Spoiler: She’s had five weddings.
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Jennifer Lopez‘s relationship history is pretty legendary, and she’s not shying away from it in her new Amazon Prime documentary, The Greatest Love Story Never Told. She’s spilling the tea once and for all, and luckily for viewers, her kettle is full.
The documentary, released on February 27, is a behind-the-scenes peek into the making of Jennifer’s newest film, This Is Me…Now: A Love Story, which details the star’s marriages, relationships, and eventual journey back to loving herself.
“I’ve decided to share my story that I’ve never shared with anyone in the world,” she shares in the trailer to the documentary. “I’ve been married four times now…I’m sure people watching from the outside were like ‘What is this girl’s problem?’”
Yep, Jennifer tied the knot four times and was engaged twice before settling down with her Boston Prince Charming, Ben Affleck. (Don’t worry: Ben and Jen are apparently written in the stars, with intuitive astrologer Rachel Lang telling Women’s Health that their dual Leo signs mean they’re “loyal to the core.”)
In a 2019 interview with Harper’s Bazaar, J.Lo got candid about her dating history. “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,” she said. “Until you learn to love yourself, you can’t completely love [someone else] in a way that is pure and true.”
In the trailer for the doc, Jennifer shared she was always afraid of being alone.
Here’s a look back at J.Lo’s relationships—from Ben to a certain “Passionfruit” rapper to Ben…again.
Alex Rodriguez
J-Rod not only seemed like the ultimate power couple—but each other’s biggest cheerleaders. The pair dated for four years beginning in 2017. On March 10, 2019, they announced their engagement on Instagram. The couple planned to get married during the summer of 2020—but they pushed back their wedding date twice due to COVID-19 before calling the whole thing off.
There were also rumors that Alex had cheated on Jennifer with Southern Charm star Madison LeCroy, but it’s unclear if that had anything to do with the breakup.
J-Lo and A-Rod released a joint statement to TODAY about their separation. “We have realized we are better as friends and look forward to remaining so,” the statement read. “We will continue to work together and support each other on our shared businesses and projects.” And that they “wish the best for each other and one another’s children.”
When things went south, A-Rod definitely didn’t handle the breakup well. He posted several mopey (now-deleted) Instagram posts that relayed how broken he was without J.Lo, including a video of a shrine to her on his Instagram story in 2021, per Harper’s Bazaar.
A source later told Entertainment Tonight that J.Lo has moved on. “Jen is focused on herself and doesn’t even think twice about A-Rod or his current love life,” the source said. “She wishes [Alex] the best, but it’s not something that bothers her or takes up space in her mind whatsoever. She just wants everyone to be happy, whatever that might entail.”
They also added this kicker: “A-Rod is 100 percent at the back of her mind, and his dating life doesn’t faze her.”
In the documentary, J.Lo shares how this (extremely) public breakup impacted her and how she had to up her self-love in the aftermath of the betrayal and heartbreak.
Drake
In late 2016, J.Lo was rumored to be dating the “In My Feelings” hitmaker. She denied the rumors on Ellen in February 2017, saying the duo just worked on a song together and that the photos published on Instagram just showed them “hanging out.”
On the contrary, Drake seemingly hinted at their relationship in his song “Diplomatic Immunity.” “2017 I lost a J. Lo / A Rotterdam trip had me on front page, though,” he rapped. Sounds like a solid J. Lo and A. Rod reference to me, but hey, you never know.
Casper Smart
Jennifer dated Casper Smart for two and a half years. At the time, J.Lo was 42, while Smart was 24. They met while he worked as a backup dancer for the “On The Floor” singer.
“It was really professional for a very long time before anything even happened,” Smart said in 2012, per Page Six. “It just really spontaneously happened, I guess. The chemistry was there. You can’t fight it.”
They split in 2014 amid reports that Smart had been allegedly sexting with two models, per Page Six. They briefly rekindled their romance in 2015 before breaking things off for good in 2016.
Marc Anthony
J.Lo started dating Marc Anthony in 2003, shortly after she broke off her first engagement with Ben Affleck. The couple got married in 2004, and was together for seven years, until the couple split in 2011.
They have two children together, twins Maximilian and Emme, 15. While it ultimately didn’t work out, J.Lo told Sunday TODAY that Marc was always supportive of her career.
“While I was married to Marc, he really helped me with my confidence, and he saw where I suffered,” she said, adding that Marc often told her she was “a great singer” and encouraged her not to let anyone make her think otherwise.
In the documentary, J. Lo shares that one of her ex-husband’s friends, Anthony Ramos, turned down an offer to appear in This Is Me Now…:A Love Story because of his friendship with Marc Anthony.
Ben Affleck
The doc definitely features a lot of Ben and Jen’s love story. She even shares that she drew inspiration from her “bible.” This is what she calls a book Ben gave her on the first Christmas back together.
“It is every letter and every email that we wrote to each other from 20 years ago to today,” she told the crew in the doc. Ben even titled it, “The Greatest Love Story Never Told by Jennifer Lopez and Ben Affleck 2001 to 2021… and Counting.”
As a reminder, J.Lo and actor Ben Affleck hit it off on the set of Gigli in 2002, and the pair became engaged less than a year later. The couple, affectionately called “Bennifer,” called off the wedding in 2003.
Still, Ben told The Hollywood Reporter in 2012 that they kept in touch. “We don’t have the kind of relationship where she relies on me for advice,” he said. “But we do have the kind of relationship where there’ll be an e-mail saying, ‘Oh, your movie looks great.’ I remember when she got American Idol. I said: ‘This was really smart. Good luck.'”
Jennifer told Today in 2014 that Ben was her “first big heartbreak.” She also shared that her future husband Marc Anthony was there to support her in the aftermath. “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,” she said.
