The Gone Girl star hit the dating scene in showbiz as soon as he started rising in the ranks in the mid-1990s. Ben was romantically involved with Gwyneth Paltrow and the “Jenny From the Block” singer before falling in love with the 13 Going on 30 actress.
The handsome stud’s relationship with Jen turned out to be one of his most memorable to date. The former couple, who married in 2005, were together for more than 10 years and became the proud parents of their three kids, Violet, Seraphina and Samuel.
However, Ben and Jen called it quits and their divorce was eventually finalized in 2018. Fortunately, the Justice League actor and the Alias alum still share a fantastic relationship in order to amicably coparent their children.
Ben has since moved on from the Academy Award winner. After dating Lindsay Shookus and Shauna Sexton around 2018, he found love with his Deep Water costar Ana de Armas, who he met on the set of the thriller movie in late 2019.
“They’re playing a couple on the film, a husband and wife with some very dark secrets, and their chemistry is off the charts. They’ve become very close,” a source told In Touch Weekly in March 2020. “Ben loves that she’s originally from Cuba, he can’t get enough of her culture, and he loves her accent.”
Ben and Ana proved they were going strong as they were spotted on many outings together throughout 2020. The actor’s kiddos often accompanied the two as they made trips to the grocery store amid the coronavirus pandemic.
Just as things seemed to be going well, though, a separate source revealed the “dynamic [of their relationship] changed” when Ben and Ana “moved in together.”
In January 2021, another source confirmed the couple called it quits after nearly one year of dating. “Ana ended the relationship,” the insider divulged. “Ana still cares for Ben, but she can’t see a future with him. It wasn’t working and they weren’t on the same page.” While the former flames are “on amicable terms and still talk,” their relationship “is over.”
Scroll through the gallery below to see a complete timeline of Ben’s dating history through the years.
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