Jennifer Lopez’s Dating History: From Sean 'Diddy' Combs to Ben Affleck

Shortly after splitting with ex-fiancé Alex Rodriguez in April 2021, Jennifer Lopez reunited with former fiancé Ben Affleck, whom she married in July 2022

Jennifer Lopez’s love don’t cost a thing!

From A-list actors to big-time ballplayers, the globally renowned actress, singer and entertainer has famously romanced some of the world’s finest celebrity bachelors throughout her career. Still, only a handful of gents have been lucky enough to have J.Lo’s love for some time — and an even smaller few earned the privilege of her calling them her husband.

Get ready for a trip down memory lane: We’re revisiting the famous men "Jenny from the Block" has dated.

Sean “Diddy" Combs

Lopez and music mogul Sean “Diddy” Combs were hip-hop’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 told the publication in 2003. "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 two have since remained buddies, having cordially crossed paths in 2018 at Lopez’s All I Have Las Vegas residency show wrap party. When speaking to Vanity Fair in 2021, Combs also had nothing but kind words for his ex, whom he called "my friend."

Cris Judd

Backup dancer Cris Judd first connected with Lopez in 2000, when he was hired for her "Love Don't Cost a Thing" video. They tied the knot on Sept. 29, 2001, but had filed for divorce by July 2002 and finalized the dissolution of their marriage in January 2003. It was Lopez's second marriage after her 1997–1998 union with model-waiter Ojani Noa.

"Coming out of a torrid relationship, I meet this sweet person who's so refreshing," Lopez told Vibe in 2003 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."

Ben Affleck

The media sensation known as "Bennifer" was born on the set of Ben Affleck and Lopez's infamously bad movie Gigli (2003). The pair became engaged in November 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 officially broke up in January 2004.

"We didn't try to have a public relationship," Lopez told 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."

Shortly after calling it quits with ex-fiancé Alex Rodriguez in spring 2021, PEOPLE confirmed Lopez and Affleck were spending time together again, both in Montana and Los Angeles. "She is happy with him and enjoys spending time with him," a source told PEOPLE in May that year. By July, “Bennifer” was reborn as they made their romance Instagram official.

"I feel so lucky and happy and proud to be with him," Lopez said of reuniting with her former fiancé in February 2022. "It's a beautiful love story that we got a second chance." Two months later, the couple became engaged for the second time, with the pop star confirming her engagement via her On the JLo newsletter.

On July 16, 2022, Lopez and Affleck married in Las Vegas, with the couple’s children bearing witness to their nuptials. "It's a beautiful outcome that this has happened in this way at this time in our lives where we can really appreciate and celebrate each other and respect each other," she wrote in her newsletter at the time. "We always did, but we have even more of an appreciation because we know that life can take you in different directions."

The following month, the newlyweds celebrated their union again on Aug. 20, 2022, in a Georgia wedding ceremony surrounded by family and friends.

Marc Anthony

Lopez tied the knot with actor and singer-songwriter Marc 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 fraternal twins, daughter Emme Maribel and son Maximilian David.

The spouses announced their split in July 2011, 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 2014.

Despite ending their romantic relationship, Anthony and Lopez remain close friends and co-parents. “Marc and I are good how we are right now,” she told Watch What Happens Live with Andy Cohen of their friendship in 2017. “There’s a reason we’re not together. But we’re great friends, and we’re parents together. That has been even better for us. We met working, and that’s where we’re really magical. When we’re on stage together, and so we leave it there. That’s it.”

Casper Smart

Lopez began dating dancer and choreographer Casper Smart in October 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 split for good in August 2016. That October, a source told PEOPLE that Smart's infidelity is what prompted Lopez to call it quits. "She kicked him out because he cheated on her, and he got caught," the source said. "It happened two years ago, and he promised he would never do it again, and once he did, she was done."

Drake

The music stars first sparked relationship rumors in December 2016 with a cuddly photo on Instagram. They enjoyed several flirty date nights, and a source told PEOPLE that she and Drake seemed “really happy” together.

Although they appeared to enjoy each other’s company, an insider told PEOPLE in February 2017 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 told then-host Trevor Noah.

Alex Rodriguez

In March 2017, a source confirmed to PEOPLE that Lopez and the former MLB star had been “dating for a few weeks.” The insider added: "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 Los Angeles.

On March 9, 2019, Rodriguez proposed to her in the Bahamas, and the pair began planning a wedding, which was later derailed by the COVID-19 pandemic. But in April 2021, PEOPLE confirmed the stars had split.

"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 breakup. It's taken a while for them to even think about untangling it all."

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