Jennifer Lopez is a relationship girl, there's no doubt about it.
Ever since she broke into the scene in the 1990s, J.Lo has kept a man by her side. Regardless of the many jokes made about her relationships, Lopez carries the title of hopeless romantic with pride. And despite many failed attempts at love, she has continued to give love a chance, even if it ends in heartbreak or divorce.
People often make jokes about how many times she has said “yes” to a proposal or how many “I dos” she has said at the altar, but none of it matters now that she has seemingly found her happily ever after. While she seemed head over heels in love with every guy she has been with, Lopez’s one true love has always been Ben Affleck. The power couple began dating in the early 2000s, and after a movie flop and some drama, they called off their engagement, leaving Bennifer fans and Lopez heartbroken.
Years later, 17 to be exact, the couple reunited, birthing Bennifer 2.0. They both went on to marry other people during their time apart and had children from previous relationships, but they finally made it to the altar in 2022. Now in her 50s, Lopez seems to have found the love she was seeking. In her upcoming cinematic experience This Is Me…Now, she explores her long dating history and zeros in on a lack of self-love as the culprit behind her failed relationships. During that journey of finding herself, she goes through the ups and downs of love, but in the end, after some healing, she reconnects with the one man who has always been in the back of her mind.
Ahead of her new album and film This Is Me…Now, we have gone down memory lane to relive all of J.Lo’s relationships and flings, which all led her back to Ben.
David Cruz
When: 1984–94
David Cruz was reportedly Lopez’s high school sweetheart. Their relationship began when they were just teenagers, and they stayed together through the mid-’90s but called it quits before she landed her breakthrough role in Selena. “You get lucky, you have a first love like that,” J.Lo later said about Cruz.
“They were high school sweethearts,” a source told People about the couple. “He was soft-spoken and kind and he would do anything for Jennifer. You could see her trajectory early on and at the time he didn’t mind seeing her take the lead. He was completely content with that. He just loved her.” Cruz passed away in 2020.
Ojani Noa
When: 1997–98
No other ex has publicly stressed J.Lo out more than Ojani Noa. She married the Cuban waiter in February 1997, but their marriage only lasted 11 months. They divorced in January 1998 but Noa continuously spoke about his time with his ex for years to come. The former couple have been involved in legal disputes that have ended up in court, and Noa was prevented from publishing a tell-all book about their relationship and from using private honeymoon footage of Lopez in a documentary. A court-appointed arbitrator forbid Noa from “criticizing, denigrating, casting in a negative light or otherwise disparaging” his ex wife in In August 2007.
Tommy Mottola
When: 1998
While this romance was never confirmed, it was rumored that Sony Music executive Tommy Mottola briefly dated Lopez after his divorce from Mariah Carey in 1998, which was in the same year she divorced Noa. Mottola attended the 1998 Grammy Awards alongside Lopez, and soon after, it was announced that Lopez had signed a record deal with Sony. This was said to be the start of Carey and Lopez’s rumored feud. Mottola is 21 years older than Lopez.
Diddy
When: 1999–2001
Lopez was in an on again–off again, highly publicized relationship with Diddy from 1999 to early 2001. They became a power couple as she kicked off her singing career. In December 1999, Lopez and Combs were arrested and charged with criminal possession of a weapon after the now-infamous shooting at a NYC nightclub. Lopez’s charges were quickly dropped, but Combs was acquitted of all charges at trial in early 2001. They broke up shortly thereafter, and she later told Vibe magazine that the music producer had been unfaithful. The pair remained friendly after their split.
Cris Judd
When: 2001–03
Lopez met Cris Judd on the set of her music video for “Love Don’t Cost a Thing.” Judd was a background dancer in the video, which was released in 2001, and they were married in September of that year. They called it quits by June 2002, and their divorce was finalized in 2003. “I can't give you the answer as to why her relationships don't work. I think that it's that it is work. It's whether you want to work on it or not,” Judd told Us Weekly in September 2014. “Everyone has baggage and problems. It's whether you want to deal with those problems.” He added: “When you sign up to get married, you can't just walk away.”
