Ben Affleck’s romantic life has been a huge subject of interest for fans, and it should be: He’s always managed to surprise them. The Batman star is currently married to Jennifer Lopez after their second engagement in 20 years, and he was married to Jennifer Garner in between them. He also dated a bevy of big-name Hollywood beauties.
Learn more about Affleck’s dating history below.
Cheyenne Rothman
In high school, Affleck met Cheyenne Rothman, who would go on to be a film director herself. They dated while he was at Cambridge Rindge and Latin School in Cambridge, Massachusetts. They were together for seven years, and she attended the 1997 premiere of Chasing Amy with him. That was in March, and they reportedly broke up in the summer of that year.
A source told the Daily Mail, “She is the one who got away, but she’d had enough of Hollywood and everything that went with his fame. This is just speculation, but perhaps he wouldn’t be so unhappy if they’d stayed together. She was always really sweet and catnip to boys, but it just got too much for her. He did try to get her back after they split up [in summer 1997], but she didn’t want that lifestyle.”
Gwyneth Paltrow
Affleck and Paltrow were both cast in Bounce and Shakespeare in Love. They began dating soon after he split with Rothman. They were together on-and-off for about three years.
In 2015, Paltrow told Howard Stern, “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.”
She then shared her opinion on Affleck’s then-wife Jennifer Garner and their relationship.
“I like him,” she said. “He settled down, and his wife is awesome. Not only is she beautiful, she’s so warm, and she cooks and is so into her kids. She’s really great. I like her a lot.”
Jennifer Lopez
Affleck is currently married to actress and pop star Jennifer Lopez, but she also has the distinction of being his one-time ex-fiancée. The couple first met in 2002, starring in Gigli together. They were soon engaged and were supposed to be married, but postponed the wedding due to the “excessive media attention,” according to People. They split in 2004, and went on to have other relationships. J.Lo married musician Marc Anthony, with whom she had twins, Max and Emme. Affleck married Jennifer Garner (more on that ahead), and they had three children: Violet, Seraphina, and Samuel.
In May 2021, following their respective divorces, the pair was romantically linked once again after being spotted together in Montana. By July, Lopez was ready to go Instagram official and shared photos from her 52nd birthday that included Affleck. They were engaged in April 2022, then eloped in Las Vegas during July 2022. A month later, they had a more formal ceremony in Georgia on Affleck’s personal estate.
Jennifer Garner
In 2001, Affleck met Jennifer Garner while working on Pearl Harbor. They were then both cast in 2003’s Daredevil. The couple started dating soon after his breakup with Lopez and were married in June 2005. The two of them were married for 10 years, welcoming their three children.
In 2015, Page Six shared their joint statement announcing their separation.
“After much thought and careful consideration, we have made the difficult decision to divorce,” it read. “We go forward with love and friendship for one another and a commitment to co-parenting our children, whose privacy we ask to be respected during this difficult time. This will be our only comment on this private, family matter.”
The couple finalized their divorce in 2018 and have remained friends and good co-parents. Affleck has talked openly about how Garner supported him through treatment for alcohol addiction, and she accompanied him in 2018 when he entered rehab again.
In 2020, in an interview with the New York Times, Affleck talked about how drinking changed his relationship.
“Shame is really toxic,” he explained. “There is no positive byproduct of shame. It’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing.”
He continued, “I drank relatively normally for a long time. What happened was that I started drinking more and more when my marriage was falling apart. This was 2015, 2016. My drinking, of course, created more marital problems.”
Shortly after, he said on Good Morning America, “I didn’t want to get divorced, I didn’t want to be a divorced person, I really didn’t want to be a split family with my children. It upset me because it meant I wasn’t who I thought I was, and that was so painful and so disappointing.”
Lindsay Shookus
Affleck was linked to Saturday Night Live producer Lindsay Shookus in 2017. They split briefly in 2018 while he was in rehab before reuniting again. A source told Entertainment Tonight that they ultimately broke up in 2019 because of the differences in their schedules.
“The distance was definitely a huge factor in their breakup,” the insider said. “They both have a lot of love for each other but ultimately they realized it was not going to work.”
The source added that they have “so much love and admiration for each other.”
Ana de Armas
Affleck met actress Ana de Armas on the set of Deep Water in New Orleans in early 2020. The pair spent a lot of time together over the pandemic quarantine, but by January 2021, they had split up.
“Ben is no longer dating Ana,” a source told People. “She broke it off. Their relationship was complicated. Ana doesn’t want to be Los Angeles based, and Ben obviously has to since his kids live in Los Angeles.”
“This is something that was mutual and something that is completely amicable,” another insider shared. “They are in different points in their lives; there is deep love and respect there. Ben continues to want to work on himself. He has three jobs lined up and he’s a solid father at home. They are both happy with where they are in their lives.”
Aimée Lutkin is the weekend editor at ELLE.com. Her writing has appeared in Jezebel, Glamour, Marie Claire and more. Her first book, The Lonely Hunter, will be released by Dial Press in February 2022.
