Relive Bennifer's 20-Year, Full-Circle Romance

Affleck and Lopez 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 Affleck. "I felt like . . . 'Okay, this is it,'" she said.

Just about six months after "Gigli" began filming, Lopez and Judd 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 Affleck until she'd ended things with Judd. When asked how they first fell in love during a 2003 interview with Dateline's Pat O'Brien, Lopez 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 Affleck and showed off her new six-carat pink diamond ring. When asked about the proposal, J Lo told Sawyer 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 Sawyer about her and Affleck's similar upbringings and revealed how Affleck 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 Affleck in several raunchy scenes, and though it delighted fans, Affleck 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 realized 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, Affleck and Lopez 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 Affleck.

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 realize 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 Affleck 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 Affleck'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 interview, where she revealed the breakup with Affleck 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, Affleck 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 Lopez's May 2021 InStyle cover story, Affleck 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 ARod, reports emerged claiming she was hanging out with Affleck again. A source for People claimed Lopez and Affleck had been spending time together since J Lo's breakup, with Affleck even visiting Lopez 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.

May 2021 was a busy month for Lopez and Affleck. The two continued to spark rumors they were rekindling their romance after Lopez was seen with Affleck near the Big Sky resort in Montana. A source told People at the time, "[Jennifer] spent several days with Ben out of town. They have a strong connection. It's all been quick and intense, but Jennifer is happy." Later in May, the pair were seen in Miami, with Affleck visiting the singer while she was working, according to Page Six.

On May 26, just two days after they were seen in Miami, a source confirmed to Us Weekly that all the speculation was true. "Jen and Ben are both very happy with each [other] and are excited to see where the relationship goes," the source said. "They are full-on dating and very happy together."

In June 2021, Lopez finally confirmed her rekindled relationship with Affleck herself. The "Marry Me" star shared a post on Instagram celebrating her 52nd birthday, looking as amazing as ever in a bikini adorned with gold jewelry. The post contained multiple pictures, the very last one being a photo of her and Affleck kissing. Her caption read, "5 2 … what it do . . ." with a pink heart emoji.

To think there was no such thing as becoming "Instagram official" when this pair first dated back in 2001!

Throughout the summer of 2021, Lopez and Affleck were seen together in public many times, but it wasn't until September 2021 that the two made their red carpet debut since they rekindled their relationship. The pair were pictured PDA-ing, sharing a kiss, and being generally flirty together. Lopez joined Affleck at the Venice International Film Festival in support of his film "The Last Duel" in which he starred with Matt Damon and Adam Driver.

Throughout the remainder of 2021, Bennifer's relationship was going strong, and by February 2022, the singer opened up to People about just how happy she was with her new beau. "I feel so lucky and happy and proud to be with him . . . It's a beautiful love story that we got a second chance," she said.

Lopez also reflected on how their relationship is much different from their initial romance nearly 20 years ago. "We're older now, we're smarter, we have more experience, we're at different places in our lives, we have kids now, and we have to be very conscious of those things. We're so protective because it is such a beautiful time for all of us," she shared.

They say true love is worth waiting for, and for Lopez and Affleck, that couldn't be more true. Almost 20 years after they broke off their engagement in January 2004, the singer announced in her newsletter, "On the JLo," that she and Affleck were once again engaged, calling it "her biggest dream come true."

In the newsletter "How It Went Down," J Lo described how Affleck romantically proposed to her. "Saturday night while at my favorite place on earth (in the bubble bath), my beautiful love got on one knee and proposed," she said via People. "I was taken totally off guard and just looked in his eyes smiling and crying at the same time trying hard to get my head around the fact that after 20 years this was happening all over again, I was quite literally speechless and he said, 'is that a yes?' I said YES of course that's a YES."

Lopez went on to say that the proposal was "nothing fancy at all, but it was the most romantic thing I could've ever imagined" and called her and Affleck "two very lucky people who got a second chance at true love."