Jennifer Lopez’s Dating History, Including Her 4 High-Profile Marriages and Failed Engagements

Ojani Noa

The singer, dancer and actress married the Cuban waiter in February 1997, but their marriage only lasted 11 months. In a 2022 interview with The Daily Mail, following Jennifer’s marriage to Ben, he said, “I wish her and Ben the best, but I’m not convinced it will last. Jen loves being in love but she’s been engaged six times. Ben is husband number four. I was husband number one and she told me I was the love of her life. When we lay in bed on our wedding night, she said we would be together for ever.” According to multiple reports, Ojani told the star he didn’t want the engagement ring back.

Sean ‘Diddy’ Combs

Shortly after their split, Jennifer found herself in an on-off relationship with the Grammy Award-winning rapper. The two met on the set of a music video, but their relationship came to an end for good in 2001. She would go on to reflect on their relationship during a 2003 interview with Vibe magazine. “It was the first time I was with someone who wasn’t faithful,” she told the publication, per Entertainment Weekly. “I was in this relationship with Puff where I was totally crying, crazy and going nuts, it really took my whole life in a tailspin … I never caught him, but I just knew. He’d say he was going to a club for a couple of hours and then never come back that night.”

Cris Judd

During her relationship with the former backup dancer, J.Lo discovered that love did, in fact, cost a thing. Cris, who met the superstar when he was hired to dance in her “Love Don’t Cost a Thing” music video, married Jennifer on September 29, 2001, but the two split by July 2002, and their divorce was finalized in January 2003. She previously told Vibe, per People, “Coming out of a torrid relationship, I meet this sweet person who’s so refreshing. But marriage is not just about love. I thought I had learned that in my first marriage … I loved Cris, still love him, he’s one of the best people. This wasn’t an easy thing to walk away from, but we didn’t have what it takes to make a marriage work.”

Ben Affleck (Round 1)

Before her divorce from Cris was finalized, Jennifer met Ben on the set of their failed film Gigli. However, one thing to come out of the box-office flop was “Bennifer,” the nickname that has stuck with the couple for over two decades.

After a whirlwind romance, Jen and Ben were engaged for the first time in November 2002, but they called off their wedding four days before the event due to the media obsession surrounding it and eventually split in January 2004.

Marc Anthony

After Bennifer ended the first time around, the “Let’s Get Loud” singer married Marc in June 2004, and they welcomed twins Max and Emme nearly two years later in February 2008. While many thought he was The One for the pop star, the couple split in July 2011. “I hung in there for seven years. I knew very quickly that it wasn’t the right thing,” she told W magazine in April 2016, per Us Weekly. “When my marriage ended, it was not easy to find forgiveness. It wasn’t the dream that I had hoped for, and it would have been easier to fan the flames of resentment, disappointment and anger. But Marc is the father of my children, and that’s never going away. So I have to work to make things right. And that is, by far, the hardest work I do.”

Beau ‘Casper’ Smart

Following her split from her third husband, Jennifer had an on-off relationship with her former backup dancer. While they split for good in 2016, Casper had nothing but good things to say about his ex when asked about her the following year. “Jennifer is, like, phenomenal, phenomenal, phenomenal,” he told Us Weekly in 2017.

Drake

Jennifer was first romantically linked to the rapper in December 2016, and shortly thereafter it was confirmed by multiple reports that they were officially dating. However, their relationship was extremely short-lived, and by March 2017, she said things were over. During an appearance on The Daily Show, she told then-host Trevor Noah, “Let me clear this up. I am not with Drake.”

Alex Rodriguez

Following Jennifer’s brief stint with Drake, she was quickly linked to the former New York Yankees player, and the couple announced their engagement in March 2019. It appeared that Jennifer had finally found The One, as the two continuously gushed over one another throughout the course of their relationship. However, trouble in paradise began in early 2021, and by April of that year, they had ended things. “We have realized we are better as friends and look forward to remaining so,” they wrote in part in a statement. It wasn’t long before photos of Jennifer with fourth husband Ben surfaced, and Bennifer was officially back on.

Ben Affleck (Round 2)

In 2021, Ben and Jen were photographed together multiple times, and it wasn’t long before they confirmed that Bennifer was back in action. They finally married in a surprise Las Vegas ceremony on July 16, 2022, and held a bigger celebration the following month. In May 2024, an In Touch source exclusively revealed that the two were headed for divorce.

Jennifer confirmed the split news by filing for divorce on August 20, 2024, the two-year anniversary of the couple’s Georgia wedding. In her divorce filing, she listed the date of separation as April 26, 2024. Before the “Get Right” singer filed her paperwork, the A-listers did not hide their marital issues and spent nearly the entire summer apart.