Jennifer Lopez’s Dating History: A Timeline of Her Famous Relationships, Exes and Flings

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Jennifer Lopez's Dating History: A Timeline of Her Famous Relationships, Exes and Flings

Love don’t cost a thing! Jennifer Lopez has famously been involved in several high-profile romances — and many of them didn’t result in a happily ever after. The Shades of Blue actress has been married three times and, in between, dated some of Hollywood’s biggest names, including Ben Affleck. The Second Act star kept it real about her quest to find everlasting love while speaking with Harper’s Bazaar in January 2019. “For me, the relationship journey has been very up and down. But it didn’t have to do with anybody else but me — it was about me figuring out me. Until you learn to love yourself, you can’t completely love [someone else] in a way that is pure and true. Once you do that, you can have relationships that are based on love and respect, that are supportive and nourishing,” Lopez said. “There’s an evolution there that had to happen for me. I feel like I’m in a better place now.” Lopez was previously married to Ojani Noa from 1997 to 1998, Cris Judd from 2001 to 2003 and Marc Anthony — with whom she shares twins Max and Emme — from 2004 to 2014. She was also engaged to Affleck from 2002 to 2004 and got engaged to Alex Rodriguez in 2019. Us Weekly confirmed in March 2021 that Lopez and Rodriguez were "working through some things" amid reports that they split and called off their two-year engagement. [jwplayer XMhH3iSs-zhNYySv2] Despite her history of divorce, the songstress revealed to Harper’s Bazaar in March 2018 that she had not given up on the possibility of finding forever love. “I do believe in marriage,” she said at the time. “And I would love to grow old with somebody in a committed relationship. But I’m not forcing anything right now.” She accepted Rodriguez’s proposal the following year. Lopez noted in January 2021 that part of her journey toward getting to know herself involved reflecting on her past romances. “I remember when I was going through therapy at the beginning, you know, kind of in my late 30s and there was a lot of talk about loving yourself and I was like, ‘I love myself,’” she recalled on Coach Conversations. “But obviously, I was doing all these things in, like, my personal relationships that didn’t seem like I was loving myself, but I didn’t even understand the concept of it. It took time and it’s a journey and it’s still a journey for me.” She and Rodriguez went on to confirm their split in April 2021 after months of speculation. She then rekindled a romance with Affleck and the singer announced their engagement — for the second time — nearly two decades after their initial split. Scroll through the photos below to relive Lopez’s dating history — from her marriages to her engagements and more!

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Ojani Noa

The Selena star married the producer in February 1997, but their marriage was short-lived; they divorced 11 months later. In August 2007, a court-appointed arbitrator issued a permanent injunction that forbid Noa from “criticizing, denigrating, casting in a negative light or otherwise disparaging” his ex-wife. Noa later appeared on Millionaire Matchmaker in 2016. 

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Sean 'Diddy' Combs

Lopez began dating the hip-hop mogul in 1999 after the pair met on the set of a music video, but they later split up in 2001. In a 2003 interview with Vibe magazine, the Maid in Manhattan actress claimed Diddy was unfaithful during their relationship. The former rapper, for his part, waxed poetic about Lopez in 2017, proclaiming she was “without a doubt” one of his great loves. The former couple remain friendly, embracing each other warmly backstage at her Las Vegas residency, All I Have, in September 2018.  

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Cris Judd

The Monster-in-Law actress met the dancer on the set of her "Love Don't Cost a Thing" music video and the two tied the knot in September 2001. The couple's marriage was over by June 2002 and their divorce was finalized in 2003. Judd explained that their marriage “just didn't work out” while speaking with Us Weekly in September 2014. “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. Everyone has baggage and problems. It's whether you want to deal with those problems,” he told Us at the time. “When you sign up to get married, you can't just walk away.” Judd has since remarried to Kelly Wolfe, with whom he shares daughter Vivienne.

