The Ultimate Sign J.Lo And Ben Affleck Should've Never Given Their Romance A Second Shot

Despite its many fairytale-like qualities, Ben Affleck and Jennifer Lopez's reunion had some glaring red flags from the very beginning that went largely unnoticed. Their paths first crossed in 2002 when the actors joined forces for "Gigli." Back then, the "Jenny From The Block" hitmaker was about a year into her marriage to Cris Judd. But they called things off in July, and Lopez made her romance with Affleck official soon afterward. The celebrity couple had a whirlwind courtship, with the "Gone Girl" star popping the question later in 2002. However, Affleck and Lopez ended up canceling their 2003 wedding and the decision understandably hurt their relationship. The A-listers then went their separate ways in 2004. 

Their love story was far from over, though, as Affleck and Lopez got back together in 2021 and tied the knot the following year. Then, in 2024, we started seeing several signs that Affleck and Lopez were headed for a second split. Amidst all the drama, we also learned that Affleck reportedly drove a wedge between J.Lo and her longtime BFF Leah Remini thanks to a Page Six article. A source revealed that Remini was unsure about her friend's rekindled romance and strongly urged Lopez to reflect on how they broke up the first time "because he is selfish and is not fully committed as a partner." Lopez didn't take kindly to her advice, stopped speaking to Remini, and didn't even send her an invitation to their wedding. But Remini wasn't the only one in Lopez's inner circle who didn't like Affleck.

In August 2024, an insider informed Page Six that Jennifer Lopez's manager, Benny Medina, was never particularly keen on her relationship with Ben Affleck — even back in 2002. The source claimed that Medina's dislike for the "Justice League" star was one of the many reasons why Lopez briefly stopped employing him in 2003. "The two of them can't stand each other. They don't get along and there's still bad blood," the confidant disclosed of Medina and Affleck's dynamic after the "On The Floor" songstress rekindled things with him. However, Medina wisely held his tongue this time around: "His attitude was, 'I'm gonna say nothing.' [There] was no, 'Good for you,' but also, [he] wasn't negative."

J.Lo's longtime manager chose not to voice his true feelings about Affleck because he knew that she had made up her mind about tying the knot with him. Ultimately, though, another source confirmed that the actor wasn't popular with most of Lopez's other loved ones either, confessing, "No one, except [Lopez's] mother, likes Ben Affleck. He's a triple-A a*****." On the other hand, the "Argo" director's inner circle wasn't entirely sold on Lopez. Also in 2024, a source divulged to the Daily Mail that one of his closest friends, fellow actor Matt Damon, was there to pick up the pieces after their initial breakup and cautioned Affleck that he may have to face a similar outcome after getting back together with her.

With rumors about Ben Affleck and Jennifer Lopez's marital problems swirling, a source revealed to the Daily Mail that Matt Damon had reassured his longtime friend and collaborator that he would have his back whether Affleck chose to stay in the marriage or get a divorce. Regardless of what he decided, the "Good Will Hunting" star encouraged Affleck to consider something crucial. "Ben spent so much time focusing on J.Lo's projects just like he did the first time around," they pointed out. So, "He told Ben, 'What has she ever done for your career?'" 

Likewise, another insider previously told OK! magazine that the "The Martian" actor wasn't entirely on board with the idea of Affleck and Lopez reconciling from the get-go, and Damon's concerns about their relationship only worsened as time went by. "He's tried to be publicly supportive for Ben's sake, but the fact is he hates the way J.Lo treats his buddy and can no longer hold his tongue," the source explained. They further asserted that the "Oppenheimer" star took issue with how "emasculate[d]" Affleck apparently felt in their high-profile relationship.

Damon tried making his buddy aware of the many red flags he'd spotted over the course of their relationship, but the two-time Oscar winner didn't welcome the intrusion and got quite defensive. Fortunately, Affleck and Damon's long-standing friendship wasn't affected by their disagreements. According to an Entertainment Tonight insider, Damon was incredibly supportive as his BFF dealt with the rumored end of his marriage.