A Comprehensive Timeline of Bennifer, Perhaps the Greatest Love Story of Our Time

20 minute read

There are few pairs that have embodied the frenzied obsession with celebrity duos quite like Ben Affleck and Jennifer Lopez, one of the super couples of the early-aughts tabloid era, whose rekindled romance after 20-plus years has delighted hopeless romantics and pop-culture fanatics alike. Over the course of two decades, Affleck and Lopez’s relationship has touched on nearly every storyline of a Hollywood romance, from their flashy early courtship and messy breakup to their fairy-tale reconciliation and eventual marriage. The public fascination with their relationship has inspired everything from a South Park episode to the creation of a joint moniker (hello, Bennifer!), making the duo a cultural touchstone in the process.

Which might explain why Lopez (and a seemingly begrudging but loving Affleck) decided to tell the story of their relationship in a recent documentary, The Greatest Love Story Never Told. The film, streaming on Amazon Prime and drawing its name from a description of their romance in one of the real-life love letters Affleck wrote Lopez, is ostensibly about the making of her bombastic musical movie This Is Me…Now and its accompanying album, released in February. But really, it sets out to make the case that Bennifer might be one of the greatest love stories of our time.

Read more: Why Jennifer Lopez Remains the Patron Saint of Romantic Comedies

Like This Is Me…Now, The Greatest Love Story Never Told can be bewildering in its ambition and chaotic in its storytelling, but there was one scene that shocked me into seriously examining the epic romance between Affleck and Lopez. Early on in the documentary, Lopez shares with her team the Christmas gift that Affleck gave to her in 2021, an extensive scrapbook chronicling every picture, email and letter the two have shared since they first met in 2001. The moment itself, though casual, is breathtaking when you realize that Affleck, a two-time Oscar winner so known for his seemingly downtrodden stoicism that he inspired a meme, retrieved every piece of correspondence with a woman he fell in love with over 20 years ago, then presented it all to her when they reunited two decades later. Perhaps even more astounding is that Lopez uses this as the jumping-off point for her new album and film, basically offering the most private and vulnerable part of a highly public relationship for her art.

The couple met in 2001 on the set of the objectively bad film Gigli, where their workplace romance grew into one of the most emblematic celebrity couplings of the era—Lopez, a pop star and rom-com golden girl from the Bronx and Affleck, the Oscar-winning bad boy from Boston. Their relationship blossomed under the watchful eye of the tabloids, and in spite of it, solidifying them as true A-listers whose personal lives were as compelling as their work on-screen. While cynics may have pointed to the high-profile pairing as a ploy to boost their celebrity, Lopez and Affleck’s displays of affection came off as pure romance, authentic if outsized. How else to explain Affleck taking out full-page ads in trade rags to congratulate Lopez after she won an award, or Lopez penning a love song on her 2002 album This Is Me…Then, titled, “Dear Ben,” and dedicating the entire album to him? Or what about Affleck proposing to Lopez, after just over a year of dating, with a 6.1 carat pink diamond from Harry Winston? Their whirlwind romance was fantastical, heady, even giddy, the equivalent of watching a rom-com in real time.

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Lopez famously poked fun of the relentless media scrutiny around Bennifer in her 2002 music video for “Jenny from the Block,” in which Affleck cameoed as himself, notoriously kissing her bikini-clad posterior on a yacht, as the paparazzi swarmed. But in real life, it led to the couple postponing their wedding in September 2003, just three days before their planned nuptials. “Due to the excessive media attention surrounding our wedding, we have decided to postpone the date," they said in a statement. "When we found ourselves seriously contemplating hiring three separate 'decoy brides' at three different locations, we realized that something was awry.”

The pair broke up in early 2004, before swiftly jumping into new relationships—Lopez married singer Marc Anthony in June 2004, while Affleck wed actor Jennifer Garner in June 2005. Over the next two decades, they both welcomed children, went through divorces, and weathered undue media scrutiny. This came for things as insignificant as a back tattoo and smoking while looking disinterested, and as sobering as a rumored cheating scandal (Affleck's divorce from Garner came on the heels of an alleged affair with their one-time nanny, Christine Ouzonian; Affleck denied any romantic or sexual relationship with her) and the breaking of an engagement (Lopez called off her engagement to baseball star Alex Rodriguez amid reports of his infidelity). They lived, arguably, an entire lifetime without each other before they gloriously, miraculously, reentered each other’s lives in mid-2021, in the ultimate pandemic reconnection with an ex.

