Inside Matt Damon And Jennifer Lopez's Relationship

It can be hard for fans of pop culture to tell what any famous person actually thinks about any other famous person. Stars can hang out together, be pictured smiling with one another, and repeatedly work together, giving nothing but glowing interview answers about their relationships, yet rumors can still follow them about secret behind-the-scenes tensions. Things get even more complicated when romance is involved, as is the case with Matt Damon's feelings about his best Bostonian buddy Ben Affleck's on-again, off-again, on-again relationship with music superstar Jennifer Lopez.

Over the years, Damon has publicly offered the couple his support, while privately — at least, according to sources — expressing his concern that they may not be good for each another. Dating expert Julie Spira told Elite Daily that relationships between a friend and their friend's romantic partner can be tricky to navigate, noting, "The goal isn't to create a love triangle, but to show warmth and acceptance of your friend's partner, because, you're not going anywhere as a long-term friend."

So... just how does Damon feel about his long-term friend's long-term romantic partner? It's tough to say, but over the years both Matt Damon and Jennifer Lopez have mentioned each other multiple times in the press. Here's an inside look at their relationship.

Back in the day, Ben Affleck and Jennifer Lopez's first romance was one of the biggest stories in Hollywood. The relationship began when they met on set of the film "Gigli," which wound up becoming a legendarily-awful flop. At the time, though, before the movie was released — before it all went wrong — fans were fascinated by the couple. In the music video for "Jenny From The Block," J.Lo mocked the paparazzi's interest in their love story. The video features scenes of Affleck relaxing with his popstar girlfriend on a yacht, while photographers try to capture their every move. 

The long list of the couple's supporters also included Affleck's best friend Matt Damon, who would later tell Boston Magazine that he fully believed in the relationship. Many people doubted Affleck's intention in, for example, purchasing a massive pink diamond ring for Lopez, wondering if it was all a publicity stunt. Not so, according to Damon. "I felt like, Well, my friend's in love," he said. "That's great, because only serious feelings would keep him around in a situation like that." Shady, much?

"Gigli" wasn't the only movie that Ben Affleck and Jennifer Lopez appeared in together at the height of the Bennifer craze. They also starred together in Kevin Smith's "Jersey Girl," a romcom that saw Affleck playing a single dad trying to woo a graduate student after the death of his wife, played by Lopez. By the time the movie was released, the couple had already broken up, which meant Affleck reassessed the relationship in several interviews to promote the film. For example, he told Black Film that he was better for having withstood so much attention. "I don't have to be on the top of everybody's list career-wise, every movie doesn't have to work," he said. "I'm still fundamentally going to be who I am and that's really what determines my happiness with my friends and my family and the people I love and how I feel about myself."

"Jersey Girl" is also notable because it's one of many films where Affleck also worked with his good buddy Matt Damon. In the wake of "Gigli," it seems likely that Damon agreed to a cameo as a way to boost the movie's profile, thereby supporting Affleck's attempt to repair his and J.Lo's acting reputations. In the film, Damon plays a publicist who interviews Affleck's character for a job, and it feels like a meta moment when Damon's character tells Affleck's, "We bow to you, man. You're like a God around here."

Even though Matt Damon may have believed that Ben Affleck's intentions were pure in pursuing Jennifer Lopez, that doesn't mean he was happy with the way the relationship was covered in the media. In fact, in the same Boston Magazine interview where Damon expressed his support for his friend's overly-romantic gestures, he also decried 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 cross hairs 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. Furthermore, he felt his friend's pain over seeing his talent be overlooked. "It was painful to be his friend," he said, "because it wasn't fair, you know?"

Thanks to Matt Damon's well-documented friendship with Ben Affleck, the "Behind the Candelabra" star has often been asked to comment on Affleck's ongoing relationship with Jennifer Lopez. In 2021, as rumors began to swirl that Bennifer was back together, Damon was asked for his thoughts during an appearance on "TODAY." Declining to confirm the speculation, Damon simply remarked, "There's not enough liquor in the world for you to get me to say something ... I love them both! I hope it's true; that would be awesome."

