Will Bennifer Last? A Timeline of the World’s Favorite Rekindled Romance

Bennifer is back after twenty years, and they're having more fun than ever. Check out a timeline of this iconic couple's wild road to love. Do you think they'll go the distance this time?
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Can you believe that twenty years ago, we were in the year 2001? It feels like just yesterday that Britney Spears was dancing at the VMAs with a caged tiger to her side and a python around her shoulders. NSYNC was tapped to perform at Super Bowl XXXV at the height of their fame, Destiny’s Child was on the rise, and the country was still in awe after the release of Harry Potter and the Sorcerer’s Stone.

Bennifer walked so Brangelina, TomKat, and Kimye could run. So what happened to their love?

Looking back on the pop culture climate of twenty years ago, one has to marvel at all the ways the world has evolved. But what’s even more fascinating is the way some aspects of life never change–and apparently, Jennifer Lopez and Ben Affleck’s affection for each other is one of those constants.

LOS ANGELES - JUL 23: Jennifer Lopez and Ben Affleck arrives for the ÔGigliÕ Hollywood Premiere on July 23, 2003 in Westwood, CA

I still can’t tell if Bennifer being back after twenty years of absence is part of a collective, wishful hallucination by society or if it’s the real deal.

Their rekindled romance seems too fairytale-esque to be true, but the two really do seem happier than ever. Let’s take a look back at Bennifer’s romance timeline to see where they might go from here.



After meeting on the set of Gigli, Jennifer and Ben were inseparable. The tabloids were dominated by stories of their romance. Ben even accompanied Jen in the iconic music video for her 2002 single Jenny From the Block.

The Oscar-winning actor and the rising pop star were Hollywood’s it couple without a doubt. In fact, they were the first high-profile couple that tabloids and fans referred to as a singular entity: Bennifer.

Bennifer walked so Brangelina, TomKat, and Kimye could run. So what happened to their love?


Ben and Jennifer had planned to get married in September of 2003. They were so in love, but the media attention seemed to burn them out. Neither of them had anticipated how difficult it would be to be in the public eye at all times.

They ended their engagement in 2004 with respect, but also heartbreak on both sides.


From 2004-2011, Jennifer was married to singer Marc Anthony, with whom she had her kids, Max and Emme. She also dated her backup dancer, Casper Smart, from 2011-2016.

Meanwhile, Ben found love with actress Jennifer Garner, and the pair had three kids together. They were married from 2005-2018, their split coming around the time J.Lo began a relationship with baseball player Alex Rodriguez.

We know how much Jennifer and Ben love their respective children, and it seems it might have been destiny that they had to separate for some time in order to raise the families they were meant to have.

But Jennifer did say something highly prophetic and hopeful about Bennifer at the time of their devastating 2003 split: “I think different time, different thing, who knows what could’ve happened?”


For a while there, it seemed like the dream of Bennifer was dashed forever. J.Lo and A-Rod were on their way to marriage, and it seemed like Jen had found her perfect match. The relationship seemed like it was going to last forever… until the pair announced in April of 2021 that they had split.

But almost as abruptly as J.Lo and A-Rod ended, Jennifer was seen hanging out with an old friend that nobody expected to come back into the picture: Ben Affleck. Did we dare hope these two early-2000s sweethearts would try out a romantic relationship again?

Bennifer on J.Lo’s 52nd Birthday / Instagram – @jlo

After twenty years apart from each other, it didn’t take long at all for Jen and Ben to win back each other’s hearts– as well as the attention of the entire world.

Now we are once again indulging in the dream of the early 2000s. Bennifer is back, and while there’s no telling if this rekindled romance will end in marriage on the second try, we couldn’t be happier for these two.

After all they’ve both been through, maybe the constant media attention that mired their relationship when they were young up-and-comers in Hollywood will be easier for them to take.

J.Lo just celebrated her 52nd birthday by taking a luxurious boat ride with her old/new flame, and these two seem like they’re going to stick together for a while. I know I hope to see Bennifer go the distance, but if history has taught us anything, it’s that no celebrity couple is a sure thing.

What do you think: Will Bennifer last this time?