The Complete 20-Year Timeline of the Bennifer Saga

Bennifer’s back, baby. Photo: Kevin Winter/Getty Images

It’s a Hollywood love story 20 years in the making. Ben Affleck and Jennifer Lopez rekindled Bennifer over a week in Montana this May, now that the stars have realigned and they’re both single at the same time … again. Over less than two years, from 2002 to 2004, their glamorous romance fueled early-tabloid culture, set the standard for ship names, then fizzled out faster than it began. Within a year, they were married to Jennifer Garner and Marc Anthony, respectively, occupying celebrity news with other people. Now, they’re back to their old Y2K ways. Their 2021 reunion has inspired endless gossip (bless the “sources”), not to mention several essays devoted to our nearly two-decade-long cultural obsession with this perfectly odd couple. Sorry to everything Ben Affleck stands for, but no film could begin to encompass the daily drama (and hilarity) of his real life. Catch up on Bennifer with this timeline of their relationship across the ages.

‘Co-stars’ and ‘friends’

Early 2002: Pop star Jennifer Lopez and Hollywood golden boy Ben Affleck meet on the set of Gigli while Lopez is married to her second husband, Cris Judd. Where else does Ben Affleck meet any of his girlfriends at this point? Raya doesn’t exist yet.

April 2002: Affleck takes out a full-page ad in trade magazines to compliment J.Lo, which doesn’t exactly say “bestie vibes only.” “It has been nothing but an honor and a pleasure to work with you,” it reads, in part. “I only wish I were lucky enough to be in all your movies.” Signed: “With love, respect, and gratitude, Ben Affleck.”

July 24, 2002: “Co-stars” and “friends” Jennifer Lopez and Ben Affleck are seen kissing and cuddling at a surprise-birthday party for the Leo superstar, one of the first events marking the start of their relationship with the tabloids.

July 26, 2002: J.Lo files for divorce from husband No. 2 after a month of separation (but that’s a story for a prequel timeline).

August 5, 2002: People magazine pays $75,000 for nine photos of J.Lo and Ben Affleck riding in a Bentley convertible, including one where they “lip-lock.”

November 5, 2002: MTV’s TRL premieres the music video for “Jenny From the Block,” a Y2K mood board starring Bennifer, combining J.Lo’s roots with her new movie-star lifestyle. Ben famously leans over and kisses her butt while they sun on a yacht (yes, this relationship explains his early 2000s tan), and nobody here can blame him, really.

Benny From the Block

The Ass-Smooch Heard Round the World

While kissing a booty long-rumored to be worthy of a $27 million insurance policy is on many of our bucket lists, in 2008, Affleck said the music video was his “big regret” of the relationship. See, the song is a megabop asserting J.Lo’s street cred, but the video itself is about the public’s obsession with the couple, told through the literal lens of the paparazzi following them from lunch to the yacht to the gas station and home, hoping to catch intimate moments between Jenny from the block and Boston’s hometown hero. But worshipping J.Lo’s backside was a performance choice all his own. The video went early-2000s viral, so ultimately, exposing themselves to comment on their overexposure backfired. And we’re left with a grim yet sexy prediction of their hyperpublic downfall that even J.Lo tried to get removed from MTV and VH1 in 2004.


November 2002: By November, they’re engaged. Within months of her separation, Ben proposed to Jen at his mother’s house in Boston. “It’s just a blanket, a quilt of rose petals, all over the whole entire house,” Lopez remembered in an ABC exclusive interview with Diane Sawyer, announcing their engagement. “So many candles, and vases, bouquets. And my song ‘Glad’ was playing … I walk in and I was just, like, overwhelmed. I wasn’t expecting it, and I was just like, ‘Oh my God.’” The ring, a pink diamond the size of Affleck’s head, would go down in pop-culture monogamy history.

