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

Mar. 15, 2025

Sean “Diddy” Combs and Jennifer Lopez; Ben Affleck and Jennifer Lopez.Photo:KMazur/WireImage; Steve Granitz/FilmMagic

KMazur/WireImage; Steve Granitz/FilmMagic

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 most famous celebrity bachelors, includingAlex Rodriguez.Still, only a handful of gents have been lucky enough to experience J.Lo’s love — and an even smaller few earned the privilege of calling her their wife.Most recently, Lopez was married to her longtime loveBen Affleckfor two years before shefiled for divorcein August 2024. The actress' longest marriage was withMarc Anthonyfrom 2004 to 2014. During that time, they welcomed twinsMax and Emme.Get ready for a trip down memory lane: We’re revisiting the famous men “Jenny from the Block” has dated.

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 most famous celebrity bachelors, includingAlex Rodriguez.

Still, only a handful of gents have been lucky enough to experience J.Lo’s love — and an even smaller few earned the privilege of calling her their wife.

Most recently, Lopez was married to her longtime loveBen Affleckfor two years before shefiled for divorcein August 2024. The actress' longest marriage was withMarc Anthonyfrom 2004 to 2014. During that time, they welcomed twinsMax and Emme.

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

01of 07

Sean “Diddy” Combs

Jennifer Lopez and Sean Combs.George De Sota/Newsmakers/Getty

Lopez candidly discussed the relationship’s challenges inVibemagazine two years after the split. “It was the first time I was with someone who wasn’t faithful,“she told the publicationin 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 cordiallycrossed paths in 2018at Lopez’sAll I Have Las Vegasresidency show wrap party. Whenspeaking toVanity Fairin 2021, Combs also had nothing but kind words for his ex, whom he called “my friend.”

02of 07

Cris Judd

Jennifer Lopez and Cris Judd at the 74th Annual Academy Awards in 2002.KMazur/WireImage

“Coming out of a torrid relationship, I meet this sweet person who’s so refreshing,” Lopez toldVibein 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.”

03of 07

Ben Affleck

Jennifer Lopez and Ben Affleck at the 2003 Los Angeles premiere of ‘Gigli’.Jeff Kravitz/FilmMagic

The media sensation known as “Bennifer” was born on the set ofBen Affleckand Lopez’s infamously bad movieGigli(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.” Theycalled off the ceremonyfour 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-fiancéAlex Rodriguezin spring 2021, PEOPLE confirmed Lopez and Affleck were spending time together again, both in Montana and Los Angeles. “She is happy with himand enjoys spending time with him,” a source told PEOPLE in May that year. By July, “Bennifer” was reborn as they made their romanceInstagram 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 couplebecame engaged for the second time, with the pop star confirming her engagement via her On the JLo newsletter.

On July 16, 2022, Lopez and Affleckmarried 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.”

Lopez eventuallyfiled for divorceon Aug. 20, 2024, after months of marriage turmoil andliving separatelyfrom Affleck.

“She tried really hard to make things work, and is heartbroken,” a source told PEOPLE.

04of 07Marc AnthonyMarc Anthony and Jennifer Lopez.GettyLopeztied the knotwith actor and singer-songwriterMarc Anthonyin 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 duowelcomed fraternal twins,daughter Emme Maribel and son Maximilian David.The spousesannounced their splitin 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 toldWatch What Happens Livewith Andy Cohenof 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.”

04of 07

Marc Anthony

Marc Anthony and Jennifer Lopez.Getty

Lopeztied the knotwith actor and singer-songwriterMarc Anthonyin 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 duowelcomed fraternal twins,daughter Emme Maribel and son Maximilian David.

The spousesannounced their splitin 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 toldWatch What Happens Livewith Andy Cohenof 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.”

05of 07Casper SmartCasper Smart and Jennifer Lopez at the 73rd Annual Golden Globe Awards in 2015.Steve Granitz/WireImageLopez 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 couplewas on and offduring their time together butsplit for goodin August 2016. That October, a source told PEOPLE that Smart’s infidelity is what prompted Lopez to call it quits. “She kicked him outbecause 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.”

05of 07

Casper Smart

Casper Smart and Jennifer Lopez at the 73rd Annual Golden Globe Awards in 2015.Steve Granitz/WireImage

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 couplewas on and offduring their time together butsplit for goodin August 2016. That October, a source told PEOPLE that Smart’s infidelity is what prompted Lopez to call it quits. “She kicked him outbecause 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.”

06of 07DrakeDrake and Jennifer Lopez.Source: Drake InstagramThe 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 andDrakeseemed “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 onThe Daily Show. “Let me clear this up. I am not with Drake,” she told then-hostTrevor Noah.

06of 07

Drake

Drake and Jennifer Lopez.Source: Drake Instagram

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 andDrakeseemed “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 onThe Daily Show. “Let me clear this up. I am not with Drake,” she told then-hostTrevor Noah.

07of 07

Alex Rodriguez

Alex Rodriguez and Jennifer Lopez.Karwai Tang/WireImage

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.

“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.”

source: people.com