The Most Tragic Moments Of Jennifer Lopez's Love Life

Jennifer Lopez has released countless songs about love and is the star of many feel-good rom-coms, but in real life, she has yet to have her happily ever after. With six engagements and four failed marriages, it’s safe to say that the “Ain’t It Funny” singer has been tragically unlucky in love. Before she rose to fame with the 1997 film “Selena,” Lopez had a short-lived marriage to producer Ojani Noa that only lasted 11 months. At the time, Noa was relatively unknown, and as Lopez rose to fame, the former “In Living Color” dancer began to have much more high-profile romances.

Sadly, Lopez’s latest heartbreak is from her rekindled relationship with Ben Affleck. After a very public end to their engagement in 2004, the two reunited 17 years later and finally tied the knot in 2022. Just when the world was rooting for Bennifer 2.0, there was talk that the couple was on the rocks. Sure enough, Lopez filed for divorce in August 2024, and it was the split we all saw coming. It seems the “Gigli” actor is done with love for now. “I’m not looking for anybody, because everything that I’ve done over the past 25, 30 years, being in these different challenging situations, what can I f***ing do when it’s just me flying on my own,” she stated to Interview. With Lopez’s string of breakups, it’s no wonder she’s not “Feelin’ So Good” about her tragic love life.

When Jennifer Lopez and Sean “Diddy” Combs started their messy relationship in 1999, the pop and hip-hop worlds came together. The “Waiting for Tonight” singer was already a rising star but being the Bad Boy exec’s girlfriend just catapulted Lopez to fame. Things took a disturbing turn when the two were partying at a New York City club and Diddy got into a physical altercation with another patron that turned into a shootout. The pair fled the scene and cops later found them in a car, where a gun was discovered under the seat. Lopez and Diddy were arrested but released shortly after, with no charges filed against Lopez. 

The gun incident wasn’t what caused Lopez to end things with Diddy; instead, her suspicions about his infidelity spurred their breakup in 2001. In an interview with Vibe (via Entertainment Weekly), she stated, “It was the first time I was with someone who wasn’t faithful. 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.” She added, “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.”

Jennifer Lopez and Ben Affleck were one of the biggest couples of the Y2K era, and although their first movie together, “Gigli,” was a flop, fans loved to stan their relationship. “Bennifer” was born, and you couldn’t see one without the other at any Hollywood event. Just months after they met, Affleck proposed to Lopez in 2002 with a giant pink bespoke Harry Winston diamond, and news outlets couldn’t get enough of them. So much so, that days before their wedding, they canceled their nuptials and stated, per People, “Due to the excessive media attention surrounding our wedding, we have decided to postpone the date.”

Unfortunately, the wedding never happened (this time) and Bennifer was no more in 2004. Years later in 2022, Lopez told Apple Music that following the split, she couldn’t even perform songs from her “This Is Me… Then” album, which was inspired by Affleck. “It was so painful after we broke up. Once we called off that wedding 20 years ago … it was the biggest heartbreak of my life. And I honestly felt like I was going to die,” she shared. At the time of the interview, Lopez had reunited with Affleck in hopes that they would be forever this time, but tragically, she had no way of knowing they would break up once again.

After Jennifer Lopez’s very public and painful breakup with Ben Affleck, she moved on with fellow singer Marc Anthony. It seemed like a match made in heaven — they were two artists in the same industry who had worked with each other previously. Their relationship didn’t have the fanfare that Bennifer did, and this time, Lopez made sure to keep things lowkey. She and Anthony married quietly in 2004, and four years later, they welcomed their twins Max and Emme. Lopez’s relationship with the “I Need to Know” singer was her longest to date but ultimately, Anthony filed for divorce in 2012.

The split was another heartbreak Lopez had to endure, and she later admitted to W in 2016, “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.” She also revealed that she knew early on that Anthony wasn’t the one. “I hung in there for seven years. I knew very quickly that it wasn’t the right thing,” Lopez stated.

In 2017, Jennifer Lopez decided to give love another chance — this time with MLB player Alex Rodriguez. The two got engaged in 2019 and were set for a 2020 wedding when COVID-19 derailed their plans. The “Love Don’t Cost a Thing” singer never ended up as Mrs. A-Rod, however, and the couple ended their engagement in 2021. Their split occurred after it came out during the “Southern Charm” Season 7 reunion that Madison LeCroy and Rodriguez (who was only identified as a married former baseball pro at the time) were allegedly FaceTiming each other, which the reality star claimed was the extent of their dalliance. The rumors may have been enough for Lopez to call off the wedding with Rodriguez. A source told The U.S. Sun, “These latest cheating rumors are the final straw. Everyone knows she can do better and doesn’t deserve this.”

LeCroy later opened up about her experience with Rodriguez on her castmates Craig Conover and Austen Kroll’s podcast, “Pillows and Beer.” At first, she didn’t believe that it was actually the retired baseball star DM’ing her, but Kroll recalled LeCroy later telling him, “This motherf***er’s FaceTimed me three or four times today.” The hairstylist chimed in, “I said, ‘If you’re looking for a side chick,’ which clearly he was, ‘it [isn’t] gonna be me.’ … I’m wifey material.”

Jennifer Lopez and Ben Affleck’s relationship looked promising the second time around, but things soon deteriorated after their marriage. Although the “Good Will Hunting” star joked on “Jimmy Kimmel Live” that he had a “very unhappy-looking resting face,” it seemed he was always miserable around Lopez. In a viral video shared on X, formerly Twitter, Affleck is seen walking ahead of his wife and opening her car door. The couple looks tense, and after Lopez is seated, Affleck slams the door, looking visibly frustrated.

In another instance, a bystander managed to capture photographs of Lopez and Affleck in their car, where they appeared to have a heated discussion, per the Daily Mail. “J.Lo looked a little bit sad. They were so deep in conversation that they didn’t even look to the side once. They only looked at each other and the traffic light,” the source shared. It seems that another reason for Affleck’s downtrodden visage is that he was actually miserable. “He was such a happy guy for all of 2023 but this year has been a completely different animal!” an insider told Radar. The source added, “Unfortunately, that makes him miserable to be around.”