Ben Affleck is no stranger to a high-profile romance — 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-fiancée Jennifer Lopez after her 2020 Academy Awards snub for her work in Hustlers.
“She 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. “How awesome is it that she had her biggest hit movie at 50? That’s f–king baller.”
Luckily, the Argo producer’s sweet words did him some good. In May 2021, Us Weekly confirmed the pair were back together after splitting more than a decade earlier.
“The old flame is absolutely rekindled. They picked up where they left off in terms of affection for each other,” a source shared at the time. In April 2022, Lopez confirmed that the couple were officially engaged for the second time.
But let’s rewind! The Reindeer Games actor’s longest relationship began in 2004 with Jennifer Garner, whom he began dating after breaking his engagement to the “I’m Real” singer and pursuing an on-and-off romance with Gwyneth Paltrow. The exes — who share daughters Violet and Seraphina and son Samuel — were married from June 2005 until they announced their separation in June 2015.
Despite their split, the 13 Going on 30 actress has become someone Affleck can turn to in his time of need, including during his recovery journey. “Jen has always been the person who can get through to him,” an insider told Us in 2017. “She keeps Ben in line as much as she can.”
In August 2019, a source told Us exclusively that Affleck and Garner were doing “amazingly well at coparenting” their children together.
In addition to his romances with Garner, Lopez and Paltrow, he has also been rumored to have dated quite a few other costars. Affleck sparked dating speculation with Salma Hayek in 1999 and Jaime King in 2001, to name a few. But after his broken marriage to Garner, he says he’s holding out for the real thing.
“I would love to have a relationship that was deeply meaningful,” Affleck told Good Morning America’s Diane Sawyer in February 2020. “And one to which I could be deeply committed.”
Us exclusively revealed in March 2020 that Affleck was dating his Deep Water costar Ana De Armas. “Ben is very supportive of Ana and tells her how amazing she is,” an insider told Us at the time “Ana’s friends are constantly telling her how lucky she is to have Ben and think he is so charming, cool and fun. They’re so happy for her.”
However, the duo called it quits in January 2021 — months before he found his way back to Lopez.
“Friends say they can see them staying together forever this time around,” a source shared of the Gigli costars in June 2021. “They are soulmates and always have been.”
Scroll down to see Affleck’s greatest loves and flings throughout the years.
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. Newscom/MEGA
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. Alex Berliner/BEI/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 “On the Floor” singer, who earned the power couple name of “Bennifer” 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 “always 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. Richard Young/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 “biggest regret” of his life was his divorce from Garner. “Shame is really toxic. There is no positive byproduct of shame,” he told The New York Times. “It’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing.” John Shearer/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. “They were having a full-blown affair,” a source close to Affleck and Garner alleged to Us. “They 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. Invision/AP/Shutterstock
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. ROMA / 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 “making out” while waiting in the security line at a Cuban airport. Us exclusively revealed later that month that the pair were “happy together and officially dating.” In May 2020, a source told Us that Affleck is “very serious” about the Knock Knock star and “wants [his] kids to spend time with her so they can get to know her.” In January 2021, a source confirmed to Us that they had amicably split. MEGA
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