The Rise And Fall Of Ben Affleck And Jennifer Lopez's Love Story

The tale of A-list actor Ben Affleck and multi-talented singer Jennifer Lopez's love story has spanned decades, films, hundreds of salacious tabloid stories, and even two unsuccessful engagements. The two movie stars were one of the hottest couples to watch in the early 2000s, ultimately earning their nickname "Bennifer" and dazzling their millions of adoring fans with their red-carpet appearances and striking star power. They ultimately split in 2004, however, shocking fans everywhere when they decided they weren't meant to be.

The couple reunited nearly two decades later, delighting fans when they rekindled their romance after splitting with their previous partners. Another engagement, a surprise Las Vegas wedding, and a shared Los Angeles mansion weren't enough to keep this couple together, however, and Bennifer called it quits yet again in 2024 — with JLo filing for divorce.

Despite many fans rooting for them to ride off into the Los Angeles sunset together, this pair can't seem to find their footing in the dog-eat-dog-world of Hollywood. Many have speculated that the "JLo Effect" – which refers to her ability to influence pop culture in droves and only get better with age — may have been too much for Affleck's low-profile lifestyle. While we wait for a Bennifer-inspired breakup album, here's a look at the rise and fall of Ben Affleck and Jennifer Lopez's love story.

Jennifer Lopez immediately fell hard for Ben Affleck, admitting that something inside her had shifted upon meeting him. The two first crossed paths in 2002 while filming the movie "Gigli," when the "Let's Get Loud" singer was still married to her then-husband Cris Judd. But her instant chemistry with the actor was obvious both on and off the screen, and it wasn't long before she and Judd called off their marriage and she and Affleck went public with their romance.

"I felt like ... 'Okay, this is it,'" the singer recalled to People in 2016. The dawn of the frenzied paparazzi and tabloid era meant that the couple was subject to incessant media attention, and soon Bennifer was born. From star-studded red-carpet appearances to Affleck's iconic appearance in her "Jenny from the Block" music video, the public couldn't get enough of their romance.

It wasn't long after Bennifer was born in the summer of 2002 that Ben Affleck and Jennifer Lopez decided to get hitched. In a whirlwind move, the couple got engaged just months after their romance first reached the tabloids. The singer revealed the news in an interview with Diane Sawyer in November of that year, admitting that the "Air" star popped the question with a pink-solitaire diamond that was reportedly worth a whopping $2.5 million at the time.

While Lopez initially told Sawyer she thought Affleck was a typical Hollywood bad boy, or "skirt chaser" as she referred to him, he ultimately proved her wrong. She described him as, "Brilliantly smart ... Loving. Charming. Affectionate," adding, "And I just admire him in every way."

As for Affleck, he admitted that his strong friendship with Lopez set the tone for their incredible bond. "Because she was married, there was no thought of a romantic relationship, so that created the opportunity to get to know each other without any of the falseness that goes with courtship because you're trying to make a good impression," he told Vanity Fair in 2003. "I didn't try to change anything about myself, and she didn't either."

The media circus that surrounded every move Jennifer Lopez and Ben Affleck made together seemed to cause their first split. While the couple had planned to get married in the fall of 2003, they decided to postpone the date due to the tabloid attention at the time. "When we found ourselves seriously contemplating hiring three separate 'decoy brides' at three different locations, we realized that something was awry," the couple said in a statement to People at the time. "We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends."

Their relationship seemed to only deteriorate after the fact, as the couple broke up not long after in January of 2004. In a 2022 interview with Apple Music (via Elle), the "On the Floor" singer blamed their split on a lack of maturity, admitting, "We weren't ready to deal with and look at each other and go, 'What we have is real, we need to buckle down, we need to do some work.' We just weren't there yet."

While JLo put on a brave face for the rest of the world, inside she was suffering. She recalled in another interview with Zane Lowe for Apple Music that the breakup was one of the hardest things she ever went through, saying, "It was the biggest heartbreak of my life. And I honestly felt like I was gonna die. And it sent me on a spiral for the next 18 years where I  ...  couldn't get it right."

After their fairytale wedding wasn't meant to be, Jennifer Lopez and Ben Affleck found love with other people. Unfortunately for Lopez, Affleck's love interest shared the same name as his ex-bride-to-be. The actor started dating his former co-star, Jennifer Garner, in 2004, and the two tied the knot in 2005. Garner and Affleck went on to have three children together, their daughters, Violet and Seraphina, and their son, Samuel.

