The Jennifer Lopez and Ben Affleck relationship timeline: movies, 'I do's' and everything in between

The Jennifer Lopez and Ben Affleck resurgence has sent us back in time. Cue the  2000’s nostalgia!

In reality, 20 years have passed, yet Bennifer's rekindled romance seemed effortless, so much so that is has caused many of us to question if getting back with an ex is actually a good idea. (Who would've thunk it?)

Now, fans are gearing up Jennifer Lopez: Halftime's debut on June 14, one of the most anticipated Netflix releases this month. In honor of the buzzy documentary, we've conveniently outlined her relationship timeline with the Good Will Hunting actor for those who are curious how it all unfolded...twice. 

Jennifer Lopez and Ben Affleck relationship timeline

2002

Remember Gigli? Chances are that's a negative, considering it was a bomb box office. Though the gangster film did not land on the canon of best JLo movies, it did bring Lopez and Affleck together. 

The two started out as friends while on set—per the singer's claims—but things quickly took a turn for the romantic. Lopez filed for divorce from Cris Judd in June 2002, and by November of that year, she and Affleck were newly betrothed, according to US Weekly. 

And of course, those who were known to blast "Jenny from the Block" on their Walkman will remember the super-sexy Affleck cameo in the video while aboard a yacht. 

2003

The two were on the fast track down the altar, but ultimately, their California ceremony in 2003 did not take place as planned, and both cited the media circus around their love as the reason for its demise. 

In a statement, per Elle, the couple said: "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."

Years later, the split still had an impact on the super-star. 

"It was probably my first big heartbreak," Lopez confessed to Maria Shriver in 2014 while on the TODAY Show. 

Likewise, Affleck reflected on their breakup in 2012 and noted, "I think Jen and I made a mistake in that we fell in love, we were excited and maybe too accessible," while on Live. 

The in-between years

The two managed to stay on fairly healthy terms, despite pursuing new relationships after their split. Though Affleck did admit to regretting his appearance in the "Jenny from the Block" music video, he had gone on to to praise JLo's work ethic and talent. 

For her part, Lopez noted her feelings for Affleck in her book, True Love, and even threw in a couple of jokes here and there, particularly while addressing Affleck's enormous back tattoo while on Watch What Happens Live! in 2016, according to US Weekly.

The rekindling in 2021

In honor of the star's 30 years of fame, InStyle had a huge cover story dedicated to Lopez, and everyone in her life—from her exes to Michelle Obama—commented on the singer's impact in the business. 

"Where are you keeping the fountain of youth? Why do you look the same as you did in 2003, and it kind of looks like I'm in my 40s…at best," Affleck joked to the outlet. 

Our attention piqued for sure, but no one thought too much of it at first. 

What truly made us curious was a result of Lopez's broken engagement: following the shocking Jennifer Lopez and Alex Rodriguez split in 2021, fans quickly pivoted their attention to the Boston-born actor and Bronx native's time together in Montana. "Are JLO and Ben Affleck dating," we all wondered. 

As it turns out, their downtime in the Treasure State proved to be the start of round two. Shortly thereafter, the two went Instagram official.  

Then, they went red-carpet official for Affleck's film, The Last Duel at the Venice Film Festival. 

April 2022

The engagement heard 'round the world: on April 9, 2022, JLo shared that she and Ben were engaged.

It's been a whirlwind for sure, but we're fairly certain these two will continue to make headlines for the next 20 years and beyond.