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Jennifer Lopez & Ben Affleck during Daredevil Premiere - Arrivals at Mann Village Theatre in Westwoo...

J. Lo And Ben Affleck's Relationship Timeline Is Decades In The Making

It’s 2002 all over again.

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“Bennifer” is proof that it really ain’t over ‘til it’s over. After almost two decades apart — and multiple other weddings, divorces, births, and breakups — Jennifer Lopez and actor Ben Affleck are engaged and overjoyed to have rekindled their love.

In the years following their initial split in 2004 — what would become one of the most talked-about heartbreaks since Romeo and Juliet — each half of the uber-famous pair moved on multiple times over. Among other relationships, Lopez married singer-songwriter Marc Anthony and divorced in 2014, then dated and was engaged to baseball hall-of-famer Alex Rodriguez for nearly four years. Affleck married Jennifer Garner in 2005 before divorcing in 2018, and later dated actress Ana de Armas in 2020. But ever since Affleck was rumored to have visited Lopez at her L.A. home in April 2021, the resurrection of Bennifer has had fans begging for more.

But first, let’s back up. To understand Bennifer 2.0, we have to rewind the clock by 20 years — all the way back to the beginning. Read on for everything you need to know about Lopez and Affleck’s decades-long relationship timeline: the romantic highs, the devastating lows, and everything in between.

2001: Bennifer Meets On The Set Of Gigli

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It all started on the set of Gigli, a rom-com starring Lopez and Affleck that was released in 2003. When the two met, Lopez was still married to dancer Cris Judd, her second husband. (Her first marriage was to actor Ojani Noa in 1997.) Her divorce from Judd wouldn’t be finalized until 2003, after she and Affleck went public with their nascent relationship.

Years later, in 2016, Lopez spoke with People about the early days of Bennifer. "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." In the same interview, Lopez was candid about her feelings for Affleck. “I felt like … 'OK, this is it,'" she said about her first impression of the actor. "[But] sometimes I feel like what you think people are and how you see them when you love them is different than when they reveal later."

2002: Affleck Appears In Lopez’s Video For “Jenny From The Block”

Hardly anything is more iconically early aughts than Ben Affleck’s cameo in the “Jenny From The Block” music video — though Lindsay Lohan’s chunky blonde highlights in the 2003 remake of Freaky Friday are a close second. The video features plenty of PDA (shout-out to J. Lo’s pink bikini), plus surveillance camera footage and paparazzi snaps of the couple — a nod to the cultural craze surrounding their relationship.

Again, years later, Lopez spoke out about the pressure the couple was under, this time on the Graham Norton Show. “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 in 2010. "We were on the cover of every magazine, every week, it was just a weird thing. … Our relationship, I think, did suffer because of that."

November 2002: Affleck Proposes To Lopez

In late 2002, Affleck proposed to Lopez with a pink diamond ring that reportedly set him back a cool $2.5 million.

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January 2004: They Call Off Their Engagement

In the fall of 2003, the couple released a joint statement just days before what would have been their wedding ceremony. It read:

“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 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.”

But by January of the following year, the two were calling it quits, as reported by MTV. "I am confirming the report that Jennifer Lopez has ended her engagement to Ben Affleck," a Lopez spokesperson told MTV. "At this difficult time, we ask that you respect her privacy."

2004-2014: Lopez Moves On With Marc Anthony

In June of 2004, Lopez married her longtime friend, singer-songwriter Marc Anthony, just six months after her broken engagement. In 2008, Lopez gave birth to their twins, daughter Emme Muñiz and son Max Muñiz. Per Page Six, Lopez turned to Anthony for comfort in her darkest days following her breakup with Affleck — an experience that she chronicled in her 2014 book titled 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, per Page Six. "I sought out comfort in another person, tried to find someone who could make me feel loved and wanted in my loneliest hour. … Marc came back into my life three days after I should have been at the altar saying 'I do' to another man."

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2005-2017: Affleck Moves On With Jennifer Garner

But of course, it wasn’t just Lopez who seemed to have healed over. Affleck married actress Jennifer Garner in 2005, with whom he would have three children: daughters Violet and Seraphina Affleck, and son Samuel Affleck. In 2017, the couple officially filed for divorced, which was finalized in the fall of 2018.

2017-2021: Lopez & Affleck Date Alex Rodriguez & Ana de Armas, Respectively

After each of their very public divorces, both Lopez and Affleck began dating other beloved celebs. In 2017, Lopez and former New York Yankee Alex Rodriguez started a relationship that ended in April 2021 with a broken engagement. From 2020-2021, Affleck dated actress Ana de Armas.

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April 2021: Bennifer Rumors Begin To Spread

When a source reportedly tipped Page Six off about Affleck’s “platonic” visits to Lopez’s Los Angeles home, people began to speculate that those previously extinguished sparks were beginning to fly again. About their mysterious meetings, the source said: ​​"They are friends. They've never not been."

May 2021: Bennifer Is Spotted In Montana

Seventeen years after their breakup, E! News reported that Lopez and Affleck took off for Montana, where they spent a week together on vacation. Cue the media frenzy. E! News shared insight from several insiders who say, “Jennifer is happy.” “It's natural between them and the chemistry is unreal,” one source reportedly said. “They picked up where they last left off and are enjoying each other's company right now.”

Since their getaway, both E! News and People reported that the couple appears to be committed, having flown back and forth several times between Affleck’s residence in Los Angeles and Lopez’s in Miami. "Ben has been making the effort to make it work with their schedules. He's really making a huge effort," a source told E! News. "J. Lo thinks Ben has really stepped up and loves this version of him."

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June 2021: Sources Begin To Confirm A Brewing Romance

Entertainment Tonight reported that Lopez and Affleck are “very much a couple and have been telling friends that they're together,” according to a source. "[They] talked about the past and why things didn't work out. They are both hopeful about their relationship this time around and putting the effort in. They have both matured and are on the same page and it has been easy." But still, without statements directly from the pair, the stars kept fans speculating about the real nature of this renewed relationship.

July 2021: Lopez Makes It Instagram Official

That is, until July 2021 when the couple cranked up the heat: According to E! News, Lopez and Affleck’s families started spending more time together, sharing birthday parties and trips to Universal Studios. Affleck even spent the 4th of July at Lopez’s Hamptons home with her teenage twins. But the most exciting moment for fans came in the form of an Instagram post from Lopez herself. On July 25, in celebration of her 52nd birthday, she posted a steamy carousel of bikini pics with one heart-stopping surprise buried at the very end — a cozy, dreamy Bennifer smooch.

September 2021: Lopez And Affleck Made Their Red Carpet Debut

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After an Instagram official picture that sent fans into a frenzy, the biggest couple of the aughts finally made a red carpet debut at the Venice premiere of The Last Duel, which Affleck co-wrote and starred in. Their last red carpet event as a couple was for the Batman star’s movie premiere Daredevil in 2003, so this was a big deal, to say the least. The two shared plenty of sweet googly-eyed looks as they walked hand-in-hand for the cameras.

April 2021: Bennifer Got Engaged (Again)

Lopez revealed in her newsletter that her love Affleck proposed to her with an 8.5-carat green diamond ring while she was taking a bubble bath. After all the media circus surrounding their first engagement, the second time around was decidedly quieter and more intimate. She went on to say they are “two very lucky people — who got a second chance at true love.”

Looks like second time’s the charm.

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