Here’s Jennifer Lopez’s Complete Dating and Relationship History for Your Viewing Pleasure

POV: You and your roommates have popcorn and your favorite bottle of wine ready when you turn on Jennifer Lopez’s new rom-com, Office Romance. In the film, J.Lo plays airline CEO Jackie Cruz, who finds herself romantically entangled with the sexy new lawyer in the office (played by Brett Goldstein)…made all the more interesting by the fact that she and Brett reportedly had a real-life romance offscreen. Of course, this isn’t J.Lo’s first showmance, either, which is *exactly* why I’ve put my journalism degree to good use and found out everything there is to know about every guy Jennifer has dated (publicly, anyway).

From Marc Anthony to Drake to Ben Affleck (twice), here is J.Lo’s complete dating history for your viewing pleasure.

Jennifer's first public romance came around the same time as her Selena success. She met Ojani Noa while he was a waiter at a Cuban restaurant in Miami circa 1997. They were married for 11 months before they officially split in January 1998. Things between them remained friendly as J.Lo hired him to manage a Cuban restaurant she opened in L.A., but everything went south once she fired him six months later.

According to MTV, Ojani sued her for breach of contract; he was unsuccessful in the lawsuit, which resulted in a settlement that prohibited him from "publicly disparaging" or revealing information about J.Lo to make money. He didn't seem to care, as he started to shop around for a book that talked about his marriage with J.Lo (which she sued him for in 2006).

In 2009, Jennifer reportedly sent cease-and-desist letters to him for beginning production on a mockumentary titled How I Married Jennifer Lopez: The J.Lo and Ojani Noa Story. Per The Hollywood Reporter, the movie's producer tried to sue Jennifer for $10 million as she "interfered" with the production. The lawsuit was ultimately dismissed.

After all! Of! That! Ojani threatened to release intimate tapes from their honeymoon, but a judge banned them from seeing the light of day, per CBS News.

Remember the J.Lo and Diddy era? The couple would pull up to awards shows like the VMAs and the Grammys in the flashiest ensembles (including Jennifer's plunging green gown that invented the Google Image Search).

However! Jennifer reminisced on their 'ship in a 2003 interview with Vibe, dishing that it ended due to infidelity. "It was the first time I was with someone who wasn’t faithful," she said. "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."

After her relationship with Diddy ended, J.Lo met choreographer Cris Judd when he directed her "Love Don't Cost a Thing" music video. They wed in September 2001 and filed for divorce in July 2002. Of her connection with Cris, Jennifer told Vibe, "Coming out of a torrid relationship, I meet this sweet person who's so refreshing. But marriage is not just about love. I thought I had learned that in my first marriage." She continued, "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."

In a 2014 interview with Us Weekly, Cris said their relationship ended because he had trouble being connected to someone who was "high-profile." "You know, it's very tough. Your privacy is breached. You're no longer a normal person. [Our wedding] was a circus. I think several people got arrested trying to climb up a mountain … trying to sneak in. We actually rented the airspace."

Thus, Bennifer was born! The pair met on the set of their movie Gigli in 2001, and their chemistry translated offscreen as they became the Hollywood power couple in the early 2000s. Ben *famously* starred in J.Lo's music video for "Jenny from the Block," and in 2002, they got engaged.

Ben got Jennifer a $2.5 million 6-carat pink diamond engagement ring from Harry Winston (which inspired a whole Charli XCX song in 2020). Bennifer's wedding was postponed multiple times due to the major media frenzy surrounding it, and eventually never happened as their whirlwind romance came to an end in 2004. However, they remained friendly over the years (more on that later...).

After her "first big heartbreak" with Ben, Jennifer found love with Puerto Rican tropical salsa singer Marc Anthony. According to J.Lo's memoir, True Love, she and Marc first met in 1998 when he was in Paul Simon's Broadway musical The Capeman where he allegedly told her, "One day, you're going to be my wife."

The pair remained friendly over the years and collaborated on Spanish-language music together before they officially tied the knot in a secret ceremony in 2004. Jennifer revealed that Marc had been there for her following her breakup with Ben, telling Today in 2014, "To have one of my best friends, who I'd known for years, who I actually love and did have chemistry with, come into my life and say, 'I'm here'...What you need to know is, nobody can save you or heal you. Only you can do that for you."

In 2008, they welcomed twins Max and Emme together before separating in 2011. They have since remained good friends as they continue to collaborate on music and co-parent the twins.