Read more: A Guide to All the Cameos in Jennifer Lopez’s Star-Studded This Is Me…Now: A Love Story

Once again, their romance captivated like a real-life rom-com, providing endless thrills to those watching while socially distancing at home as Lopez went Instagram official with Affleck by posting photos of the couple on a yacht for her birthday that summer, seemingly recreating their scenes from “Jenny from the Block.” Like its OG counterpart, Bennifer 2.0 has had no shortage of delights, from corny couples Dunkin’ Donuts commercials and gushing interviews to its very whirlwind nature—the pair were engaged by April 2022 before getting married not just once, but twice. While their rekindled romance has given us many things, This Is Me…Now and The Greatest Love Story Never Told among them, it’s been a reminder that as long as Bennifer is in this world, romance is alive and well.

Here, a comprehensive look back at Jennifer Lopez and Ben Affleck’s relationship history.

December 2001: Affleck and Lopez meet on the set of Gigli

Actors Ben Affleck and Jennifer Lopez on the set of "Gigli"
LOS ANGELES, JANUARY 9: Actress Jennifer Lopez and actor/fiancee Ben Affleck film a scene on the set of the upcoming film 'Gigli' on January 9, 2003 in Los Angeles, California. (Photo by Mel Bouzad/Getty Images)Getty Images—2003 Getty Images

While Lopez and Affleck said they had been at parties together in the past, they didn’t formally meet until they began working together on the set of the romantic comedy Gigli. Affleck played the titular role of Larry Gigli, an L.A. mobster who hires Ricki, a hit-woman, played by Lopez.

In a 2003 interview with Vanity Fair, Affleck says that while he and Lopez connected quickly on the set of Gigli, it was entirely platonic because she was married at the time. In the fall of 2001, Lopez married Chris Judd, one of the back-up dancers in her "Love Don't Cost a Thing" music video.

“When I met her, we became really, really, really good friends,” he said. “But at first, 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."

March 2002: Affleck places full-page ads in trade publications in support of Lopez

After Lopez was named ShoWest's Female Star of the Year, Affleck took out full-page ads in the Hollywood Reporter and Variety in support of her. While Affleck claimed that his ads for Lopez were written to counteract narratives that she was a diva or difficult to work with, his glowing message to her piqued interest in their relationship.

“You have shown kindness, dedication, diligence, humility, graciousness of spirit, beauty in courage, great empathy, astonishing talent, real poise and true grace,” he wrote. “It has been nothing but an honor and a pleasure to work with you. I only wish I were lucky enough to be in all your movies. With love, respect and gratitude, Ben Affleck.''

July 2002: Lopez divorces husband Cris Judd

74th Annual Academy Awards - Governors Ball
Jennifer Lopez and husband Chris Judd at the Governors Ball following the 74th Annual Academy Awards at the kodak Theater in Hollwood, Ca., 3/24/02. Photo by Frank Micelotta/ImageDirect.Getty Images

Lopez divorced Judd after nine months of marriage, citing irreconcilable differences. Judd was her second husband (she was previously married to actor Ojani Noa).

While Affleck emphasized in his Vanity Fair interview that he didn’t think about Lopez romantically when they met, he said things changed after she told him that she was splitting from her husband. 

"It changed when she told me she was getting separated," Affleck said. "At that point, it became a possibility; doors were opened."

November 2002: Affleck and Lopez star in her music video for “Jenny from the Block”

For her music video for “Jenny from the Block,” a single off her then upcoming album, This Is Me…Then, Lopez and Affleck appeared as versions of themselves, trying to escape the paparazzi. The video used imaginary surveillance footage, as well as shots of the couple on a yacht, by the pool, and eating outside at a restaurant to seemingly critique the relentless media scrutiny the pair experienced.

November 2002: Affleck and Lopez begin filming Jersey Girl

Jennifer Lopez and Ben Affleck Filming "Jersey Girl" in Central Park
Ben Affleck and Jennifer Lopez during Jennifer Lopez and Ben Affleck Filming "Jersey Girl" in Central Park at Central Park, Manhattan in New York City, New York, United States. (Photo by Tom Kingston/WireImage)WireImage

That same month, Affleck and Lopez began filming their second film together, Jersey Girl, in which they appear as a husband and wife.