As for the "Shotgun Wedding" star, she married her long-time music collaborator Marc Anthony in 2004, in a much more low-profile affair — held at her home in Los Angeles — than what was set to be her and Affleck's nuptials. Lopez and Anthony had fraternal twins Emme and Max in 2008, and she became a stepmother to his four other kids from previous relationships.

Both Jennifer Lopez's and Ben Affleck's subsequent relationships didn't work out, giving hope to all the Bennifer stans. Affleck and Jennifer Garner called it quits in 2015 when they announced their plans to divorce, but continued to remain on amicable terms and co-parent their three children together. Eventually, three years after the announcement of their split, the former spouses finalized their divorce in 2018. Affleck speaks highly of his former wife, however, telling People in 2020, "When you have children with somebody you're connected to them forever. And I'm very lucky she is the mother of my children. I'm very grateful and respectful of her."

Marc Anthony and Lopez's breakup was made public in 2011, with Anthony filing for divorce a year later and listing "irreconcilable differences" as the motive for the split. Their divorce was finalized in 2014, and the two remained co-collaborators in the music industry and continued to be on good terms with each other in the years that followed (even sharing a kiss on stage together two years later). "If you want to get along with a woman, just get divorced," Anthony joked to Extra TV about their post-divorce relationship.

Despite Jennifer Lopez and Ben Affleck's relationship crumbling under media pressure in the early 2000s, the two shared a mutual respect for one another that seemed to never burn out. The Boston-bred actor praised Lopez's work in the 2019 film, "Hustlers," telling New York Times journalist Brooks Barnes he was rooting for her to be in the running for an Oscar for her lead role in the movie. "She should have been nominated. She's the real thing," Affleck enthused to the journalist (via X, formerly known as Twitter). "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***ing baller."

We can't forget that JLo also notoriously playfully slapped her former beau's arm at the 2015 Academy Awards, which seemed to cause more headlines than many of that year's winners. Tabloids were quick to report on the incident, which occurred after the actor whispered something mysteriously into Lopez's ear during a commercial break. They say silence speaks a thousand words...

Alex Rodriguez and Jennifer Lopez first met in 1999 when she signed an autograph for the former professional baseball player, but it wouldn't be until many years later that they became an item. After running into each other a few times over the years, Rodriguez finally asked Lopez on a date in 2017. A few months later, the couple made it Instagram official, and it seemed like a perfect match. "We are very much twins," Rodriguez admitted in their joint cover story for Vanity Fair in 2017. "We're both Leos, we're both from New York, we're both Latino and about 20 other things."

JLo and A-Rod got engaged in 2019 during a trip to the Bahamas, but the two weren't in any rush to get married or make plans for the big day. Nearly two years after Rodriguez popped the question, however, reports surfaced of tensions between the two, and their breakup followed in April of 2021. "We have realized we are better as friends and look forward to remaining so," their joint statement to Today read.

After splitting with Jennifer Garner in 2015, Ben Affleck dated several different women in the years that followed. He started dating producer Lindsay Shookus in 2017, and the pair quickly moved in together just a few months later. Shookus and Affleck endured their ups and downs, splitting in August of 2018, briefly reconciling, and later breaking up for good in the spring of 2019.

He made headlines for his bachelor-like ways when he was seen out on the town with Playboy model Shauna Sexton in 2018 while he and Shookus had been going through a breakup at the time. While the two were seen out and about for a few months, their relationship was never considered serious. He also had a brief relationship with Katie Cherry, whom he met in 2019 on the A-lister dating app Raya. The pair dated casually for about three months before calling it quits.

Affleck moved on to his "Deep Water" co-star, Ana de Armas, in the spring of 2020, with whom he spent the majority of that year's COVID-19 pandemic. The two were spotted vacationing together in Cuba (Armas' home country) and doing errands together alongside Affleck's kids throughout 2020, but eventually their flame fizzled out in January of 2021. "She broke it off," a source confirmed to People at the time. "Their relationship was complicated. Ana doesn't want to be Los Angeles-based, and Ben obviously has to since his kids live in Los Angeles."

To the amazement of millions of fans across the world, Bennifer came back in full force in July of 2021. Amid a series of sizzling hot bikini photos that JLo posted on Instagram in celebration of her 52nd birthday, she shared a steamy photo of her kissing her former flame Ben Affleck. "5 2 ... what it do ..." she captioned the post. 

The pair walked their first red carpet together in nearly two decades a few months later for the premiere of Affleck's film, "The Last Duel." They continued to appear together at Hollywood events, including the Met Gala, and it seemed like the two had hit a home run their second time around. "I feel so lucky and happy and proud to be with him," Lopez told People in 2022. "It's a beautiful love story that we got a second chance."

