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Throughout his acting career, Ben Affleck has dated a fair number of Hollywood stars. In the late 1990s, he dated Gwyneth Paltrow before becoming the other half of “Bennifer.” You may recall, he and Jennifer Lopez were dubbed the famous couple name after becoming a pair and later getting engaged in 2002. However, he ended up marrying another Jen. That is, Jennifer Garner after he and JLo announced the end of their engagement in 2004.
But after their tenth anniversary, the couple called it quits becoming the Oscar winner’s “biggest regret,” as he told the New York Times in an interview in February 2020. “Shame is really toxic. There is no positive byproduct of shame,” he said. “It’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing.”
Since then, the Gone Girl actor has gone on to date a few other ladies, including his latest love interest, Ana de Armas . Keep reading for a brief walk through Ben Affleck’s dating history.
© GettyImagesCheyenne Rothman
Ben’s high school sweetheart was Cheyenne, who he dated on and off for seven years until ending their relationship in 1997. The couple met as teens during summer camp – classic!
© GettyImagesGwyneth Paltrow
Ben began dating Gwyneth Paltrow later that year after they met at a dinner party hosted by Harvey Weinstein. The actors co-starred in Shakespeare in Love in 1998 but ended their relationship in 1999. However, there were still some sparks between them as they rekindled their romance while filming Bounce, but they officially called it quits in late 2000.
© GettyImagesJennifer Lopez
The Pearl Harbor star met Jennifer Lopez while on the set of Gigli. The A-listers got engaged in November 2002, following JLo’s divorce from Cris Judd in June of that year. “Bennifer,” you may recall, was all the rage as far as celebrity couples until they announced the end of their engagement in January 2004.
© GettyImagesJennifer Garner
The Town actor found love with another Jennifer – Jennifer Garner . Although they co-starred in 2001’s Pearl Harbor and 2003’s Daredevil, the Hollywood stars didn’t confirm their romance until October 2004. Ben and Jennifer went on to say ‘I do’ after getting engaged in April 2005 and later tying the knot in Turks & Caicos in June of that year.
Ten years later, after celebrating their anniversary, the Gone Girl actor and the 13 Going on 30 star announced their separation in June 2015. They finalized their divorce in October 2018.
The exes share three children, daughters Violet, who was born in December 2005, and Seraphina, who they welcomed in January 2009, and their son Samuel, born in February 2012.
© GettyImagesLindsay Shookus
Following his divorce, the father-of-three was seen with Lindsay Shookus, who he was reportedly dating since 2014, while married to Jennifer Garner. According to Us, sources confirmed that, “They were having a full-blown affair. They were sleeping together, sending each other cute texts and meeting up whenever they could.” It wasn’t until July 2017 that he and the Saturday Night Live producer went public with their romance.
The couple took their relationship to the next level after moving into a New York City apartment in November 2017. Nine months later, in August 2018, they went their separate ways and Ben briefly dated Shauna Sexton.
In February 2019, the Justice League actor reconciled his romance with Lindsay but officially called it quits that April.
© Grosby ImagesShauna Sexton
Ben and Shauna’s fling only lasted two months. The Playboy model and the Triple Frontier actor were spotted dining at Nobu in Malibu in August 2018 but reportedly ended their short romance after traveling together to Big Sky, Montana.
© GettyImagesAna de Armas
Ben is now dating Cuban actress Ana de Armas. The actors met while on the set of their upcoming film, Deep Water. Rumors of their romance first sparked in March 2020 when they traveled to Ana’s native Cuba. Soon after their affair made it to Costa Rica where they were spotted taking a romantic stroll on the beach. Soon after, their affair made it to Costa Rica, where they were spotted taking a romantic stroll on the beach. Since returning, the Knives Out actress and the Argo actor have been almost inseparable amid the quarantine.
