Matt Damon and Jennifer Lopez: Inside Their Relationship

Even though Matt Damon believed that Ben Affleck’s intentions were genuine in pursuing Jennifer Lopez, he wasn’t pleased with how the media covered their relationship. In the same interview with Boston Magazine where Damon expressed support for his friend’s overly-romantic gestures, he criticized the intense speculation that surrounded the couple at that time. “I think it’s funny when people accuse him of wanting that attention because every actor knows that if you end up in the crosshairs of those kinds of publications, your movies aren’t going to do any business,” Damon said. “Why am I going to pay $10 to see that guy in a movie when on Monday, here he is getting a Starbucks, Tuesday, here he is in a bookstore.”

More than a decade after Affleck and Lopez went their separate ways, Damon assessed the fallout on his friend’s career in a 2015 interview with The Hollywood Reporter. This time, years removed from the situation, Damon didn’t hold back. “It was like he was being cast in a role, that he was a talentless kind of meathead, with his whole relationship with Jennifer Lopez. He just got cast as this person that he wasn’t,” Damon reflected. He felt deeply for his friend’s plight of having his talent overlooked. “It was painful to be his friend,” he said, “because it wasn’t fair, you know?”