Jennifer Lopez's Divorces, Canceled Engagements and Breakups — Why Her Many Relationships Failed

Real-life couples don’t just magically live happily ever after, and multi-award-winning singer and actress Jennifer Lopez knows it firsthand. She’s been married three times and called off two engagements so far.

Lopez has been searching for love most of her adult life, but she’s currently back on the market after being engaged to former MLB player Alex Rodriguez for two years.

It is not the first time that Lopez has canceled an engagement, though. We put together some of her most high-profile romances, divorces, and failed engagements. And yes, Ben Affleck and Jennifer Lopez’s relationship is included.

JENNIFER LOPEZ’S HUSBANDS

Everything started with Ojani Noa, a Cuban waiter that the singer met in Miami while filming “Blood and Wine.” The pair tied the knot in February 1997 but parted ways only 11 months later.

The drama didn’t stop with their divorce as Noa tried to sell a tape of their honeymoon in which she appeared “with a lack of clothing and in sexual situations.” Fortunately, J-Lo’s legal team prevented that from happening.

With Cris Judd, Lopez’s second husband, things were not as dramatic. They met in Spain in 2000 after he was hired to direct the music video of her song “Love Don’t Cost a Thing.”

They walked down the aisle in September 2001 but split in June 2002. For Judd, who said that their wedding was “a circus,” having his privacy breached was too much to handle.

With Marc Anthony, Jennifer Lopez had arguably the most stable relationship. They began dating in 2003 and tied the knot in June 2004 after he officially divorced former Miss Universe, Dayanara Torres.

The exes welcomed twins Max and Emme in 2008 but broke up in 2011. Rumors that Anthony had cheated on her were all over the internet, but he eventually cleared things up, saying that they split just because things stopped working. He added:

“People are trying to peg it on things because it was so shocking. It was like, it must have been something […] It wasn't something sensationalistic.”

JENNIFER LOPEZ’S BOYFRIENDS

Although Sean “Diddy” Combs and Lopez made up one of the power couples of the late 90s, their short relationship (1999-2001) was filled with infidelity allegations by Diddy.

Lopez would later reveal that while she didn’t regret their time together, she was “totally crying, crazy, and going nuts” with the rapper, adding that theirs was a tumultuous relationship that ended in “a bang.”

A happily-ever-after is no longer a possibility for [Lopez and Rodriguez].

Jennifer Lopez and backup dancer Casper Smart began dating in 2011, which immediately drew people’s attention as he is 18 years her junior. The pair broke up in 2014 amid rumors he was sexting with two transsexual models.

The following year, Smart and Lopez got back together, but they split for good in 2016. Smart thought he was ready for a relationship with a woman with children, but he wasn’t.

JENNIFER LOPEZ’S FIANCÉS

Ben Affleck and Lopez became one of the most overexposed celebrity couples of the 2000s, especially after the actor was seen cradling her derriere in “Jenny From the Block.”

The former couple met in 2001 on the set of “Gigli.” At the time, she was still married to Cris Judd. In November 2002, Affleck and J-Lo got engaged, but they called things off only two days before the ceremony.

Jennifer Lopez and Alex Rodriguez’s love story didn’t work, either. They began dating in March 2017 and got engaged in March 2019, but their relationship was filled with rumors and cheating allegations on his part.

On April 15, 2021, they revealed in a joint statement that they were better as friends. They plan to keep working together and supporting each other in their shared businesses and projects, but a happily-ever-after is no longer a possibility for them as a couple.