November 2002: Affleck and Lopez confirm their engagement

In a Prime Time interview with Diane Sawyer, Lopez confirmed their engagement, which many had speculated about after she was spotted wearing a 6 carat pink diamond Harry Winston ring on her ring finger. According to Lopez, the proposal took place during a private moment in Affleck’s hometown of Boston.

"It's just a blanket, a quilt of rose petals, all over the whole entire house," Lopez said, noting that the engagement also included Affleck reading a handwritten letter listing the reasons why he loved her. "So many candles, and vases, bouquets. And my song 'Glad' was playing...I walk in and I was just overwhelmed. I wasn't expecting it, and I was just like 'Oh my God.'"

Nov. 26, 2002: Lopez releases This Is Me…Then

Lopez’s third studio album, This Is Me…Then, was largely inspired by her relationship with Affleck, which was blossoming as she was writing and recording the project. The influence of their romance on her work may be most overtly seen in her song “Dear Ben,” a musical love letter to Affleck, which includes the lyrics: “I write this song to let you know/ That you will always be to me/ My lust, my love, my man/ my child, my friend, and my king.” Lopez also dedicated the album to him, the only time she has done this to date for a romantic partner.

March 2003: Affleck says that Lopez is the only person who made him want a family

In a cover story with Vanity Fair, Affleck speaks at length about his relationship with Lopez, being especially candid about wanting to start a family with her.

“Jen and I want to get married for the reason everyone else does: we fell in love,” he said. “I'm in love; I want to have a family; and she's the only person I've ever met who made me entertain the thought of doing that. You know within 10 minutes of meeting Jen that she'll be a good mother. Though the heavens fall, she'll be a good mother.” 

Aug. 1, 2003: Gigli releases in theaters

"Gigli" - Premiere
Ben Affleck & Jennifer Lopez (Photo by Gregg DeGuire/WireImage)WireImage

Gigli releases to almost universally negative reviews, panned by critics and moviegoers alike. Dubbed the “worst movie” of the century by the Wall Street Journal, the critique leveled at the movie resulted in even greater media scrutiny on Lopez and Affleck.

In a 2015 interview with HuffPost Live, Lopez said that Gigli’s release was the start of a difficult period in her life. “I think the worst, probably lowest point was the whole Gigli era. It was pretty tough," she said. "It was a very badly reviewed film. I was in a high-profile relationship at the time that fell apart in a really bad way, and so the kind of mix of those two things and the tabloid press had just come into existence at the time, so I was like a poster child for that moment. I was in the tabloids every other week about how my life was falling apart. It was a tough time."

September 2003: Lopez and Affleck postpone their wedding

Three days ahead of their wedding, Lopez and Affleck postponed tying the knot in Santa Barbara because of the media frenzy surrounding the event. In a statement to People, the couple addressed their reasons for calling off the wedding.

“Due to the excessive media attention surrounding our wedding, we have decided to postpone the date,” Affleck and Lopez said 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.”

January 2004: Lopez and Affleck confirm their breakup

After 18 months together, Lopez and Affleck officially announced their breakup. Lopez issued a statement about the split: “Jennifer Lopez has ended her engagement to Ben Affleck. At this difficult time, we ask that you respect her privacy.” Affleck’s publicist refused to confirm anything about the actor’s personal life in response, saying, “It’s not happening from our side.”

March 2004: Jersey Girl releases in theaters

Jersey Girl releases in theaters to lukewarm reviews.

June 5, 2004: Lopez marries Marc Anthony

2007 Vanity Fair Oscar Party
WEST HOLLYWOOD, CA - FEBRUARY 25: Singer Jennifer Lopez (R) and husband singer Marc Anthony arrive at the 2007 Vanity Fair Oscar Party at Mortons on February 25, 2007 in West Hollywood, California. (Photo by Evan Agostini/Getty Images)Getty Images—2007 Getty Images

Four months after confirming her split with Affleck, Lopez marries singer Marc Anthony at her home in Beverly Hills. Lopez and Anthony met in 1998, while he was starring on Broadway in The Capeman; in her 2014 memoir, True Love, Lopez said that Anthony told her at their first meeting: "One day you’re going to be my wife."

In the memoir, Lopez also revealed that the relationship came about because she "sought out comfort in another person," following her split from Affleck.