Photo: Kevin Winter/Getty Images

March 2003: Affleck denies any notion that he acted on his feelings before J.Lo and Judd separated. “That is absolutely not true,” he tells Vanity Fair. “It goes against the fundamental code I believe in and live by: being honest, doing things with which I can live, rather than be ashamed of — doing esteemable things.” The couple never officially says when they got together, but they do emphasize their innocence.

July 17, 2003: Affleck reportedly pays a visit to a strip club in Vancouver, where he was recording Paycheck, hours after their intimate Dateline interview aired. The National Enquirer claimed he cheated on her with at least one woman and that the encounter might be on tape. Shortly after, reports start to suggest Lopez has stopped wearing her million-dollar ring. “What they put in the paper is not what happened, so it doesn’t matter,” she would tell W magazine later that summer, in an interview that came out in October. “But watching that get so blown out of proportion, I was like, Wow, so this is where we’re at: You can’t walk into a place and hang out with a couple of friends without it turning into a national scandal.” Ben himself denied cheating via a spokesperson and reportedly considered suing the Enquirer.

August 1, 2003: Gigli is dead on arrival a box-office and critical bomb, with a worldwide gross of $7.7 million against a $75.6 million budget — and so are the vibes between the supposed “It” couple at the premiere, fueling suspicions that the romance is dying down.

Bennifer at the Gigli premiere. Photo: Jeff Kravitz/FilmMagic

September 13, 2003: The day before the highly anticipated nuptials — America’s version of a royal wedding before Kim Kardashian made it a regular occurrence — Bennifer releases a joint statement via a spokesperson postponing the wedding.

Due to the excessive media attention surrounding our wedding, we have decided to postpone the date. 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.

September 14, 2003: A wedding for 400 in Santa Barbara, California, does not happen in spite of reports.

January 23, 2004: “Dumped,” reads the headline from the Chicago Tribune. Jennifer Lopez officially ends the discourse (and her relationship) in a statement to the Associated Press. “I am confirming the reports that Jennifer Lopez has ended her engagement to Ben Affleck,” a rep states. “At this difficult time, we ask that you respect her privacy.” That did not happen.


March 26, 2004: Jersey Girl, Bennifer’s second try at being a movie-star couple, directed by Kevin Smith, the man who now claims he gave them the nickname “Bennifer,” premieres. Though it’s mostly remembered for crashing and burning as hard as the relationship had, I can’t be the only 2000s kid straight-up traumatized by Gertie (Lopez) dying during childbirth??? And then they ask why millennials aren’t having babies.

June 5, 2004: J.Lo marries Marc Anthony, whom she first dated back in 1999 after they collaborated on “No Me Ames.” “We thought that this was where everything was supposed to lead, that we were meant to end up together,” wrote Lopez in her 2014 book, True Love. “All the heartache and pain of my recent breakup couldn’t have been for nothing, could it? Maybe I had to go through the bad so I could end up with the person I was meant to be with all along.”

October 23, 2004: Ben Affleck and Jennifer Garner make their first public appearance as Bennifer: The Sequel at the World Series. They first met on the set of Pearl Harbor in 2000, but Affleck would later say they fell in love in 2002, on the set of Daredevil, while they were both in other relationships. (Again, that’s a timeline for another day.)


Two marriages and some babies

2005–2018: An entire decade and some change passes by in a Dunkin’ Donuts coffee-buzz haze. Affleck and Garner marry in 2005, then welcome three kids: Violet in December of that year, Seraphina in January 2009, and Samuel in February 2012. Meanwhile, J.Lo and Marc Anthony have twins, Emme and Maximilian, in 2008, and dramatically divorce three years later in 2011. Not to be outdone, Affleck and Garner go on to divorce in 2018 and Affleck rebounds with a massive dragon tattoo. Around 2017, J.Lo briefly has a thing with Drake, who himself boasts a cornucopia of famous exes that would derail this timeline. But, as J.Lo also told People in 2016 of her past relationship with Affleck, “I think different time, different thing, who knows what could’ve happened, but there was a genuine love there.” Interesting you would say that …

Intermission II

A Moment for BenAna and J-Rod

March 9, 2019: After dating for two years, former Yankee Alex Rodriguez proposes to J.Lo with the kind of ring that has something to prove (because it does), and the world begins to anticipate another J.Lo–sized royal wedding. Yes, we have Meghan Markle now, but let’s be honest, her wedding was modest compared to what J.Lo could cook up.

