After bursting on to the Hollywood scene in the 80s and securing his heartthrob status, it didn’t take long for the actor to find himself in a high-profile romance with has been a Hollywood staple for decades, with many loving his versatile projects and getting any and every detail they can about his A-list-packed love life.
Speaking of his love life, Affleck has been in the news cycle for so long because of his flings, girlfriends, and wives.
Did you know that before he started dating Hollywood actresses, he was actually in a seven-year relationship with his high school sweetheart? Do you remember his short-lived flings in between his marriages?
We all know about his marriages with Jennifer Lopez, Jennifer Garner, and his relationship with Gwyneth Paltrow, but there’s so much more to his dating history than you may realize.
Below check out Affleck’s full dating history:
Cheyenne Rothman (1990-1997)
Cheyenne Rothman was Ben Affleck’s high school sweetheart. According to the Daily Mail, Affleck met Rothmann in 1990 at a Vermont summer camp while both were high school students at different schools in Boston.
The pair reportedly continued their romance while Rothman attended a private liberal arts college in Maine and Affleck headed for California after dropping out of the University of Vermont.
Rothman later relocated to Los Angeles to be closer to her up-and-coming actor boyfriend and even posed with him on the red carpet at the premiere of Affleck’s movie Chasing Amy in 1997. The couple broke up in the summer of 1997, before Affleck moved on with Gwyneth Paltrow. Rothman is now a married mom-of-three who lives her life out of the public eye.
Gwyneth Paltrow (1997-2000)
Ben Affleck and Gwyneth Paltrow met through Harvey Weinstein at Miramax’s pre-Academy Awards party in early 1997. They both appeared in Shakespeare in Love and by 1998, they were a couple.
In a 2015 interview with Howard Stern, via Vanity Fair, Paltrow hinted that their romance was troubled from early on. “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,” the Goop founder said.
The couple split briefly at the end of 1998 but reconciled when they were both cast in Bounce. They called things off for good in 2000. Paltrow seemed to looked back on the relationship fondly when she described his bedroom skills as “technically excellent” in a 2022 appearance on the Call Her Daddy podcast.
Jennifer Lopez (2002-2004)
In 2001, Jennifer Lopez and Affleck met while filming their 2003 rom-com flop Gigli. Their romance began in 2002 while Lopez was still legally married to Cris Judd. Her divorce was finalized in 2003.
In a 2016 interview with People, Lopez reflected on her first impressions of Affleck saying, “I really felt like when I met Ben, ‘Okay, this is it.’”
The couple’s relationship frequently made headlines, a reality Lopez poked fun at in her now-iconic “Jenny From The Block” music video which Affleck starred in. “We didn’t try to have a public relationship,” she said in 2016. “We just happened to be together at the birth of the tabloids.”
In November 2002, Affleck proposed to Lopez with a ring that reportedly cost $2.5 million. The engagement only increased scrutiny from the media, which Affleck reflected on in a 2021 podcast interview.
“People were so f—- mean about her — sexist, racist. Ugly, vicious s— was written about her in ways that if you wrote it now you would literally be fired for saying those things you said,” he said.
In September 2003, just three days before their scheduled nuptials, Affleck and Lopez called off their wedding.
“Due to the excessive media attention surrounding our wedding, we have decided to postpone the date,” the couple said in the statement. “When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realized that something was awry.”
Lopez’s reps later confirmed their split in January 2004.
Enza Sambataro (2004)
After splitting from Lopez, Affleck was briefly linked to TV ad sales exec and fellow Boston native Enza Sambataro, who went on to marry and later split from Red Sox player Kevin Youkilis.
“It wasn’t the most pleasant experience,” Sambataro told People about their relationship in 2004, adding that Affleck “tried to keep it very private,” but she decided “living that life is not me. I’d rather have my own sanity and private life.”
Jennifer Garner (2004-2015)
Affleck met his now-ex-wife Jennifer Garner in 2000 while filming Pearl Harbour, while Affleck was engaged to Lopez and Garner was married to Scott Foley. Their romantic relationship didn’t begin until 2004, when they were both single and working together on Daredevil.
After nine months of dating, Affleck proposed to Garner in April 2005. The couple quietly married in Turks and Caicos in June 2005, at which time their reps revealed Garner was pregnant with their first baby.
Their daughter, Violet Anne Affleck, was born on Dec. 1, 2005, followed by their second child, Seraphina Rose Elizabeth Affleck, on Jan. 6, 2009, and their son, Samuel Garner Affleck, on Feb. 27, 2012.
In a rare interview after 10 years together, Affleck gushed about his wife to Playboy in 2013. “She is by leaps and bounds the most important person to me in that respect,” the Oscar winner said. “Over the past 10 years she has allowed me to have a stable home life while accomplishing my professional goals.”
Amid reports about Affleck’s alleged infidelity and gambling, the couple announced their plans to divorce in June 2015.
Garner opened their split in a 2016 interview with Vanity Fair. “He’s the love of my life,” she said. “He’s the most brilliant person in any room, the most charismatic, the most generous. He’s just a complicated guy.” She also addressed rumors that he had an affair with the couple’s nanny and stated that she and Affleck were separated for months before the rumors came to light. “She had nothing to do with our decision to divorce,” she said.