In 2020, Ben notably told the New York Times that J.Lo should’ve gotten Oscar recognition for her performance in Hustlers. “I keep in touch periodically with her and have a lot of respect for her,” he said, per US Weekly. “How awesome is it that she had her biggest hit movie at 50? That’s f–king baller.”
Then, in April 2021, J.Lo and Ben were spotted in an SUV together, and the rumors started flying that they rekindled their romance. They were photographed together constantly throughout the summer of 2021. In April 2022, Jennifer formally announced their engagement in her newsletter, On The J.Lo.
“We’re older now, we’re smarter, we have more experience, we’re at different places in our lives, we have kids now, and we have to be very conscious of those things,” Jennifer told People. “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.”
And on July 17, 2022, Jennifer confirmed via her newsletter, On The J. Lo, that she had married Ben in a private ceremony in Las Vegas. Bennifer stood in line for a marriage license with four other couples. She wore a dress from an old movie and they kept things simple.
“We read our own vows in the little chapel and gave one another the rings we’ll wear for the rest of our lives,” she wrote in her newsletter, adding, “in the end it was the best possible wedding we could have imagined…at very, very long last.”
The newlyweds kept the festivities going with a romantic Paris getaway and a big shindig at Ben’s big property in Georgia. Jen and Ben brought their friends and fam together for a Friday night rehearsal dinner, a Saturday ceremony, and a barbecue and picnic on Sunday. J. Lo wore a custom Ralph Lauren dress made in Italy, Page Six reported.
Now, the pair is back to being everyone’s favorite celebrity couple.
J.Lo recently opened up to Variety about life with Ben, noting that the couple has talked about working together again. “We love being together and working together so, yeah, you never know,” she said.
In the documentary, Ben shared that he had reservations about opening up their love story to the world.
“I don’t really love being in the making of a documentary about my personal life, which is why I’m so relieved that I’m not really, it seems like I might be in this, but I’m not really,” he shared in the doc. “I was worrying for no reason. The movie wasn’t about me. It was about the ability to love yourself, and that love story is a lot f******* harder to find than Prince Charming.”
While Ben likes to keep his life a little closer to the vest, he has had to adapt to Jennifer’s loud way of loving him and expressing herself.
“I certainly do the same things, but things that are private, I have always felt, are sacred and special because, in part, they’re private,” Ben says. “So this was something of an adjustment for me.”
Even Jane Fonda tried to talk J. Lo out of opening up about her love life for the cameras. The two starred in the movie Monster-in-Law together, and Jennifer says Jane has always been protective of her.
“I want you to know that I don’t entirely know why, but I feel invested in you and Ben, and I really, really, really want this to work,” Jane tells her over the phone in the doc, per TODAY. “However, this is my concern. Like, it feels too much like you’re trying to prove something instead of just living it. You know, every other photograph is the two of you kissing and the two of you hugging.”
Jennifer tells Jane that it’s authentic, and they’re not trying to prove something, but it’s sweet to see this protective moment between the women.
Cris Judd
J.Lo’s second husband was dancer and choreographer Cris Judd, to whom she was married for just nine months from 2001 to 2002. They met on the set of her music video, “Love Don’t Cost a Thing,” which Judd directed.
It was love at first sight… for him, at least. “So, when Jennifer walks in, I shake her hand and we kinda look at each other—and in my head, I’m like, ‘Oh my God, I’m going to marry this woman,'” Judd told Oprah on an episode of “Where Are They Now?” Ultimately, Judd couldn’t handle the fame.
“Your privacy is breached. You’re no longer a normal person,” he told US Weekly in 2014. “Unfortunately, it just didn’t work out.”
J.Lo later told Vibe that she has nothing but good things to say about her ex. “I loved Cris, still love him, he’s one of the best people,” she said. “This wasn’t an easy thing to walk away from, but we didn’t have what it takes to make a marriage work…. Cris knows the last thing I ever wanted in this f—— world was to hurt him.”
Cris is also a Leo, like Ben and A-Rod. J.Lo seems to have a type!
Sean ‘P. Diddy’ Combs
Could this couple be any more ’90s? Jenny from the Block dated fellow music artist Puffy Daddy/Sean John Combs (now known as Diddy) from 1999 to 2001. They began dating around the release of J.Lo’s debut album On The 6 and–get this—once got arrested together.
Unfortunately, this relationship was reportedly turbulent and full of infidelity, which eventually led to the couple’s breakup.
“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,” J.Lo told Vibe in 2003. “I never caught him [cheating], 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.” Ouch.
J.Lo shared that she and Diddy broke up so often that he didn’t believe it when she ended things for good in February 2001. “I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?” she said.
Like Drake, Diddy is a Scorpio, which isn’t the most compatible sign with J.Lo’s Leo. But, they do share a sense of loyalty, according to celeb astrologer Aliza Kelly.
Ojani Noa
J.Lo connected with her first husband, Ojani Noa, an aspiring performer, when he was a waiter at a Miami restaurant in the late ’90s.
They divorced in January 1998 after 11 months of marriage. Then August 2007, Ojani was issued a permanent injunction that forbid him from “criticizing, denigrating, casting in a negative light or otherwise disparaging,” per US. In 2009, J.Lo filed a $10 million lawsuit against Noa for allegedly attempting to sell footage the couple’s honeymoon sex tape, and potentially make it into a film, per The New York Post and The Hollywood Reporter.
Ojani is a Gemini. Leos and Geminis tend to be very theatrical together, according to astrologer Liz Simmons; but, they’ll also be one another’s biggest supporters.
Jennifer Lopez And Alex Rodriguez’s Relationship Timeline, Explained