"Marc came back into my life three days after I should have been at the altar saying 'I do' to another man," she wrote. In 2008, the couple welcomed twins Emme and Max.

June 2005: Affleck marries Jennifer Garner

85th Annual Academy Awards - Arrivals
HOLLYWOOD, CA - FEBRUARY 24: Actress Jennifer Garner and actor-director Ben Affleck arrive at the Oscars at Hollywood & Highland Center on February 24, 2013 in Hollywood, California. (Photo by Jason Merritt/Getty Images)Getty Images—2013 Getty Images

Affleck married his Pearl Harbor and Daredevil co-star Garner in Turks and Caicos in June 2005. The couple later welcomed their first child, Violet, in December 2005, followed by daughter Seraphina in September 2009 and son Samuel in February 2012.

May 2010: Lopez said that her relationship with Affleck "did suffer" because of the media

In an interview on the Graham Norton show, Lopez said that her relationship with Affleck was negatively impacted by media scrutiny.

“I love Ben, he's a great guy, but it was a lot for both of us to be under that type of siege for two years straight," she said. "We were on the cover of every magazine, every week, it was just a weird thing."

June 2011: Lopez and Anthony separate

One month after their seventh wedding anniversary, Lopez and Anthony announced their separation.

"We have decided to end our marriage," the couple said in a joint statement. "This was a very difficult decision. We have come to amicable conclusion on all matters. It is a painful time for all involved and we appreciate the respect of our privacy at this time."

April 2012: Anthony files for divorce

Anthony officially files for divorce from Lopez in April 2012, citing "irreconcilable differences."

January 2013: Lopez says she and Affleck are still in touch

During an appearance on Katie, Lopez told host Katie Couric that running into exes Sean Combs and Affleck at the Golden Globes wasn’t awkward.

“We run in the same circles," she said. "I do see them. The world doesn't know that I see them. I don't go, 'Hey, I ran into Diddy today.' I don't tweet that kind of stuff. But I do run into them. We talk and we email, more email than anything.”

Lopez also expressed happiness for Affleck’s Golden Globe wins for his film, Argo, calling it one of the “best pictures of the year,” and sharing that when he won, she gave him a standing ovation.

June 2014: Lopez and Anthony's divorce is finalized

Three years after they announced their separation, Lopez and Anthony's divorce is finalized.

November 2014: Lopez writes about Affleck in her memoir

Lopez didn’t shy away from writing about her relationship with Affleck in her 2014 memoir, True Love

“Ben and I split up at the moment when I thought we were committing to each other forever, it was my first real heartbreak, it felt like my heart had been torn out of my chest,” she wrote. “My way of anesthetizing the pain was different,” she wrote. “I sought out comfort in another person, tried to find someone who could make me feel loved and wanted in my loneliest hour.”

June 2015: Affleck and Garner announce their separation

Days after their 10th wedding anniversary, Affleck and Garner announce their separation.

"After much thought and careful consideration, we have made the difficult decision to divorce," the couple said in a joint statement. "We go forward with love and friendship for one another and a commitment to co-parenting our children whose privacy we ask to be respected during this difficult time. This will be our only comment on this private, family matter. Thank you for understanding."

April 2017: Affleck and Garner file jointly for divorce

Two years after they announced their separation, Affleck and Garner filed together for divorce.

October 2018: Affleck and Garner's divorce is finalized

Three years after they separated, Affleck and Garner's divorce is finalized.

February 2020: Affleck praises Lopez’s performance in Hustlers

In an interview with the New York Times, Affleck praised Lopez’s performance in Hustlers and makes the case that she should have been nominated for an Academy Award.

“She should have been nominated. She's the real thing,” he said. “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."

January 2021: Affleck ends relationship with Ana de Armas

Affleck began dating Ana de Armas, his co-star in the thriller film Deep Water, in 2020; de Armas confirmed their relationship in April 2020, when she posted a photo of the pair celebrating her birthday together on her Instagram. Their split was reported in January 2021; the breakup was confirmed by de Armas in a 2022 interview with ELLE, where she called the scrutiny following it, "horrible."

