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Today β€” 9 January 2025Main stream
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Ben Affleck’s Dating History Through the Years

βœ‡Us Weekly News
By: Dory Jackson
6 January 2025 at 17:10

Ben Affleck is no stranger to a high-profile romance β€” but not all of them have ended happily ever after.

Over the years, the Justice League actor has proven that he can still be on good terms with an ex despite breaking up. In a February 2020 New York Times profile, he showed his support for ex-fiancΓ©e Jennifer Lopez after her 2020 Academy Awards snub for her work in Hustlers.

β€œShe should have been nominated. She’s the real thing. I keep in touch periodically with her and have a lot of respect for her,” he told the publication at the time. β€œHow awesome is it that she had her biggest hit movie at 50? That’s f–king baller.”

In May 2021, Us Weekly confirmed the pair were back together after splitting more than a decade earlier. In April 2022, Lopez confirmed that the couple were officially engaged for the second time. Three months later, the pair tied the knot in Las Vegas. Us confirmed in August 2024 that Lopez filed for divorce from Affleck after two years of marriage. They finalized their divorce in January the following year.

Scroll down to see Affleck’s greatest loves and flings throughout the years.

Β© David Fisher/Shutterstock; Jim Smeal/BEI/Shutterstock

Β© Newscom/MEGA

Rothman was Affleck’s high school sweetheart. After meeting as teens at summer camp, the duo dated on-and-off for over seven years until ending their romance in 1997.

Β© Alex Berliner/BEI/Shutterstock

Affleck met Paltrow at a dinner hosted by Harvey Weinstein back in 1997 and they began dating later that year. From there, the A-listers costarred in 1998’s Shakespeare In Love but called it quits in 1999. They rekindled their relationship while filming Bounce, but called off their romance a second time in late 2000.

Β© Richard Young/Shutterstock

Affleck met Lopez on the set of their film Gigli. Following the finalization of Lopez’s divorce from Cris Judd in June 2002, she and Affleck got engaged that November. The Gone Girl actor and β€œOn the Floor” singer, who earned the power couple name of β€œBennifer” during their romance, announced the end to their engagement in January 2004.
Nearly two decades later, the pair reunited following Lopez's split from Alex Rodriguez. They spent a weekend together in Montana in May 2021, and a source told Us that they have β€œalways loved each other." After the duo were spotted kissing at a gym during a romantic getaway to Miami, a source confirmed to Us that they were back together.
"Ben and Jen feel so close to each other very quickly," the insider shared. "The old flame is absolutely rekindled. They picked up where they left off in terms of affection for each other." In April 2022, Lopez officially confirmed that the couple were engaged again for the second time. Us confirmed the pair wed in July 2022.Β 
In August 2024, Us confirmed Lopez filed for divorce from Affleck. The pair finalized their divorce in January 2025.Β  Β 

Β© John Shearer/Invision/AP/Shutterstock

Affleck costarred with Garner in 2001’s Pearl Harbor and 2003’s Daredevil, but their romance wasn’t confirmed until October 2004. The Way Back actor popped the question in April 2005, and they tied the knot in Turks & Caicos in June 2005. The duo welcomed Violet in December 2005, Seraphina in January 2009 and Samuel in February 2012.
After their 10th wedding anniversary, the Live By Night actor and Alias alum announced their separation in June 2015. Their divorce was finalized in October 2018.
In February 2020, the Oscar winner said the β€œbiggest regret” of his life was his divorce from Garner. β€œShame is really toxic. There is no positive byproduct of shame,” he told The New York Times. β€œIt’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing.”

Β© Invision/AP/Shutterstock

Though Affleck kept his romance with the Saturday Night Live producer under wraps until July 2017, multiple sources confirmed to Us that the pair had started hooking up in 2014 during his marriage to Garner. β€œThey were having a full-blown affair,” a source close to Affleck and Garner alleged to Us. β€œThey were sleeping together, sending each other cute texts and meeting up whenever they could.”
Things appeared to be getting serious between Affleck and Shookus, as they wound up moving into an NYC apartment together in November 2017. After they called it quits in August 2018, he briefly dated Shauna Sexton.
Affleck and Shookus reconciled their romance in February 2019, but ended things for good that April.

Β© ROMA / MEGA

Following his romance with Shookus, Affleck was spotted dining with Sexton at Nobu in Malibu in August 2018. Us confirmed that the Argo actor ended his fling with the Playboy model in 2018 after two months. The duo called it quits after they traveled to Big Sky, Montana, together.

Β© MEGA

Affleck and Armas met on set of their upcoming film, Deep Water. The duo sparked romance rumors in March 2020 when they went on a Cuban getaway together. Days later, a fan spotted the Town actor and Knives Out actress β€œmaking out” while waiting in the security line at a Cuban airport.
Us exclusively revealed later that month that the pair were β€œhappy together and officially dating.” In May 2020, a source told Us that Affleck is β€œvery serious” about the Knock Knock star and β€œwants [his] kids to spend time with her so they can get to know her.”
In January 2021, a source confirmed toΒ UsΒ that they had amicably split.
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