Ben Affleck
When: 2002–04
Lopez began her relationship with Ben Affleck before her divorce with Judd was finalized. The couple’s relationship began on the set of their movie Gigli in December 2001. Their relationship was heavily publicized, and they were given the moniker “Bennifer,” and became one of Hollywood’s most famous couples. Affleck proposed in November 2002, but their wedding, which was scheduled to take place on Sept. 14, 2003, was postponed just days before due to "excessive media attention."
Their film was released in August 2003, but it tanked at the box office and with critics, which reportedly also caused a strain in their relationship along with all the media scrutiny. They called off their engagement in January 2004. Lopez has been open about Affleck being her one true love and biggest heartbreak.
Marc Anthony
When: 2004–14
Outside of her relationship with her high school sweetheart, Lopez’s longest relationship so far has been with salsa singer Marc Anthony. The pair collaborated on a song called “No Me Ames” in the ‘90s, and remained close. Lopez surprised everyone when she married the singer just five months after her split from Affleck. The pair welcomed twins Emme and Max in 2008. After years of collaborating on music, tours, and movies, the couple announced that they were separating in 2011. The singer filed for divorce in 2012, and it was finalized in June 2014. The former couple has also remained friendly after their split, but she said she knew early on that they weren’t going to work out.
"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,” Lopez told W magazine. “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."
Casper Smart
When: 2011–16
Casper Smart met Lopez when on the set for her “Dance Again” music video. They dated on and off from November 2011, before calling it quits in 2016. The couple went through some drama, with reports of him texting other people. “I was single; she was single. It started out as flirting, then became more than flirting. There was a connection,” he said on Univision’s morning show Despierta América.
“Neither of us thought it would be more than a fun time, and suddenly we were spending time together. We enjoyed each other’s company; there was chemistry.” He added: “I was very young. I was 23 or 24. She was 18 years older, so she was about 42 years old with two kids. But in the moment, everything just clicked. We spent every day together for a year.”
Ultimately, the dancer said their age difference was what got in the way, saying: “I was very young and selfish. I thought I was ready for a relationship with a woman with kids and everything.”
When: 2016-17
Did they or didn't they? Things seemed to quickly heat up between Drake and Lopez after he attended her her All I Have residency in Las Vegas in December 2016. A month later, Us Weekly reported that the pair were dating, with a source saying that they were “the real deal.” They didn't last long, and after going Instagram official with a few photos and being spotted out to dinner together, their fling died down in February 2017. After she began a relationship with Alex Rodriguez soon after, Drake mentioned Lopez in “Diplomatic Immunity,” saying: “2017 I lost a J. Lo / A Rotterdam trip had me on front page, though."
Alex Rodriguez
When: 2017-2021
Alex Rodriguez and Lopez's dating rumors began to circulate in February 2017. The couple were open about their relationship from the start and often gushed about their love. Things progressed quickly between them, and soon they were living together and becoming a blended family with their respective children. The former baseball star proposed in March 2019 after more than two years of dating.
Due to the pandemic, the couple postponed their wedding several times, and in 2021 rumors began swirling that there was trouble in paradise and that they had split. Later that year, they announced they were calling off their engagement. “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," the shared in a statement to Today in April 2021. "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."
Ben Affleck, again
When: April 2021—Present
Soon after announcing her split from Alex Rodriguez, it was reported that Lopez and Affleck were dating again. The pair was spotted together in Miami in May 2021, and a source told TMZ that they had been emailing each other since early February while she was in the Dominican Republic filming Shotgun Wedding,. She publicly confirmied they were back together that July. Then, in April 2022, a year after they reconnected and 20 years after the first proposal, Lopez announced their were engaged again. The couple eloped and tied the knot in Las Vegas on July 16, 2022, with their kids in tow, and held a wedding celebration for family and friends the following month in Georgia. The couple have made various public appearances together on red carpets, award shows and movie premieres since, proving that Bennifer is perhaps here to stay this time around.
