Jennifer Lopez's Wedding To Ben Affleck Was 'Hard-Earned' & Her Dating History Is Messy

"We all have our paths to travel."

Contributing Writer
Ben Affleck and Jennifer Lopez in the early 2000s. Right: Affleck and Lopez at their wedding in 2022.

Ben Affleck and Jennifer Lopez in the early 2000s. Right: Affleck and Lopez at their wedding in 2022.

@jlo | Instagram, Courtesy On The JLo

Bennifer is finally a reality! After a few decades, some broken marriages and one almost-wedding, Jennifer Lopez seems to have finally found happiness with her new husband Ben Affleck.

"Years ago, we had no idea the road ahead would mean navigating so many labyrinths and hold so many surprises, blessings and delights," she wrote in her newsletter after the wedding. She added that she's finally found happiness, and it's the "hard-earned kind that's all the sweeter for the journey that came before it."

And it really was quite the journey.

To be precise, the Hustlers star has been married four times, gotten engaged six times and been in many relationships. But in the end she and Affleck seem ready to settle down, after a nearly 20-year break between when they first dated and when they finally married.

"We all have our paths to travel," she wrote in her newsletter.

Here's how she made it through a dating "labyrinth" to find him — and then find him again.

Bennifer 1.0

When Lopez first connected with Affleck on the set of the 2002 film Gigli, the actress-singer already had a complicated dating history.

She briefly married and then divorced producer Ojani Noa in 1997, had a “crazy, tumultuous relationship” with rapper Sean “Diddy” Combs, and was onto her second marriage to her former backup dancer, Criss Judd, at the time.

Gigli bombed at the box office and critics blasted Lopez’s chemistry with Affleck on screen, but it seems there were real sparks flying between them off-camera.

Lopez filed for divorce from Judd in June 2002 and confirmed rumors about her and the Good Will Hunting star by making their relationship official.

In the initial days of her relationship with Affleck, Lopez told Dateline that their love was based on being friends first.

The couple got engaged in late 2002 and were going to get married in September 2003. But days before the ceremony they canceled it, citing excessive media attention. By January 2004, their break up was official.

So how did things fall apart? In the years since their ill-fated relationship, they've both mentioned the intense media attention that surrounded them. It didn't help that their second film together, Jersey Girl, was also a flop.

Trying to move on

After Affleck and JLo split up, she married singer Marc Anthony in mid-2004 while he moved on with actress Jennifer Garner.

Neither relationship worked. Lopez even described her relationship with Anthony as a mere “Band-Aid on the cut” after Affleck, who she described as her “first real heartbreak.”

Lopez broke up with Anthony in 2011, then started dating backup dancer Casper Smart.

She later had a thing with Drake in late 2016 and into 2017.

However, the couple didn't last long and she moved on to New York Yankee star Alex Rodriguez. They got engaged in 2019, but they pushed their wedding date several times and eventually broke up in April 2021.

Bennifer 2.0

It's funny how things work out sometimes.

Lopez became single a few months after Affleck broke up with then-girlfriend Ana de Armas in early 2021. Soon, Lopez and Affleck were spotted out together on multiple occasions, and things got increasingly romantic until they made it Instagram official in July 2021.

The couple got engaged in April of 2022, married at a drive-thru Las Vegas wedding chapel in July and then threw a grand wedding for their friends in August.

"For us, this was perfect timing," JLo wrote in her newsletter. "Nothing ever felt more right to me."

So, the next time you use the phrase “meant for each other,” remember Bennifer as the ultimate example. After all, their story is nothing short of a fairy tale!

Apeksha Bagchi
Contributing Writer