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Ben Affleck

The Justice League star and Lopez — famously nicknamed “Bennifer” by the press — met while filming Gigli, and they got engaged in November 2002. The couple called off their wedding four days ahead of the event and later split up in January 2004. “I was eviscerated. I lost my sense of self, questioned if I belonged in this business, thought maybe I did suck at everything. My relationship [with Affleck] self-destructed in front of the entire world,” the “Not Your Mama” singer told Vanity Fair in December 2017 of the headlines surrounding the critically panned Gigli and her split from the Oscar winner. “It was a two-year thing for me until I picked myself up again.” In 2005, the Gone Girl actor later married Jennifer Garner, with whom he shares daughters Violet and Seraphina, and son Samuel. Affleck and Garner’s divorce was finalized in 2018.

In May 2021, Affleck and Lopez reunited and were spotted together on multiple occasions, including on a getaway in Montana and a romantic getaway to Miami. Us confirmed later that month that the couple were officially back together.  

"Jen and Ben are both very happy with each [other] and are excited to see where the relationship goes," a source exclusively revealed to Us. "They are full-on dating and very happy together."

In April 2022, Lopez announced that the couple were officially engaged for the second time. Us confirmed Affleck and the Parker actress wed in July 2022.

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Marc Anthony

Lopez and Anthony married in June 2004, welcoming twins Max and Emme in February 2008. However, they announced their split in July 2011. The Enough star later noted that she “knew very quickly that [their marriage] wasn’t the right thing,” telling W in April 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. 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."

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Beau 'Casper' Smart

Just four months after splitting from Anthony, the “Dinero” singer started dating the backup dancer in November 2011. Lopez later hired Smart as the creative director of her All I Have residency in Las Vegas. The former flames endured a bump in the road in 2014, when gossip site The Dirty claimed to have evidence that Smart had been exchanging photos and messages with a transgender model. They went their separate ways in June of that year but continued with their on-again, off-again relationship before splitting up for good in 2016. There weren’t any hard feelings following their final breakup, however. Smart told Us Weekly in March 2017, “Jennifer is, like, phenomenal, phenomenal, phenomenal.”

Credit: Courtesy of Jennifer Lopez/Instagram

Drake

The “God’s Plan” rapper and Lopez first connected backstage in December 2016 after he attended her All I Have show. In January 2017, a source revealed to Us Weekly the pair were dating and were “the real deal.” Drake pulled out all the stops while the pair dated, reportedly decking out an L.A. church for a makeshift winter wonderland-themed prom where they were “crowned” king and queen. However, in February of that year, Us confirmed that they had called it quits, with a source telling Us at the time that their brief relationship “died down a bit” after the “Nice for What” crooner embarked on his European tour. Drake touched on their romance in “Diplomatic Immunity,” rapping “2017 I lost a J. Lo / A Rotterdam trip had me on front page, though,” seemingly referring to the "Jenny From the Block" singer’s relationship with Alex Rodriguez. 

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Alex Rodriguez

Fourth time’s the charm? Lopez and the former Yankee announced their engagement in March 2019 after more than two years of dating. The pair — who were first linked in February 2017 — often gushed about their love and admiration for one another. In July 2018, the former Fly Girl penned a sweet tribute to her then-beau on his birthday: “Baby, spending time with you over the past year and a half … getting to know the real you more and more … I am surprised everyday by the generous, loving person you are to me and everyone around you.” 

In October 2018, a source told Us Weekly that the couple were looking into moving in together — which made sense since they had happily merged their families together (Rodriguez shares Natasha and Ella with ex-wife Cynthia Scurtis). In December 2018, Rodriguez noted that Lopez made him “feel like a kid again.” A source told Us that month, “An engagement is definitely on the horizon. Alex is obsessed with Jen and spends as much time as he can with her.” 

Lopez and Rodriguez postponed their wedding multiple times amid the coronavirus pandemic. Us confirmed in March 2021 that they were "working through some things" amid reports that the pair had split and called off their two-year engagement.

She and the retired athlete broke up the following month, writing in a joint statement to Today: “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."