It's … a lot.
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Once upon a time, Jennifer Lopez would meet her prince charming, Ben Affleck. And while their love story is anything but smooth sailing, the headlines and paparazzi photos might just be the most '00s way to tell a fairy tale about two of the most famous people in the entire world. And while you may think you know every last detail, here's everything from the first time they ruled the tabloids to the 2.0 version — and everything between. It's really just the story of a Boston boy and girl from the Bronx falling in love and realizing (after failed engagements and the trials and tribulations of respective high-profile divorces) that they're really meant to be.

Ben Affleck and Jennifer Lopez Are Engaged
Credit: Dominique Charriau/WireImage

2001

Affleck and Lopez famously meet on the set of Gigli. While the movie would act as a catalyst for their romance, it was a major box office flop. It's since become more of a punchline than a work of cinematic greatness, but for Ben and Jen, it'll always be the movie that brought them together.

September 2002

As if it wasn't enough to make one feature-length film together, the two of them make another one: Jersey Girl. There's a reason the two of them don't talk about these two films, ever. They're better left in the hazy memories of the '00s, but part of that might be because the headlines that surrounded Bennifer were more about their romance and not their art.

November 2002

Things are official when Ben puts a ring on it. He proposes to Lopez with a ring that has gone down in history: a 6.1-carat pink solitaire. At the time, J.Lo told Diane Sawyer that the proposal was "traditional but also in a very spectacular way, as of course Ben would do it ... it was very, very beautiful."

Not to be eclipsed by that stunner and the engagement news, Lopez decides to release something that's also gone down in history: the music video for "Jenny From the Block." Ben's in it, of course.

July 2003

The two attend the premiere of Gigli together, giving fans the red carpet moment they've been craving. Unfortunately, things seem a little tense. 

September 2003

Mere days before their wedding, the two call it off. In a joint statement, the two say that the media frenzy that surrounded their love story was something they just couldn't get over. Even though it never materialized, the wedding was going to include decoy brides, fake-out locations to throw off paparazzi, and the couple's famous friends.

"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," the statement read. "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

The engagement is officially over. Lopez releases an official statement via her representative that reads, "I am confirming the report that Jennifer Lopez has ended her engagement to Ben Affleck. At this difficult time, we ask that you respect her privacy."

Later that year, Lopez would go on to marry Marc Anthony — just months after the breakup with Ben. 

In her book, True Love, Lopez writes that Anthony "came back into my life three days after I should have been at the altar saying 'I do' to another man."

The two would go on to have two children together, Max and Emme.

Affleck starts dating his Daredevil co-star, Jennifer Garner.

June 2005

Ben and Jen Garner get married in Turks and Caicos. They would eventually have three children together: Violet, Seraphina, and Samuel.

July 2011

Lopez and Anthony file for divorce, but it wouldn't get finalized until June 2014, according to the L.A. Times.

January 2015

During a sit-down with HuffPost Live, Lopez says that she has "no regrets" about her relationship with Affleck. 

I would do it all over again, I think. I really would. Even the relationship part. I just feel like everything is part of your story and your journey and is meant to be and helps you grow if you're willing to look at it, and I'm willing to look," she said. She even mentioned the ill-fated Gigli, saying that 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."

June 2015

Affleck and Garner separate.

In February 2020, Ben said his divorce from Garner was his "biggest regret."

October 2018

Ben and Jen Garner's divorce gets finalized.

February 2020

During an interview, Affleck tells the New York Times that Lopez should have been nominated for her work in Hustlers, saying, "She should have been nominated. 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 fucking baller."

And in a sit-down with Diane Sawyer, he explained that in five years, "I would love to have a relationship that is deeply meaningful and one to which I could be deeply committed … Five years from now, Ben Affleck is sober and happy and sees his kids three and a half days a week and has made three or four movies that are interesting to him. I directed two [movies] that he is hopefully proud of and is in a healthy, stable, loving, committed relationship."

May 2021

Bennifer 2.0 basically breaks the internet. The two are seen together in Montana and it all happened via email, apparently.

Page Six reports that the couple's "public comeback romance" was supposed to happen in a "tightly controlled" way, but the paparazzi snapshots ruined all those plans.

"He stayed at her house [in April], and she was planning to make an announcement that they are back together on Instagram," a source said. "It's all about timing with her. These are people who don't like to be alone, and she really likes him. They have a long history there."

Jennifer Lopez and Ben Affleck
Credit: Getty Images

June 2021

Sources go on to tell E! News that Lopez "is packing up her Miami rental" and getting ready to move to L.A. with her twins to be closer to Ben and his children.

July 2021

In an interview with Zane Lowe on Apple Music 1, Lopez says that she's happier than ever. Considering what went down with her failed engagement to Alex Rodriguez, fans are ecstatic.

"I'm super happy … I know people are always wondering, How are you? What's going on? Are you OK? This is it. I've never been better. And I want my people who care about me, because I care about them so much, to know that I've really gotten to a place in my life where I'm great on my own," she said. "And I think once you get to that place, then amazing things happen to you that you never imagine in your life happening again. And so that is where I'm at. And I love all the love that's coming my way right now and all of the good wishes. And I just want everybody to know that it's the best time. It's the best time of my life."

Us Weekly adds that the process of blending their families is no problem at all.

"Ben and Jen are spending almost every night together when they're not working ... they plan on moving in together very soon," a source said. "As far as Jen sees it, she and Ben have their whole lives now to set things up in a comfortable way. She intends to be an involved stepmom who's there for Ben in that area, plus she'll want him to make the same effort with her and Marc's kids."

The two go Instagram-official with a kiss on Lopez's 52nd birthday.

September 2021

For the first time since Gigli, the two make a red carpet appearance together at the 78th Venice International Film Festival. And a few days after that, they attend the Met Gala together.

October 2021

The red carpet moments continue when Lopez attends the premiere of The Last Duel with Affleck. She also shows up to support him at the premiere of The Tender Bar later in 2021.

Jennifer Lopez Ben Affleck

December 2021

The trifecta is complete. After a red carpet and the Met, the two are courtside at a Lakers game and, of course, make a cameo on the kiss cam.

April 2022

Bennifer got engaged — again! Jen announced the happy news on her email newsletter, On The J.Lo, on Friday (April 8) with a glimpse of her new diamond ring that's a soft green color. In a video shared to Twitter, J.Lo directed fans to her website, explaining that she had "a really exciting and special story to share" with them. "Major announcement!!!!" she captioned the clip.