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.

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.


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.

August 2002: Spotted in West Hollywood

The two head to a party together.

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: "Jenny From the Block"

The actor stars in J.Lo's music video.

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.

March 2003: Spotted in Beverly Hills

The two show some PDA as they leave a gym.

April 2003: Paris Vacation

The two head to their hotel in the French capital.

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 flops at the box office.

September 2003

The two pay a visit to the Liberty County courthouse in Georgia.

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.

Early May 2021: VAX LIVE Concert

The two are spotted separately at the event in Los Angeles, days after Ben is seen at J.Lo's home in the city.

May 2021: First Pics of Bennifer 2.0

In early May 2021, Jen and Ben are photographed vacationing together in Montana, where he has a home. It marked the first time they were photographed since ending their engagement in 2004.

July 2021: Family Day at Universal Studios

J.Lo and Ben bring her twins, Max and Emme, and his son Samuel to Universal Studios Hollywood. It marked the first time J.Lo or her family have been spotted with any of the actor and ex-wife Jennifer Garner's three children. Ben had joined J.Lo and her kids at a birthday dinner for her sister weeks earlier.

July 2021: Hamptons Love

The two take their rekindled romance to the Hamptons in New York, where J.Lo has a house, over the Fourth of July weekend.

July 2021: Happy Birthday Jennifer

Ben and Jen party at her 52nd birthday party at L'Opera restaurant in St Tropez, France, where she sings along to her 2002 hit "Jenny From the Block."

September 2021: Return to the Celebrity World

Following many public but casual appearances, including with the actor's three kids and J.Lo's twins, plus several national and international trips, Bennifer officially make their return as a couple in the celebrity world when they attend the 2021 Venice Film Festival, their first industry event since they rekindled their romance.

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! 

View More Photos From Jennifer Lopez & Ben Affleck: Romance Rewind