April 2021: Lopez ends engagement with Alex Rodriguez

31st Annual Palm Springs International Film Festival Film Awards Gala - Red Carpet
PALM SPRINGS, CALIFORNIA - JANUARY 02: (L-R) Jennifer Lopez and Alex Rodriguez attend the 31st Annual Palm Springs International Film Festival Film Awards Gala at Palm Springs Convention Center on January 02, 2020 in Palm Springs, California. (Photo by Rich Fury/Getty Images for Palm Springs International Film Festival)Getty Images for Palm Springs In—2020 Getty Images

In April 2021, Lopez ended her relationship with former MLB star Alex Rodriguez. The pair had dated since 2017 and gotten engaged in 2019. The pair confirmed their split to The Today Show: “We have realized we are better as friends and look forward to remaining so,” they said in a joint statement. “We will continue to work together and support each other on our shared businesses and projects. We wish the best for each other and one another’s children. Out of respect for them, the only other comment we have to say is thank you to everyone who has sent kind words and support.”

April 2021: Affleck is seen visiting Lopez at her home

Two weeks following the ending of her engagement, People reports that Affleck visited Lopez at her home in Los Angeles as a friend. 

July 2021: Lopez makes the relationship official on social media

Lopez and Affleck confirmed their relationship via social media after Lopez posts pictures of them together on a yacht, celebrating her birthday. In the photos, the pair seemingly recreate scenes from her music video, “Jenny From the Block;” eagle-eyed fans also noticed that a framed black and white photo of the pair in the background of one of the shots is from Affleck’s 2003 Vanity Fair cover shoot.

September 2021: Affleck and Lopez make their first red carpet appearance together in nearly two decades

"The Last Duel" Red Carpet - The 78th Venice International Film Festival
VENICE, ITALY - SEPTEMBER 10: Ben Affleck and Jennifer Lopez attend the red carpet of the movie "The Last Duel" during the 78th Venice International Film Festival on September 10, 2021 in Venice, Italy. (Photo by Pascal Le Segretain/Getty Images)Getty Images—2021 Getty Images

Affleck and Lopez appear together on the red carpet at the Venice Film Festival to promote his film, The Last Duel. It’s their first red carpet appearance together in 18 years.

April 2022: Lopez announces her engagement to Affleck in her newsletter

Lopez teased the announcement on social media, encouraging her followers to sign up for her newsletter, where she confirmed that she and Affleck are engaged.

“True love exists and forever is real,” she wrote. “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."

July 17, 2022: Affleck and Lopez marry in a surprise ceremony in Las Vegas

Affleck and Lopez surprised fans when they announced that they had tied the knot in a midnight ceremony in Las Vegas. Lopez recounted the details of the nuptials, calling it the “best night of our lives” in her newsletter: "We barely made it to the Little White Wedding Chapel by midnight," Lopez wrote. "They graciously stayed open late a few minutes, let us take pictures in a pink Cadillac convertible, evidently once used by the king himself (but if we wanted Elvis himself to show, that cost extra and he was in bed)." Lopez signed off her newsletter as “Mrs. Jennifer Lynn Affleck.”

July 2022: Affleck and Lopez honeymoon in Paris

Celebrity Sightings In Paris - July 26th, 2022
PARIS, FRANCE - JULY 26: Jennifer Lopez and Ben Affleck are seen at the Louvre Museum on July 26, 2022 in Paris, France. (Photo by Pierre Suu/GC Images)GC Images—2022 Pierre Suu

Affleck and Lopez celebrated their new marriage by honeymooning in Paris, where they were spotted visiting the Louvre and touring the River Seine.

August 2022: Affleck and Lopez marry again in Georgia

The couple married again in a more formal ceremony at Affleck’s estate in Georgia. In a series of dispatches from her newsletter, Lopez shared details about the ceremony and what the wedding meant to them as a couple.

“The 20 years between those dreams of youth and the adult world of love and family we embraced that day, brought more to this marriage than either of us ever could have imagined," she wrote. "We weren't only marrying one another; we were marrying these children into a new family. They were the only people we asked to stand up for us in our wedding party. To our great honor and joy, each one did. Some old wounds were healed that day and the weight of the past finally lifted off our shoulders. Full-circle—and not at all the way we planned it. Better."

In the years since their wedding, Affleck and Lopez have collaborated on multiple projects, including his 2024 Super Bowl Dunkin' Donuts commercial and her films, This Is Me...Now and The Greatest Love Story Never Told.

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Write to Cady Lang at cady.lang@timemagazine.com