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 his New York Times profile from February 2020, 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.”
The Reindeer Games actor’s longest relationship began in 2004 with Jennifer Garner, whom he began dating after his on-and-off romance with Gwyneth Paltrow and his broken engagement to Lopez. 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 actresses have 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 co-parenting” 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.
Scroll down to see Affleck’s greatest loves and flings throughout the years.