Cheyenne Rothman (199? – 1997)
Ben Affleck dated his high school sweetheart Cheyenne Rothman until 1997. The two walked the red carpet of Chasing Amy, but the couple didn’t last that long.
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Ben Affleck’s dating life has always been in the spotlight. Even in those broody paparazzi pictures, he always had someone to rely on—well until his divorce from Jennifer Lopez that is.
The Batman vs. Superman actor had dated and married a bunch of A-List celebrities, but no one can outperform the way that Bennifer had a grip on celebrity dating news. J-Lo reflected on being in the spotlight during the first iteration of their relationship “Our relationship crumbled under the weight of the pressure,” Lopez told Variety. “We lost a sense of ourselves, and we needed to separate because we didn’t know how to survive it. I had to figure myself out, and he had to figure himself out.”
Ben Affleck is currently single. But let’s take a look at his complete dating history below.
Ben Affleck dated his high school sweetheart Cheyenne Rothman until 1997. The two walked the red carpet of Chasing Amy, but the couple didn’t last that long.
Gwyneth Paltrow and Ben Affleck dated after she was introduced to him by Harvey Weinstein at a party. The two later starred in Shakespeare in Love together in 1998. They called it quits in 1999 but briefly reunited in 2000. 18 years later, the Iron Man actress reflected to Howard Stern about the relationship. “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 okay with the two of us not being together.”
Bennifer is probably Ben Affleck’s most publicized relationship. They started their relationship in 2003 after they met on the set of Gigil. The two got engaged but they called it quits in 2004
However, things got back on track when Ben and Jennifer reunited in 2021 after sixteen years apart. The pair rekindled their relationship in April 2021 following J-Lo’s split from Alex Rodriguez, whom she broke up with after four years together. At this time, Ben was already divorced from his ex-wife Jennifer Garner. They were together from 2005 to 2018.
J-Lo and Ben had their second wedding at his estate in Riceboro, Georgia. The wedding was held on the weekend of August 19, 2022. According to Page Six, the second wedding was held for three days. There was a rehearsal dinner on Friday, and the actual ceremony took place on Saturday. On Sunday, the wedding concluded with a barbecue and picnic on Sunday.
In 2024, after months of speculation (first reported by In Touch in May), TMZ confirmed that J-Lo and Affleck had filed for divorce—on the second anniversary of that lavish ceremony in Georgia, no less. “She’s lost everything. Between dealing with crisis management and intense heartbreak, she’s told friends she needs help,” an insider told In Touch Weekly, adding that JLo was “humiliated that it’s over already after just two years. She’s been crying all the time, going from anger to despair to delusion, and even having panic attacks. She’s saying she can’t imagine a scenario where she can exist without Ben in her life, which is putting a ton of pressure on him.”
Related: Read more about Jennifer Lopez’s dating history before Ben Affleck
Ben Affleck was in a relationship with Jennifer Garner from 2005 to 2015. The couple first met on the set of the 2001 film Pearl Harbor. They became close friends after co-starring in Daredevil, but Garner was married to Scott Foley and Affleck was engaged to Jennifer Lopez.
They reunited in 2004 and dated for nine months. Affleck popped the question on Garner’s 33rd birthday in April 2005 and married on June 29, 2005. The couple have three children together, Violet Anne (born 2005), Seraphina Rose Elizabeth Affleck (born 2009), and Samuel Garner Affleck (born 2012).
Garner and Affleck announced their divorce days after their 10th anniversary. “After much thought and careful consideration, we have made the difficult decision to divorce,” the couple said in a joint statement at the time. “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. Thank you for understanding.” Their divorce was finalized in October 2018, about three years after they initially called it quits.
Related: Check out Jennifer Garner’s dating history and who she’s dating after Ben Affleck
Jennifer Garner is currently dating John Miller. In Jan. 2026, The National Enquirer reported that Garner and Affleck’s closeness has been taking a toll on their relationship. “John has been incredibly patient, but there’s no denying that it’s getting harder to ignore her dynamic with Ben,” a source tells the National Enquirer. “Jen’s promised so many times that things are going to be different and they have improved to a point, but unfortunately, her relationship with John does take a back seat way more often than it should.”
“John loves Jen and respects how seriously she takes co-parenting,” insists the source. “He understands that her kids will always come first and he’s OK with that. What he’s not happy about is feeling like he’s coming second to her ex-husband.”
Ben Affleck dated Lindsay Shookus after he appeared on Saturday Night Live in 2013. Shookus is a producer on the sketch comedy show and the two made it official in 2017 after they looked cozy a couple years prior.
On being with an A-List actor, Shookus reflected to Elle, “It’s strange to me,” she says. “My entire career has been behind the camera, and that’s definitely where I’m most comfortable. I’m a producer, I’m a mom, a friend. Being considered a public figure honestly makes me laugh.”
The two broke up in 2018, a year after becoming official, but briefly reunited in 2019.
While Affleck and Shookus were on a break, Affleck was seen going on dates with former Playboy model and veterinarian tech Shauna Sexton. While they were dating, Affleck re-entered rehab for the third time. Affleck fans blamed her for getting the actor “thrown back” into rehab.
“He makes his own decisions. Blaming a 22-year-old for someone’s 3rd time in rehab is just ridiculous. He is human. I am human,” she wrote on an Instagram post at the time. The two broke up after they went on a short trip to Montana.
Ben and Ana reportedly met on the set of the 2021 film Deep Horizon in early 2020. News broke of their relationship in March 2020 after they were photographed on vacation together in Cuba and Costa Rica. By January 2021, however, multiple sources confirmed that their relationship was over. According to one insider, who spoke to People, Ana was the one to break things off. “Ben is no longer dating Ana,” the source said at the time of the breakup. “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.” Who can forget Ben throwing away his Ana de Armas cardboard cutout during the height of COVID Lockdowns?
Ben Affleck was linked with Kick Kennedy, the daughter of Robert F. Kennedy Jr. Sources told People that the two were seeing each other. “Kick and Ben have been spending time together, but I’m not sure what’s happening,” one source told the publication. “Kick’s celeb crush has always been Ben.”
However, another insider said that the two might not even be hanging out with People, “I don’t think they even know each other. There’s definitely nothing going on.” Sources told TMZ that the relationship is strictly platonic and that Kennedy just “thinks highly of Ben.” But the two have been spotted in celeb hot spots like Beverly Hills Hotel’s Polo Lounge, according to Page Six. So only time could tell whether these two will head toward a romantic relationship.
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