A closer look at Jennifer Lopez‘s dating history and timeline reveals the singer and actress has endured several heartbreaks over the years. From crushes to high-profile flings, canceled engagements, marriages, and divorces, Jennifer Lopez remains one of Hollywood’s hottest and most attractive female celebrities. As an A-list celebrity, Lopez’s relationships have been subject to public scrutiny for decades.
With breakup rumors swirling, Jennifer Lopez’s relationship has become one of the trendiest topics in 2024. Although the couple has not addressed the rumors publicly, it has left several speculations and counter-thoughts about what’s real and if it’s a big distraction. With fingers crossed on the fate of her latest two-year marriage, here’s a historical timeline of all of Jennifer Lopez’s relationships.
1984–1994: David Cruz
Jennifer Lopez found love early in life with David Cruz. He was her high school sweetheart, and he had begun dating before the fame and riches. Their love was pure and untainted. They were teenagers with dreams of winning together. Cruz reportedly moved to Los Angeles to be with Lopez and was entirely committed to her success. Jennifer Lopez and David Cruz reportedly dated for about a decade before splitting in 1994, before she got her breakthrough role in Selena (1997). Jennifer Lopez described their love, stating, “You get lucky; you have a first love like that.” Sadly, David Cruz died from heart disease in March 2020 at age 51.
1997–1998: Ojani Noa
Ojani Noa is one love affair Jennifer Lopez never forgot in a hurry, and all for the wrong reasons. Lopez met Ojani Noa at a Cuban restaurant in Miami, where he worked as a waitress. Although it was around the same time she found success with Selena, Lopez wasn’t yet a full-blown celebrity. The couple were soon engaged and married on February 22, 1997. Ojani Noa became Jennifer Lopez’s first husband. However, the marriage ended almost as quickly as it happened. By early 1998 the couple were divorced.
Although they reportedly remained friends initially, things went south quickly after a few months. By 1998, Jennifer Lopez had become a famous face and name. Jennifer Lopez spent the next decade in court trying to stop Noa from disparaging comments or revealing personal/intimate details about their time together. Hellbent on making money, Ojani Noa reportedly sought book deals and wanted to produce a mockumentary. Cease-and-desist letters were sent to Noa and the producers in 2009 to halt and stop production. Lopez’s marriage to Ojani Noa may have been her shortest, but the sour taste left behind lasted for years.
1999–2001: Sean “P. Diddy” Combs
Sean Combs, known as P. Diddy back then, was Jennifer Lopez’s first high-profile relationship. By 1999, Jennifer was a star, with her debut album launch and all the success that came with it. With P. Diddy’s success as a music and business mogul, the couple quickly became one of Hollywood’s power couples. However, it was practically an on-again, off-again relationship from 1999 until they finally split in 2001. Being a high-profile relationship, it brought more attention to Jennifer Lopez’s personal life.
Even Lopez admitted at some point that the relationship “was always something I knew would end.” Several months into the relationship, on December 27, 1999, the couple were at a Times Square nightclub when a shootout occurred. Jennifer Lopez and Sean Combs were arrested and charged with criminal possession of a weapon and possession of stolen property. Although Lopez’s charges were dropped within an hour, Combs was charged to court. He was finally acquitted of all charges in March 2001, the same year the couple split.
2001–2003: Cris Judd
Jennifer Lopez began dating her former backup dancer, Cris Judd. It may not have been a high-profile relationship, but it was a safe space for Lopez to take control of her privacy and personal life. The couple met while shooting Lopez’s “Love Don’t Cost a Thing” music video, with Judd as a backup dancer. Judd may not have a net worth nearly close to a quarter as Sean Combs, but luckily, Jennifer Lopez’s love “doesn’t cost a thing.” Unsurprisingly, the couple married on September 29, 2001. However, the 2000s wasn’t like the 1990s. As one of the biggest superstars in the world, Lopez’s wish for privacy was only a pipe dream.
The couple split on January 26, 2003, with Lopez finally learning that although “love don’t cost a thing,” it takes more than love to keep it going. She stated, “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.” She continued, “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.”