March 8, 2020: Deep Water stars Ben Affleck and Ana de Armas take a trip to her home country, Cuba. When they get back, they quarantine and perform for paparazzi together in Los Angeles, confirming their romance.

December 2020: Lopez talks about having to postpone the wedding twice during the coronavirus pandemic on Access Hollywood. “There’s no rush, we’re good, everything’s cool and it’ll happen when the time is right,” she says without an ounce of fear.

January 18, 2021: The pandemic does not end, but BenAna does. Two days later, J-Rod attend the Biden-Harris inauguration and any marital strife is drowned out by J.Lo’s most patriotic “Let’s Get Loud” yet.

February 3, 2021: Rumors that A-Rod is cheating with Southern Charm star Madison LeCroy begin to flood the tabloids like Miami during the rainy season. LeCroy tries to clarify by saying she and Rodriguez never met in person and “[have] never been physical … never had any kind of anything.”

March 12, 2021: Sources tell “Page Six” that A-Rod and J.Lo have split up.

March 14, 2021: Except, apparently, sources need to mind their own goddamned business. “All the reports are inaccurate,” reads a joint statement from the couple to TMZ. “We are working through some things.”

April 5, 2021: In an InStyle cover honoring J.Lo with praise from her friends and collaborators, both Marc Anthony and Ben Affleck call her the hardest worker they know while A-Rod isn’t quoted.

April 15, 2021: Okay, sources might have been onto something. “We have realized we are better as friends and look forward to remaining so,” the couple tell Today in another joint statement. “We will continue to work together and support each other on our shared businesses and projects.”

Bennifer, Back on the Block

April 30, 2021: The public gets its first glimpse of Bennifer in 17 years, as Affleck is seen going back and forth from her Los Angeles mansion. In that time, they’ve gotten hotter and richer, while the internet has gotten more adept at exposing celebrities. What could go wrong? For starters, their reunion comes with a big ol’ disclaimer that they’re friends. “They’ve never not been,” a source tells “Page Six.”

May 2, 2021: Ben and Jen spend the week in Montana, arriving back in L.A. on Saturday, May 8, sources tell anyone who would listen. “It’s natural between them, and the chemistry is unreal,” a J.Lo source told E!, also confirming that he reached out to her. “They picked up where they last left off and are enjoying each other’s company right now.” Aren’t we all?

May 19, 2021: “Jennifer is still very excited about how things are going,” an insider tells People, adding that Bennifer are “making plans to see each other” and are “in touch every day” while Lopez returns to Miami. And the cycle restarts!

May 23, 2021: Per TMZ, Ben Affleck arrives in Miami wearing several layers too many and is later seen smoking a cigarette on the balcony at the same waterfront mansion as J.Lo. On his wrist appears to be the watch he wore in “Jenny From the Block” way back when. Is this an Easter egg just for us?

Meanwhile, A-Rod is stepping “into a new beginning,” according to an new Instagram Story. “I am remaining patient and know that this new phase of my life is coming,” he posts. It’s a new dawn, a new day, and Bennifer is feeling good.

May 24, 2021: Ben and Jen both worked out at a Miami Beach gym on Monday, sharing a kiss in between separate private sessions, per In Touch. Apparently, no gym bros caught it in the background of their mirror selfies. Rude!