The couple officially filed for divorce in 2017 while continuing to put on a united front. Garner publicly supported Affleck as he sought treatment for alcohol addiction, even driving him to rehab in 2018 shortly before finalizing their divorce.
The couple have remained on good terms and are regularly seen together with their children. “I’m very lucky she is the mother of my children. I’m very grateful and respectful of her,” Affleck said of his ex-wife in 2021.
Lindsay Shookus (2017-2019)
Affleck went public with his romance with Saturday Night Live producer Lindsay Shookus in 2017 but sources speculated the romance may have started as an affair as far back as 2013, while both were married. In 2017, a source claimed to People that Garner even confronted Shookus about the unconfirmed affair in 2015. “Lindsay refused to back down or quit the affair,” the source alleged.
Shookus revealed in a rare interview with Elle in June 2018 that she was finding all the attention on her amid her romance with Affleck “strange.”
“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,” she added. “Being considered a public figure honestly makes me laugh.”
Breakup rumors began to swirl in August 2018 when Affleck was spotted with model Shauna Sexton. However, the couple later reconciled in February 2019 before splitting for good a month later with a source claiming Affleck’s alchol relapse played a role.
“It was very hard for her to break up with Ben, but she knew he wasn’t getting better and that it was time for her to step aside,” a source told People. “She was trying to stay as close to him as possible so that he would stay on the right path, but ultimately it just wasn’t possible. She knew she had to let him hit bottom.”
Shauna Sexton (2018)
Affleck was briefly linked to Playboy model Shauna Sexton when the pair were spotted getting dinner in Malibu in August 2018, according to Us Weekly. The following month, Sexton was photographed driving Affleck’s car to a treatment facility in Los Angeles, where the Argo director was seeking help for his addiction issues.
In October, Sexton posted a photo of Affleck on Instagram while the pair were enjoying a getaway in Montana. However, days later Affleck returned to rehab and sources claimed to People that the duo were no longer seeing each other and that the fling was never serious.
Sexton later hit back at trolls blaming her for Affleck’s relapse in her Instagram comments. She wrote: “He makes his own decisions. Blaming a 22 year old for someone’s 3rd time in rehab is just ridiculous.”
Katie Cherry (2019)
Affleck briefly dated musician Katie Cherry in 2019. The relationship was first confirmed by Us Weekly in October but Cherry later revealed that they first met online, through the dating app Raya, in June.
“We FaceTimed for four months before we met. It wasn’t every day, but it was every once in a while,” she told InTouch in 2021. She confirmed that they dated for about 3 months after finally meeting in person in October but it fizzled out.
Ana de Armas (2019-2021)
Affleck met Ana de Armas while filming their psychological thriller Deep Water in late 2019. Their romance was confirmed in March 2020 when they were spotted on a romantic getaway in Cuba, a month before de Armas made their romance Instagram official.
Their romance appeared to be thriving when a source spoke to Us Weekly in May 2020, saying, “They are having so much fun together, and she has been telling her friends how Ben is the most amazing boyfriend she’s ever had.”
In August 2020, rumors swirled that the couple were moving in together and People reported that de Armas was getting close with Affleck’s kids. However, in January 2021, People confirmed the couple’s split.
“Ben is no longer dating Ana,” a source told the outlet. “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.”
In a 2022 interview with Elle, de Armas called the media attention on the relationship “horrible” and revealed that it was one of the reasons she moved out of LA.
Jennifer Lopez (2021-)
Fresh off his breakup with de Armas, Affleck reportedly got back in touch with ex-fiancée Jennifer Lopez via email, according to Page Six, while her relationship with Alex Rodriguez was winding down. In May 2021, rumors about a rekindled romance swirled when the couple were spotted together in Montana.
Lopez confirmed the reconciliation in July 2021 when she posted a photo of her and Affleck kissing on Instagram before stepping out for their first red carpet together in two decades at the Venice Film Festival in September.
“It’s a beautiful love story that we got a second chance,” Lopez told People in February 2022. In April 2022, Affleck and Lopez got engaged for the second time and married in a small Las Vegas ceremony three months later before hosting a larger ceremony in Georgia that August.
“Some old wounds were healed that day and the weight of the past finally lifted off our shoulders. Full-circle — and not at all the way we planned it. Better,” Lopez wrote in a newsletter after the wedding. “This was the perfect timing.”
Affleck praised Lopez’s career in a rare comment about his wife in a March 2023 interview with The Hollywood Reporter, saying: “Oh my God, she’s brilliant. She is incredibly knowledgeable about the way fashion evolves through the culture as a confluence of music, sports, entertainment and dance.”
However, in May 2024, reports about the couple’s marital troubles began to swirl. “They started having issues a few months ago as Jen had started ramping up work commitments and prepping for her tour,” Us Weekly reported at the time. “They are on two completely different pages most of the time.”
While the couple has no addressed rumors, it was reported that Affleck has moved out of their shared home and is living in a separate property.