2002–2004: Ben Affleck
Judging by the timeline from when they met and began dating, Jennifer Lopez and Ben Affleck began dating before her divorce from Cris Judd was finalized. Although they hadn’t worked together at the time, as actors and celebrities, Affleck and Jennifer Lopez’s paths crossed in the past. However, they met officially when they began filming Martin Brest’s romantic crime comedy Gigli. Lopez and Affleck led the movie’s cast, playing each other’s love interest. They took the romance from the screen to the real world, birthing the term “Bennifer” to describe their love affair.
The couple were reportedly so in love that Affleck appeared in one of Lopez’s popular music videos, “Jenny from the Block.” However, he wasn’t a backup dancer; he was the main love interest in the video. Lopez’s third studio album, This Is Me… Then, was also reportedly dedicated to and inspired by Ben Affleck. The couple were engaged by November 2002 while waiting for divorce from Cris Judd to be finalized. Although the wedding was initially fixed for September 14, 2003, the excessive media coverage forced them to postpone it.
At the time, they were Hollywood’s most iconic couple, and like vultures to rotten meat, the paparazzi lived and breathed everything about Bennifer. Although he was no stranger to fame, Affleck was no longer comfortable with the entire media frenzy and attraction Bennifer was bringing to his seemingly “quiet” life. The couple officially ended the engagement sometime in January 2004. According to Jennifer Lopez, it was her “first real heartbreak.”
2004–2014: Marc Anthony
Jennifer Lopez walked away from the Bennifer frenzy, realizing she had to intentionally keep her personal life private. She found love again in fellow singer Marc Anthony. The couple married on June 5, 2004, and Lopez was ready to be a mother. On February 22, 2008, Jennifer Lopez and Marc Anthony gave birth to twins Emme Muñiz and Max Muñiz. Marc Anthony has been Jennifer Lopez’s longest husband and marriage. The couple stayed together for a decade, finalizing their divorce on June 16, 2014.
2011–2016: Casper Smart
A true hopeless romantic at heart, Jennifer Lopez gave love a chance again with professional dancer Casper Smart. They met during one of Lopez’s music video shoots and clicked. Although it had begun as a fling, with Lopez being older by 18 years, they continued to see each other consistently for about a year. After that, it became an on-again, off-again relationship until it ended in 2016. Casper Smart later admitted, “I was very young and selfish. I thought I was ready for a relationship with a woman with kids and everything.”
2016–2017: Drake
Jennifer Lopez has had several flings in her life but none was heavily publicized like that with Canadian rapper and singer Drake. It was also the first major fling Lopez openly denied. Whatever happened between them, fling or not, Lopez wasn’t ready to add Drake to her growing list of lovers. Lopez categorically stated in a 2017 The Daily Show interview, “Let me clear this up. I am not with Drake.” However, in 2018, Drake, in his “Diplomatic Immunity” song, dropped a line that said, “2010 was when I lost my halo / 2017 I lost a J.Lo.”
2017–2021: Alex Rodriguez
Jennifer Lopez’s next high-profile relationship was with then-New York Yankees baseball player Alex Rodriguez. Although they had met earlier briefly, they began dating in February 2017. The couple seemed madly in love, with Rodriguez proposing in March 2019. Although plans were underway for a wedding, the COVID-19 pandemic caused delays, with the wedding postponed twice. Afterward, rumors began swirling about a breakup.
Jennifer Lopez and Alex Rodriguez issued a joint statement to The Today Show, stating, “We have realized we are better as friends and look forward to remaining so. We will continue to work together and support each other on our shared businesses and projects. We wish the best for each other and one another’s children. Out of respect for them, the only other comment we have to say is thank you to everyone who has sent kind words and support.”
2021: Ben Affleck
Reports of a possible comeback of Bennifer were first reported in April 2021. It wasn’t until July that Lopez publicly confirmed and acknowledged it. Although he had proposed the last time, Ben Affleck walked away, leaving Lopez heartbroken. Interestingly, 20 years after his proposal to Jennifer Lopez, Affleck proposed again in April 2022. The couple married on July 16, 2022, in a private ceremony in Las Vegas. The couple have been together until recent rumors of a split emerged in 2024. If you enjoyed reading about Jennifer Lopez’s dating history, read about Kristen Stewart’s relationship history.
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