Jennifer Lopez and Ben Affleck's Relationship Timeline Represents an Iconic 2000s Moment

Ben and Jennifer first crossed paths in late 2001 on the set of 2003’s Gigli. The movie may have been a box office bomb, but sparks were definitely flying between the two stars off set. At the time, J Lo was still married to her second husband, dancer Cris Judd, but as she later recalled during a 2016 interview with People, she knew she had something special with Ben. “I felt like . . . ‘Okay, this is it,'” she said.

Just about six months after Gigli began filming, Jennifer and Cris decided to separate, and in July 2002, J Lo officially filed for divorce, citing irreconcilable differences. Not long after, Bennifer was born, though Jennifer insisted nothing happened between her and Ben until she’d ended things with Cris. When asked how they first fell in love during a 2003 interview with Dateline‘s Pat O’Brien, Jennifer said, “You can’t pinpoint it. We became friends first. That is the honest to God truth.”

During a November 2002 interview with Diane Sawyer, Jennifer announced her engagement to Ben and showed off her new 6-carat pink diamond ring. When asked about the proposal, J Lo told Diane it was “traditional, but also in a very spectacular way, as of course Ben would do it . . . It was very, very beautiful.” She also gushed to Diane about her and Ben’s similar upbringings and revealed how Ben won over her mother.

Right around the same time, the music video for “Jenny from the Block” made its debut on TRL. The video prominently featured Ben in several raunchy scenes, and though it delighted fans, Ben later admitted he regretted the move. “If I have a regret, it was doing the [‘Jenny from the Block’] music video,” he told Daily Record in 2008. “But that happened years ago. I’ve moved on.”

Just four days before they planned to say “I do” in Santa Barbara, Bennifer decided to delay the big day, shocking fans. “Due to the excessive media attention surrounding our wedding, we have decided to postpone the date,” the couple confirmed in a statement. “When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realised that something was awry. We began to feel that the spirit of what should have been the happiest day of our lives could be compromised. We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends.”

In January 2004, four months after postponing their wedding, Ben and Jennifer announced they’d called off their engagement for good. “I am confirming the report that Jennifer Lopez has ended her engagement to Ben Affleck,” her rep said in a statement at the time. “At this difficult time, we ask that you respect her privacy.” Though a reason wasn’t provided, it was widely reported that the constant media attention became too much for Ben.

A few weeks after the initial breakup reports emerged, a source close to the couple told People the relationship had been deteriorating for months. “It was hard to merge their two lifestyles,” the insider claimed. “When you love someone, the media circus does not get in the way. You say, ‘Okay, we’ll figure it out. Let’s do it.’ Jennifer didn’t realise it at that moment, but when [Ben] called [the wedding] off, the relationship was over. He got out of the trap and he wasn’t going to get back in. He was looking for a graceful way to let it die.”

The breakup remained a mystery for years until Ben opened up about the split during a 2008 appearance on the British TV show Live. According to him, the constant media scrutiny did put a strain on the relationship, as fans suspected. “I think Jen and I made a mistake in that we fell in love, we were excited and maybe too accessible,” he explained. “I don’t think either of us anticipated the degree to which it would take on a world of its own.”

Almost seven-and-a-half years after Ben’s interview, J Lo told her own side of the story during a 2016 interview with People. She expressed a similar sentiment, saying pressure from the public made the romance unsustainable. “We didn’t try to have a public relationship,” she said. “We just happened to be together at the birth of the tabloids, and it was like ‘Oh my God.’ It was just a lot of pressure . . . I think different time different thing, who knows what could’ve happened, but there was a genuine love there.”

She reflected on the demise of their relationship again during her December 2017 Vanity Fair cover story interview, where she revealed the breakup with Ben had been devastating. ” . . . my relationship [with Ben] self-destructed in front of the entire world,” she said. “It was a two-year thing for me until I picked myself up again.”

Many fans were bummed when J Lo didn’t receive an Oscar nod for her work in 2019’s Hustlers, and apparently, Ben was equally disappointed. “She should have been nominated,” he told New York Times reporter Brooks Barnes soon after the nominations were released. “She’s the real thing. I keep in touch periodically with her and have a lot of respect for her. How awesome is it that she had her biggest hit movie at 50? That’s f*cking baller.”

Just about a year later, when he was interviewed for Jennifer’s May 2021 InStyle cover story, Ben praised his ex once again while reflecting on their time working together on Gigli and on their 2004 film Jersey Girl. “She remains, to this day, the hardest-working person I’ve come across in this business,” he gushed. “She has great talent, but she has also worked very hard for her success, and I’m so happy for her that she seems, at long last, to be getting the credit she deserves.”

In April 2021, not long after J Lo announced her split from A-Rod, reports emerged claiming she was hanging out with Ben once again. A source for People claimed Jennifer and Ben have been spending time together since J Lo’s breakup, with Ben even visiting Jennifer at her Los Angeles home on April 30. “They are friends. They have always been friends and they have seen each other through the years,” another source told the outlet. Fans will just have to wait and see whether these two are rekindling more than just a friendship.