While their first chance at romance took a turn due to the insane media circus that surrounded them, JLo felt that the two had a different approach to their rekindled love affair. "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," she explained to the publication. "We're so protective because it is such a beautiful time for all of us."

Jennifer Lopez got engaged for the sixth time in 2022 — but who's counting? The star announced the news in her OnTheJLo newsletter that Ben Affleck had asked her to marry him with a giant diamond in April of that year. In the video, Lopez shows off the sparkler on her ring finger while listening along to her song, "Dear Ben."

She detailed how her man popped the question, saying (via Extra TV), "Ben came in and he got down on one knee and he said some things that I'll never forget ... and he pulled out a ring and he said, 'Will you marry me.'" The singer, clearly emotional over her exciting new chapter, called it "the most perfect moment." Lopez revealed that Affleck got her a green diamond, which she revealed was her favorite color and one that brought her good luck.

Jennifer Lopez and Ben Affleck tied the knot in a surprise Las Vegas wedding just a few months after the "Good Will Hunting" star popped the question. The singer detailed the special day to People, revealing that their children acted as witnesses during the nuptials. "It's a beautiful outcome that this has happened in this way at this time in our lives where we can really appreciate and celebrate each other and respect each other," Lopez gushed. She also reflected on how their unique love story came full circle, saying, "We always did, but we have even more of an appreciation because we know that life can take you in different directions."

About a month later, the couple celebrated their marriage with a separate ceremony in Georgia amongst their closest friends and family members. The event took place on Affleck's giant nearly 90-acre property outside of Savannah, with Lopez dazzling down the aisle in a Ralph Lauren gown. After they said "I do" for the second time, the pair jetted off to Italy to enjoy their honeymoon around Lake Como and Milan. A source revealed that the couple remained low-key during their get-away, keeping in tune with Affleck's more private lifestyle. "They just queued up for ice cream like everyone else, and wandered into shops," the insider told People. "They acted normally, even if they had bodyguards with them."

What says commitment like permanent ink? That seemed to be Ben Affleck and Jennifer Lopez's thoughts exactly when they celebrated their love and recent move-in together with two matching tattoos. The couple started living together in January of 2023, with Lopez revealing the news in an interview with Today, "We moved in together, the kids moved in together, so it's been like a really kind of emotional transition." She went on to add, "But at the same time, all your dreams coming true, it's just been a phenomenal year."

Not long after, the singer revealed she and her beau got matching tattoos declaring their love for one another. "Commitment ... Happy Valentine's Day my love," she wrote in an Instagram post that featured a series of photos of the couple, including shots of their similar ink designs. Lopez's tattoo was placed on her ribcage, and featured an infinity design with an arrow through it, with what appeared to be her and Affleck's names written. The "Argo" star's tattoo design featured two arrows crossing each other with the letters "J" and "B."

In May of 2023, the pair purchased an over $60 million home together after years of looking for their ideal digs. The Beverly Hills mansion came with a 12-car garage, a pool and hot tub, basketball and pickleball courts, 12 rooms, 24 bathrooms, and incredible mountain views.

Trouble appeared to start brewing in Ben Affleck and Jennifer Lopez's relationship around May 2024 when the couple hadn't been photographed side by side in over a month. The couple was seen together at Affleck's daughter Violet's graduation ceremony later that month, but it wasn't long before tensions came to a head. By late June, the actor was seen moving his stuff out of their shared home and a source revealed to People that he was staying at a rental nearby. 

In August of that year, an insider told the publication that the couple was going their separate ways. "Jennifer is trying to find a new home to start fresh," the source revealed to People. Later that month, JLo filed for divorce from Affleck, on the same day they had tied the knot in Georgia two years ago. The singer named "irreconcilable differences" as the reason for the split and filed without a lawyer.

Reports suggested that there seemed to be disagreements about how much should be made public about their love affair. The singer revealed intimate letters that she kept through the decades that Affleck had written to her in the early 2000s in her documentary, "The Greatest Love Story Never Told," but Affleck wasn't exactly 10 toes behind her. "I don't think he's very comfortable with me doing all of this," she revealed in the film (per New York Post). "But he loves me, he knows I'm an artist and he's going to support me in every way he can."

A source told People that Affleck may have had a darker side to him that contributed to the downfall of their marriage. "You could see the erratic behavior, the giant mood swings," the source explained of the actor. "Being incredibly happy and warm — the best light that emanated from him" to showing "the deepest, darkest behavior."