All the Famous Men Who've Dated Jennifer Lopez
Looking back at the star's high-profile romances over the years
SEAN "P. DIDDY" COMBS
Lopez and Combs were music's power couple from 1999 to 2001. The rapper was by her side for some of her most iconic red carpet moments, including the sultry green Versace dress she wore to the Grammys in 2000.
Lopez candidly discussed the relationship's challenges in Vibe magazine two years after the split. "It was the first time I was with someone who wasn't faithful," she revealed. "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."
The backup dancer first connected with Lopez in 2000 when he was hired for her "Love Don't Cost a Thing" video. They tied the knot in September 2001, but had filed for divorce by July 2002. It was Lopez's second marriage after her 1997 to 1998 union with model/waiter Ojani Noa.
"Coming out of a torrid relationship, I meet this sweet person who's so refreshing," Lopez later told Vibe about embarking on a whirlwind romance with Judd after ending things with Combs. "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."
The media sensation known as "Bennifer" was born on the set of Affleck and Lopez's infamously bad movie Gigli. The pair were engaged in 2002, the same year they documented the frenzy surrounding their relationship in Lopez's video for "Jenny from the Block." They called off the ceremony four days before they had planned to wed in 2003, citing "excessive media attention" as the reason behind the postponement. The couple had officially broken up by January 2004.
"We didn't try to have a public relationship," Lopez recounted to PEOPLE in March 2016. "We just happened to be together at the birth of the tabloids, and it was like 'Oh my God.' It was just a lot of pressure."
In May 2021, PEOPLE confirmed the pair were again spending time together, both in Montana and Los Angeles. "She is happy with him and enjoys spending time with him," a source told PEOPLE.
Lopez married Anthony in a private June 2004 ceremony, just months after ending things with Affleck. The surprise wedding came before the couple had even publicly acknowledged their relationship. In February 2008, the duo welcomed twins Emme and Maximilian.
The spouses announced their split three years later, writing in a joint statement to PEOPLE, "This was a very difficult decision. We have come to an amicable conclusion on all matters." The divorce was finalized in June of 2014. Despite ending their romantic relationship, Anthony and Lopez remain close friends and co-parents.
Lopez began dating the dancer and choreographer in 2011 after parting ways with Anthony. "I just got out of a big, heavy, devastating thing, and he's helped me heal," the singer told PEOPLE. "He's been there for me."
The couple was on-and-off during their time together but seemed to split for good in August 2016. A source told PEOPLE in October that Smart's infidelity prompted Lopez to make the break. "She kicked him out because he cheated on her and he got caught," said the source. "It happened two years ago, and he promised he would never do it again and once he did, she was done."
The music stars first sparked relationship rumors in December 2016, sharing a cuddly photo on Instagram. They enjoyed a number of flirty date nights and a source told PEOPLE that they "seem really happy." Although they seemed to enjoy one another's company, an insider revealed to PEOPLE in February that "it was never very serious." Lopez confirmed that whatever may have been brewing with the rapper was over in March 2017 when she appeared on The Daily Show. "Let me clear this up. I am not with Drake," she said.
In March 2017, a source confirmed to PEOPLE that Lopez and the former MLB star have been dating "for a few weeks." Added the source, "He has been around her family and she really likes that he is a dad." Soon, they were all over each other's Instagram feeds, sharing photos of their kids together in Miami and L.A.
"This has been a long time coming," a source told PEOPLE. "They are tied in their business worlds so it's not a cut and dry break up. It's taken a while for them to even think about untangling it all."