May 31, 2021: After meeting up with another ex, Marc Anthony, in Miami, J.Lo returned to Los Angeles and into the arms of Ben Affleck. The duo was photographed cuddling as they arrived at the Pendry Hotel in West Hollywood for dinner. Okay, now kiss …

June 13, 2021: After weeks of the world clinking their spoons to their glasses, they kissed! And what happens at Nobu, ends up in “Page Six.” Jennifer Lopez and Ben Affleck were photographed kissing again for the first time on Sunday at a function for her sister’s 50th birthday, sources say. In footage from the event, J.Lo’s 13-year-old twins, Max and Emme, could also be seen. According to People spies, Ben and J.Lo held hands under the table as well. “Ben and her kids seemed comfortable together,” the source told People. “The kids kept chatting with Ben. Ben seemed great. He was smiling and laughing. They ordered a lot of food to share. Ben had a Diet Coke.” Just like 20 years ago, Bennifer is going full speed.

July 24, 2021: Feliz Cumpleaños to the unaging Jennifer Lopez. She celebrated it just like she spent her b-day in 2002: by “kissing” Ben Affleck. The 52-year-old posted a slideshow of photos to Instagram, including one where she and Affleck are kissing. Bennifer is Instagram official, and it only took 19 years and the creation of the app.

July 25, 2021: And what would Bennifer 2 be without an encore ass rub? Y’all went online and begged for the sequel, so don’t be mad when they throw in a little fan service. Ben Affleck was once again snapped giving J.Lo’s ass a touch on a yacht in Monaco (not far from ex A-Rod), recreating a scene from the 2002 “Jenny From the Block” music video inadvertently or not. The on-the-nose ass grab seems to reveal a cog in the celebrity machine, shamelessly relying on nostalgia and boredom to stay relevant. If Bennifer 2.0 is just an act, at least they’re hitting their cues.

July 26, 2021: J.Lo wears a “Ben” necklace, in case it wasn’t clear. Almost wish Affleck started wearing a “Jen” necklace, just to confuse the tabloids.

Bennifer takes Venice Film Festival. Photo: Filippo Monteforte/AFP via Getty Images

September 10, 2021: Affleck and J.Lo end their summer of love at Venice Film Festival, making waves in the water taxis, on a balcony, and, finally, on their first red carpet since reuniting. Nineteen years since they first appeared as a couple at the Maid in Manhattan premiere, the couple arrived together for the premiere of Affleck’s The Last Duel and assumed those familiar positions on the red carpet, gazing deeply at one another and sharing kisses like we’re not watching. Cameras flashed, time folded in on itself. Lopez comes directly for Oscar Isaac’s viral red-carpet flirtation earlier this fest with intense eye contact and the raw sexual magnitude of a nude lip. If this is Bennifer acting, it’s better than any movie either of them have been in.

September 13, 2021: Thanks to Lopez and Affleck, making out with masks on is now Met Gala behavior.

March 21, 2022: Bennifer reportedly become homeowners together. Things have been a little quite on the Bennifer front — while promoting her movie Marry Me, J.Lo said she was “trying not say too much” about her rekindled relationship. But rest assured that the couple is still going strong, to the tune of a $50 million mansion in the Bel-Air neighborhood of Los Angeles.

Wedding Bells Are Ringing

April 8, 2022: Lopez announces via her On the J.Lo newsletter that she has gotten engaged to Affleck. In a short video, she tearfully looks at the giant green ring on her finger. The clip was set to the sound of her whispering “You’re perfect” in her song “Dear Ben,” which was released in the first year of their relationship. That’s what we call a full-circle moment, folks.

July 17, 2022: They did it, folks. Nineteen years after they chose not to get married the day before the wedding, Bennifer are married, and J.Lo announces it in her newsletter. This time, though, they did it “in a drive through in Las Vegas at twelve thirty in the morning” with kids, a far cry from the festivities of their first intended wedding. She notably signs the letter from “Jennifer Lynn Affleck,” so move over J.Lo, J.Aff is in the building. “In the end it was the best possible wedding we could have imagined,” writes J.Aff. “One we dreamed of long ago and one made real (in the eyes of the state, Las Vegas, a pink convertible, and one another) at very, very long last.” We hope the happy couple got Dunkin’ Donuts on the way home.

The Complete 20-Year Timeline of the Bennifer Saga