Lopez appeared on the same show the following year, and at that point, Bennifer was very much a thing again. She took the opportunity to defend Affleck's friend from the morning show hosts, chiding them for the way they had questioned him the year before. "You guys really gave him a hard time," she said (via Entertainment Tonight). "I felt so bad for him. I was like, 'Oh my god.'" This pair of interviews seems to suggest that, no matter what misgivings Damon might have had about the intensity of the effects the first relationship had on his friend, the second time, they all had each other's backs.

When Matt Damon was put on the spot on "TODAY," he expressed support for Ben Affleck getting back together with Jennifer Lopez. That doesn't seem to have been the case behind the scenes, at least according to insiders who spoke to The Daily Mail. Damon apparently warned his "Good Will Hunting" co-star that it was a bad idea to spark up another romance. "Matt tried to warn Ben when he got back together with JLo that this could happen. Matt was there to help Ben get it together after their first split and he felt like this would happen again," the source insisted.

It seems that Affleck had his own misgivings about getting back together with his ex. In "The Greatest Love Story Never Told," a documentary about her efforts to make a film turning J.Lo's relationship history into art, Affleck explained his hesitation (via E! News). "I said, 'Listen, one of the things I don't want is a relationship on social media,'" Affleck recalled telling Lopez. Then he reconsidered. "It's not a fair thing to ask," he decided. "It's sort of like you're gonna marry a boat captain and you go, 'Well, I don't like the water.' We're just two people with kind of different approaches trying to learn to compromise."

By June 2021, Ben Affleck and Jennifer Lopez were definitively back together. "J.Lo and Ben are very much a couple and have been telling friends that they're together," a source told Entertainment Tonight. "When they first reconnected, they had to see if the spark was still there because it had been a while. It was, so now they are both fully in it."

That meant Matt Damon was now free to talk about his friend's new (old) relationship. He expressed his happiness in an interview Extra, telling the outlet, "I'm just so happy for him. He's the best. He deserves every happiness in the world. I'm glad for both of them." Damon reiterated his support on an episode of "The Carlos Watson Show," insisting that he was rooting for the couple to last. "No one's pulling harder than I am. They're both great. I just want for their happiness, and they seem pretty happy right now."

While Ben Affleck and Jennifer Lopez are the couple who typically make headlines, Matt Damon has been in his own relationship for almost two decades. You would think that would lead to plenty of opportunities for double dates, but if those have happened, they haven't typically hit the press. In fact, sources told RadarOnline that Damon and Affleck have tried to set up such dates, but their wives haven't been interested. "It's no secret Matt can't stand Jennifer," a source insisted to the outlet. "He hates what she's done to the free-spirited buddy he used to know. Jennifer feels the need to micromanage Ben's life to an extreme degree, and now Ben's so badgered and browbeaten he doesn't have the strength to stand up for himself."

There are two major outliers, though. Up first, the 2024 Golden Globes, which saw Damon and Affleck sitting together with their wives during the ceremony. A few months later, in April 2024, Lopez was spotted getting lunch with the "We Bought A Zoo" star and his wife, Luciana Barroso. Affleck, on the other hand, doesn't seem to have been present, according to People. If Lopez and Damon sometimes hang out without Affleck, that would certainly lend credence to Damon's insistence that he loves both halves of the couple separately. In other words, from the outside looking in, it's tough to tell how anyone involved feels about each other.

In the first half of 2024, media speculation suggested Ben Affleck and Jennifer Lopez were headed for a second split. As the two were filmed getting into arguments, spending time apart, and facing professional setbacks like the cancellation of Lopez's tour, divorce rumors seemed to follow the couple everywhere they went.

Reportedly, Affleck has been leaning on Matt Damon for support. Damon, for his part, seems to be frustrated that his friend once again put his own career to the side to help the "Waiting For Tonight" hitmaker. "Ben spent so much time focusing on J.Lo's projects just like he did the first time around," a source told The Daily Mail. "[Matt] told Ben, 'What has she ever done for your career?'"

Sources also spoke with InTouch about the specific ways Damon is showing up for Affleck while Lopez may or may not be preparing to go her own way. "Matt's No. 1 priority right now is keeping Ben out of trouble. The last thing anyone wants is for Ben to turn to alcohol again," the source said. "Matt has straight out told him that relapse is not an option." Instead, Damon has apparently suggested that Affleck focus on spending time with the other Jennifer — Garner, that is, Affleck's ex-wife and the mother of his kids. They'll also be working on a new film together. "Anything," the source said, "to keep him from having idle time on his hands."