Ben Affleck’s Dating History — From Jennifer Lopez to Jennifer Garner and More

High school sweethearts Ben Affleck and Cheyenne Rothman met as teens at summer camp before they developed a romance. The pair went on to date for over seven years until they split in 1997.

Gwyneth Paltrow became Affleck’s new lady after breaking up with his high school sweetheart. They met at a 1997 dinner hosted by Harvey Weinstein.

They dated and worked together on several projects until they called it quits in 1999. However, they scored a second chance when they reunited in the film Bounce, but they broke up for good in 2000.

Affleck proved that love is sweeter the second time around with Jennifer Lopez.

They worked together in the film Gigli and immediately sparked romance rumors after Lopez divorced Cris Judd. The couple got engaged in November of the same year and started planning their marriage.

However, due to extreme media attention and negative scrutiny that affected their relationship, they called off their engagement and moved on with different people.

Nearly two decades after their failed engagement, they made their way back into each other and started dating again in 2021. Affleck popped the question again in April 2022 and finally wed the “On the Floor” singer in July 2022.

Affleck worked with Jennifer Garner in Pearl Harbor and Daredevil in 2001 and 2003, respectively. Although romance rumors immediately rose, their relationship was not confirmed until 2004.

The Batman v Superman star proposed to her in April 2005 and officially tied the knot in June 2005. During their relationship, they welcomed three children together: Violet, Seraphina and Samuel.

However, they ended their marriage in June 2015 and finalized their divorce in October 2018.

Amid Affleck’s marriage with Garner, the Justice League star reportedly had a “full-blown affair” with Lindsay Shookus. They kept their relationship a secret until July 2017 before taking everything to the next level by moving in together into a New York City apartment.

According to sources, they slept together and met up when they could, despite Affleck being married.

Their relationship did not last, as they broke up in August 2018. They tried again in February 2019 but ended things for good two months later.

In August 2018, Affleck was spotted with Shauna Sexton at Nobu in Malibu. Reports said they were together for two months before splitting following a trip to Big Sky, Mont.

After meeting on Raya – a dating app – the Gone Girl star briefly dated Katie Cherry.

In March 2020, sources confirmed that Affleck was dating his Deep Water costar Ana de Armas following the duo’s romantic vacation in Cuba. He was reportedly serious about her, as he wanted his kids to get to know more about the Knock Knock star.

However, they amicably split in January 2021.