Hollywood actor Ben Affleck’s dating history comes with a dash of high school romance, a sprinkle of rumoured cheating, and two Jennifer namesakes. 

From flings to engagements, here is a list of all the women ‘The Batman’ star has dated through the years.

Cheyenne Rothman

Rothman and Affleck were high school sweethearts who attended Cambridge Rindge and Latin High School in Cambridge, Massachusetts. While Affleck went on to become an actor with several Academy and Golden Globe Awards, his high school love ventured into filmmaking. 

Gwyneth Paltrow

Soon after his split with Rothman, the 49-year-old began dating actor Gwyneth Paltrow. The duo dated for three years and starred in ‘Shakespeare in Love’ and ‘Bounce’.

Jennifer Lopez

All along the way, Lopez was ‘the one’, even if it took Affleck 20 years and 2 engagements to realize it. The couple, known as Bennifer, began dating in 2002 and co-starred in ‘Gigli’ and ‘Jersey Girl’. 

Lopez and Affleck were set to tie the knot in Santa Barbara in 2003 but soon called it off after postponing.

Jennifer Garner

Affleck took the rebound concept to a whole new level by falling for yet another Jennifer, this time, actor Jennifer Garner. After meeting on the sets of ‘Pearl Harbour’, the couple tied the knot in 2005 and welcomed three kids into their family. 

The duo parted ways and finalized their divorce in 2018 as allegations of Affleck’s gambling and illicit romances arose.

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Lindsay Shookus

Shookus and Affleck briefly dated but broke it off in 2019 due to their “hectic schedules,” according to Entertainment Tonight. 

Shauna Sexton

In 2018, Affleck had a rumoured fling with Sexton, a former Playboy model who was over two decades younger than her beau. The fling came to an end after a few months. 

Ana de Armas

The duo met on the sets of ‘Deep Water’ in New Orleans and quickly became the talk of the town during the pandemic.

In January, the couple parted ways because they were in “different places” in their lives. “He would not commit to having more kids,” an insider told Page 6. “She is in her 30s. It was a deal-breaker.”

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Jennifer Lopez

After de Armas, Affleck quickly moved on to her former fiance and reportedly sent sappy love letters while Lopez was shooting for ‘Shotgun Wedding’. Fast forward to April 2022, the couple has gotten engaged, again.