After her split from Marc, J.Lo had an on-again-off-again relationship with her backup dancer, Casper Smart. At the time, an insider told People that it was "a fun fling" that was "not meant to turn into anything more."

Their relationship ultimately ended in 2016 because Casper had reportedly cheated on Jennifer. "She kicked him out because he cheated on her and he got caught," another source told People. "It happened two years ago, and he promised he would never do it again, and once he did, she was done."

Yep, you read that right. Drake and J.Lo had a short-lived fling in 2016, and it all started when he pulled up to cheer her on during her "All I Have" Las Vegas residency in December 2016. They then posted (now-deleted, womp) Insta posts of Jennifer lying across Drake’s lap and them cozying up to each other at a party. At the time, an anonymous source told E! News that she was "having fun" with the rapper. How! Ever! J.Lo dispelled the dating rumors during a 2017 interview on The Daily Show when she said, "Let me clear this up. I am not with Drake."

In 2018, Drake even name-dropped Jennifer on his track “Diplomatic Immunity,” rapping, “2010 was when I lost my halo / 2017 I lost a J.Lo.”

Now, let's get into when J.Lo met A-Rod. According to the "Can't Get Enough" singer, she originally met the athlete during a Yankees game in 2005. "We shook hands, and it was this weird electricity for, like, three seconds … Three to five seconds of looking at somebody right in their eyes, and getting stuck," she told Sports Illustrated in 2019. More than a decade later, the pair reconnected and started dating.

"I was having lunch somewhere and I saw him as he passed by. Afterwards, I went outside, and for some reason, I felt like tapping him on the shoulder," Jennifer said during a 2017 appearance on The Ellen DeGeneres Show. "He texted me, said, 'Let's go out to dinner,' and I said, 'Okay.' We had a nice dinner."

Since then, they officially started dating and got engaged in 2019. Their wedding faced delays due to the COVID-19 pandemic, and eventually, they called it quits in April 2021. The couple released a joint statement on The Today Show, saying, “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.”

For a while, Bennifer melted our cold, cold hearts after being back on! The pair rekindled their romance in 2021 when they were spotted hanging out after their respective splits from Alex Rodriguez and Jennifer Garner. In July 2022, they got married at a surprise ceremony in Las Vegas. Of course, they had a flashy, extravagant wedding the next month in Georgia.

At the end of 2022, Jennifer announced that she wrote a sequel to her 2002 album, This Is Me...Then, that was inspired by her revisiting her relationship with Ben. "When he came back into my life, again the same thing happened, where I felt so inspired and so overtaken with emotion that it was just pouring out of me," she told Zane Lowe in an interview for Apple Music. "When I feel good, I write music. And I wrote music, and I got in the studio in I think May, and by August when we got married, it was done."

Sadly, though, all we have left to remember the couple by is this ^^ because on August 20, after two years of marriage, J.Lo filed for divorce. An insider revealed to People at the time that the Atlas star "tried really hard to make things work, and is heartbroken. The kids are a top priority, as they always have been."

Office Romance started filming a few months after Jennifer’s divorce from Ben, and it wasn’t long before she sparked dating rumors with her co-star Brett. By May 2025, a DeuxMoi source claimed J.Lo and Brett were seen “canoodling in Cayo Levantado (in the Dominican Republic) at their Office Romance wrap party,” which was then followed by them sneaking “off to a private cabana to be alone.”

Hookup rumors continued swirling, with a source for the Daily Mail later alleging that “it was an open secret during filming about Brett and J-Lo—they got on like a house on fire from the start, and the chemistry was electric, which viewers will see. They were very touchy-feely and always laughing, and everyone suspected they were hooking up.”

However! After well over a year of dating (or, at least, hookup) rumors, another Daily Mail insider claimed that the relationship is “currently nothing more than a showmance for them over a romance.”

And finally, during a TODAY show appearance ahead of the Office Romance premiere, Savannah Guthrie grilled the co-stars about their relationship status but J.Lo finally confirmed they are “not dating.”

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Also: A source told Page Six that they were fully dating after the movie wrapped—only to break up pre-press tour.

Per the insider, “Once filming wrapped, they were free to take things further and dated for quite some time. They liked spending time together and Brett made her happy. But things just sort of fizzled out between them since last year.”

Luckily, it seems “there’s no bad blood but it just kind of came to a lull. They have a good friendship but in terms of romantic chemistry, that ship has sort of sailed. [They] dated for a bit and had a really strong physical attraction toward one another. Nothing major happened, they just felt like they were better off friends than anything else.”

If you say so!!