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Cheyenne Rothman

Ben and Cheyenne were high school sweethearts who began dating as students at Cambridge Rindge and Latin High School in Cambridge, Massachusetts, in 1990. The pair remained a couple until 1997, when the actor and screenwriter rocketed to fame.

Gwyneth Paltrow

The duo met at a party thrown by Harvey Weinstein in 1997 and soon started dating. Ben and Gwyneth would go on to star opposite each other in 1998’s Shakespeare in Love and again in 2000’s Bounce. They split after three years together.

The Goop founder discussed their relationship and breakup during a 2015 appearance on Howard Stern‘s Sirius XM show, saying, “I think [my parents] appreciated how he’s super intelligent and he’s really, really talented and so funny, but he was not in a good place in his life to have a girlfriend. I think they were OK with the two of us not being together.”

Jennifer Lopez (Round 1)

Ben and Jennifer fell for each other while filming the movie Gigli, even though she was still married to backup dancer Cris Judd at the time. The two divorced and “Bennifer” became one of Hollywood’s most talked about couples.

The two got engaged in November 2002 and were set to marry in September 2003 in an elaborate Santa Barbara, California, wedding. Ben and Jen called off the nuptials with just days to go and eventually broke up in January 2004.

“When Jen and I broke up before, the catalyst for that was the scrutiny around our private life,” Ben said in J. Lo’s 2024 documentary The Greatest Story Never Told.

The Maid in Manhattan star added, “We had a big wedding plan, three days before, we just crumbled under the pressure.”

Jennifer Garner

Ben met his second significant Jennifer when filming 2001’s Pearl Harbor and they starred opposite each other in 2003’s Daredevil.

The couple married in June 2005 while Jennifer was pregnant with the couple’s first child, daughter Violet. They went on to welcome two more kids, ​child Fin and ​son Samuel.

Ben and Jen split in 2015 amid his alleged infidelity with the family’s nanny. They divorced in 2018, but have remained close as coparents.

Lindsay Shookus

The Argo star began dating the Saturday Night Live producer in 2017, amid his split from Jen. They were together on-and-off for two years before splitting in 2019 due to conflicting work schedules.

Shauna Sexton

Ben was linked to the former Playboy model shortly before he entered rehab for alcohol addiction in August 2018. After he got out, the pair took a trip to Montana but ended things after two months together.

Ana de Armas

The two met while filming the psychological thriller Deep Water in New Orleans, Louisiana, in 2019. They began dating and confirmed their romance on a trip to her native Cuba in March 2020.

Ben and Ana spend the COVID-19 quarantine together in Los Angeles, but ultimately split in 2021.

Jennifer Lopez (Round 2)

Just weeks after J. Lo and fiancé Alex Rodriguez called it quits, she was spotted together with Ben on April 30, 2021, nearly two decades after calling off their romance.

The pair’s reunion resulted in an April 2022 engagement, followed by a July 2022 elopement in Las Vegas and a lavish formal wedding the following month at Ben’s estate in Georgia.

Ben and Jennifer began drifting apart during 2024, being photographed together less and less. He shocked fans not accompanying J. Lo to the Met Gala on May 6, 2024, as she was a co-chair of the event.

“The writing is on the wall – it’s over. They’re headed for a divorce – and for once, [Ben’s] not to blame!” a source told In Touch on May 15, one day after Jennifer was photographed house hunting in Beverly Hills solo. Ben and Jennifer purchased a $60 million mansion together in May 2023.

“Ben already moved out and they’ll likely have to sell the dream house they spent two years searching for,” the insider added. “They’ll never stop loving each other, but she can’t control him, and he can’t change her. There’s no way it could have lasted.”