Who Has Ben Affleck Dated? A Roundup of His Past Relationships Amid Jennifer Lopez Divorce

Cheyenne Rothman

Cheyenne Rothman was Ben’s high school sweetheart, whom he met when he was only a teen. He dated her on-and-off for over seven years before their official breakup came in 1997.

Gwyneth Paltrow

One of his most high-profile romances came early on with Gwyneth Paltrow. They were initially linked in 1997 after sparking a connection at a dinner party. The following year, they costarred in 1998’s Shakespeare in Love. They decided to end their relationship in 1999 but rekindled the flame briefly while working on the film Bounce. They broke up for the final time in 2000.

“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,” Gwyneth told Howard Stern during an interview in 2018 of her breakup from Ben.

Jennifer Lopez (Round 1)

Jennifer Lopez and Ben began dating after meeting on the set of the movie Gigli. In November 2002, Ben popped the question to the songstress. However, they did not make it down the aisle during their first go around. They ended up canceling their wedding in 2003 and calling off their engagement in early 2004.

Jennifer Garner

After his first breakup from J. Lo, Ben began dating Jennifer Garner, with whom he costarred in 2001’s Pearl Harbor and 2003’s Daredevil. They went public with their relationship in the fall of 2004, and he proposed in April of the following year. They welcomed three kids together after their 2005 nuptials, Violet, Fin and Samuel. In June 2015, Jen and Ben announced their separation and their divorce was finalized in October 2018.

Lindsay Shookus

Amid his split from Jennifer, Ben went public with his relationship with Lindsay Shookus in July 2017. He ended up moving in with the Saturday Night Live producer shortly after. The duo split in August 2018, and they briefly rekindled their romance in February 2019. However, it just wasn’t made to last, as they split for good in April 2019.

Shauna Sexton

During his break from Lindsay, Ben was seen out with Playboy model Shauna Sexton in August 2018. Their fling lasted two months.

Katie Cherry

Ben briefly dated Katie Cherry after meeting on the dating app Raya in 2019.

“He’s such a homebody,” she told In Touch in December 2021. “His favorite thing to do is sit at home, watch movies, have a chef cook something at home. He’s so normal and down to earth.”

Ana de Armas

Ben sparked a connection with costar Ana de Armas while working on the film Deep Water. They visited her native Cuba together in March 2020. One month later, they made their relationship Instagram official. After nearly a year together, they called it quits on their relationship in January 2021.

Jennifer Lopez (Round 2)

Following her split from Alex Rodriguez, Jennifer, who shares kids Emme and Max with ex-husband Marc Anthony, rekindled her romance with Ben two decades after calling off their wedding. They were seen spending time together in Montana in May 2021 and announced their engagement in April 2022. They got married in Las Vegas in July 2022 and had a bigger wedding in Georgia in August 2022.

Two years after their Georgia ceremony, Jennifer filed for divorce, listing their date of separation as April 26, 2024. Prior to the filing, the pair had been going through a rough patch in their relationship, which included Ben moving out of their shared marital home, In Touch first reported in May 2024. He later purchased a new home in July 2024 for $20 million without Jennifer, signaling that the end was near for the duo.