Jennifer Lopez and Ben Affleck Are Engaged: Relive Their 20-Year Romantic History

Jennifer Lopez and Ben Affleck are engaged for a second time, she shared on April 8. Take a look back at the couple's love story, which began more than two decades ago.

By Lindsay Weinberg Apr 09, 2022 3:49 AMTags

Marry me, marry me, say "Yes"! Jennifer Lopez and Ben Affleck are giving their engagement another go. 

J.Lo shared that she and Ben are planning to get married, nearly 20 years after they called off their last engagement.

The singer revealed the happy news with a video on her website on April 8, showing off her ring with a stunning green stone. She teased a "personal" announcement on Instagram, writing, "I have a really exciting and special story to share." 

The couple has been going strong since May 2021, but fans have been shipping Bennifer since 2001, when they filmed the movie Gigli together. They started dating and got engaged in November 2002, with her revealing her 6.1-carat pink diamond ring. It wasn't meant to be, however, as the two ended their engagement in 2004. 

That all changed last year, when the pair reconciled following her split with Alex Rodriguez. Jennifer and Ben reunited at the VAX LIVE Concert and then set off for a cozy getaway to Montana that sparked their revived romance.

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Jennifer Lopez Through The Years

Since then, it seems they've been bringing their families together as one, with several outings with their children from previous relationships. The Batman star shares kids Violet, Seraphina and Samuel with ex-wife Jennifer Garner, while J.Lo shares 14-year-old twins Max and Emme with ex-husband Marc Anthony. She was also previously married to Cris Judd and Ojani Noa.

JosiahW / BACKGRID

With 20 years of history between them, J.Lo told The New York Times that she learned a lot from her relationship with Ben the first time around.  

Her biggest takeaway? "To hold it sacred," she said of their bond. "You have to do what feels good to you all the time. But at the same time, you learn from the past, you do things better the second time. There's a part of it that, yes, we're together. But there's a part of it that's not, you know, being so open the way we were when we were so young and in love many years ago."

As for Ben, he's called the new relationship a "beautiful" story, telling WSJ. Magazine in December, "One of the things I really value across all facets of my life now is that it was handled in a way that reflected that. My life now reflects not just the person that I want to be, but the person that I really feel like I am."

Keep reading to take a look back at Jennifer and Ben's love story.

December 2001: Filming Gigli

The two prepare to film a scene for the movie in West Hollywood. The couple met on the set of the film.

October 2002: Spotted in Beverly Hills

The two are spotted in the city.

November 2002: Filming Gigli and Engagement

The two film the movie on Will Rogers State Beach in Los Angeles. That month, the actor proposes to the actress with a 6.1-carat pink diamond ring.

November 2002: Filming Jersey Girl

The two film the movie in New York City.

November 2002: Leaving MTV's TRL

Is there anything more '00s than both Bennifer 1.0 and TRL?

December 2002: Red Carpet Debut

The two make their red carpet debut as a couple at the premiere of her film Maid in Manhattan.

January 2003: Sundance

The two bundle up at the Sundance Film Festival in Utah.

February 2003: Daredevil Premiere

The two appear at the premiere of Daredevil, starring Ben as the superhero.

February 2003: Daredevil Premiere

The two appear at the premiere of Daredevil, starring Ben and future ex-wife Jennifer Garner.

March 2003: Oscars

The two attend the Academy Awards together.

May 2003: Basketball Game

The two sit courtside at a Los Angeles Lakers game.

July 2003: Canada Trip

The two film a Dateline interview for NBC in Vancouver.

July 2003: Gigli Premiere

The two appear at the premiere for their movie in Westwood, Calif.

August 2003: Gigli Is Released

...it flops at the box office.

September 2003: Wedding Is Off

The two postpone their wedding. No future date is given.

October 2003: Baseball Date

The two are seen at a Boston Red Sox game. The team is Ben's favorite.

January 2004: It's Over

The two end their engagement.

September 2021: Red Carpet Royalty

They're baaaack. On Sept. 10, the couple makes their first red carpet appearance in 18 years at the Venice Film Festival premiere of The Last Duel

September 2021: Look of Love

There's no denying J.Lo makes for a stunning plus-one! 

September 2021: Back to the Stage

Ben supports J.Lo at the 2021 Global Citizen Live event in New York City, where she performed onstage. It marked her first music gig since she performed at VAX LIVE in May, where the actor also appeared onstage separately, fueling rumors of a rekindled romance.

September 2021: Met Gala Debut

The two attend the Met Gala together for the first time.

October 2021: PDA at Premiere

Jen and Ben put on a sizzling display on the red carpet at the premiere of his film The Last Duel in New York City.

April 2022: Engaged Again!

Jennifer confirmed her engagement to the Gone Girl actor with a video posted to her On The JLo site, revealing a glimpse of her beautiful engagement ring with a green stone.

July 2022: Married!

On July 16, Jennifer and Ben tied the knot in a surprise ceremony at A Little White Wedding Chapel in Las Vegas.

July 2022: Post-Wedding Trip to Paris

The two vacation with her twins and two of his kids in the French capital soon after their wedding.

June 2023: Red Carpet Fabulous

J.Lo steps out with Ben in support of his movie The Flash.

February 2024: This Is Them...Now

Jennifer release This Is Me... Now, an album about her relationship with Ben. The record is accompanied by a musical film titled This Is Me... Now: A Love Story and the documentary The Greatest Love Story Never Told.