Jennifers (he's married two of them), he also has a habit of dating his costars. As of July 16, he's now married to Jennifer Lopez, who he first started dating over two decades ago when they met on the set of the movie "Gigli."
The pair broke off their first engagement in 2003, citing intense media attention as part of the reason why they called it quits, but the two restarted their relationship in May 2021 and finally tied the knot the year in an intimate Las Vegas ceremony, with Lopez showing off her gorgeous engagement ring and a gown from an "old movie" as she married her old flame.
As Affleck settles down with the newly-dubbed Jennifer Affleck, let's look back at the rest of his former flames over the years.
The short-film director was one of the first ladies to steal Ben's heart. The pair, who were high-school sweethearts, first met at summer camp and dated for about seven years before splitting in 1997, following the actor's rise to fame with "Good Will Hunting."
After splitting from his high-school sweetheart, Affleck started an A-list romance with Gwyneth Paltrow. The two dated off and on from 1997 to late 2000 and even shared the screen together in "Shakespeare in Love" and "Bounce," where they played love interests.
On the heels of his highly publicized split from J Lo, Affleck fell for yet another one of his costars on the set of "Daredevil." In 2005, the duo got married during a private ceremony in the Caribbean. They welcomed three children together, Violet, Seraphina, and Samuel, before announcing their separation in 2015. Nearly two years later, they officially filed for divorce, but have remained amicable exes as they coparent their children.
In July 2017, news broke that the "Justice League" actor was romancing Lindsay Shookus, a producer at "Saturday Night Live." While their relationship seemed fairly new at first, in 2017, Us Weekly reported that Affleck had actually been seeing Shookus on and off since 2015 while he was still married to Jennifer and she was married to former "SNL" colleague Kevin Miller. However, after their fair share of ups and downs, the couple split for good in April 2019.
Ana de Armas
Affleck then began dating his "Deep Water" costar in the spring of 2020. They were together for nearly a year before they split in January 2021. According to People, de Armas was the one who broke things off. "Their relationship was complicated," a source told the publication. "Ana doesn't want to be Los Angeles-based and Ben obviously has to, since his kids live in Los Angeles."
In 2002, Affleck started dating the "Jenny from the Block" singer after meeting on the set of their movie "Gigli." The pair, better known by their couple name Bennifer, became engaged a few months later in November when the actor popped the question with a $2.5 million diamond engagement ring. Less than a year later, their wedding was postponed because of "excessive media attention," which led to their breakup in January 2004.