But soon enough, their romance went downhill and fast. Just one month after their magical prom night– which was one month after they first began dating – they broke up as Drake was reportedly spotted on a date with another woman.
But J.Lo herself wasn’t entirely innocent either, as before her split with Drake had even been announced, Jennifer Lopez was already linked to her ex-fiancé, Alex Rodriguez – endearingly referred to by MLB enthusiasts as A-Rod.
A Modern Renaissance Woman
J.Lo has been called a triple threat and has made quite the name for herself in the entertainment world. She's shown us that the world needs more women who start running things. Jennifer was born in the Bronx as Jennifer Lynn Lopez on July 24, 1969, and her journey began when she started taking singing and dancing lessons when she was just five years old.
Her father was an IT guy, and her mother was a kindergarten teacher. After high school, Jennifer moved to Manhattan, and she would sometimes sleep in the dance studio she practiced at.
Becoming a 'Fly Girl'
She wanted to be the best, and soon enough, Jennifer began working as one of the backup dancers for the up-and-coming boyband "New Kids On The Block." But, her real big break was about to come; she auditioned to be a Fly Girl on the television series "In Living Color."
Jennifer was not chosen initially, but when the show hit its third season, Jennifer officially became Fly Girl; she ended up only staying for one season before leaving the show to pursue an acting career.
The Role of a Lifetime
In 1997, Jennifer landed the role of a lifetime when she got cast as the late Grammy-winning Tejano singer, Selena. Despite having worked with the film's director before, Jennifer still had to go through an intense auditioning process before she was cast in the film. The film is credited as what launched her into stardom.
After filming Selena, Jennifer wanted to pursue singing, and with that, she released her debut single, "If You Had My Love." During the production of her debut album, Jennifer was aware that she received her recording contract based on her looks and an already established name in the entertainment industry. She wanted to prove she had musical talent.
Jennifer's Inspiration
Growing up, Jennifer was heavily influenced by various Latin music styles ranging from bachata to salsa, but it was the 1979 hip-hop song "Rapper's Delight" by The Sugarhill Gang that she said changed her life. Lopez has also said she was influenced by artists such as Tina Turner, Madonna, James Brown, Michael Jackson, and Barbra Streisand.
She was also hugely inspired in her younger years by the 1961 musical film "West Side Story." Lopez has cited Janet Jackson as one of the main inspirations for her own dance, saying that she started dancing because of Jackson's music video for "The Pleasure Principle."
Jen Finds True Love At Last
When it comes to Jennifer Lopez’s romantic life, her path has been paved with many trials and tribulations. Over the years, countless headlines have proclaimed, “Jennifer Lopez Finds True Love At Last” alongside happy photographs. It may be that her rush to the altar is the reason behind the breakdown of her marriage.
Or does she just make bad choices when choosing a partner? With a new ring on her finger, has she finally found the one?
Romantic Problems
If we took one look at J. Lo, it's obvious why she has been married so often; anyone would be happy to be partnered with such a stunning goddess. She's almost perfect – talented, beautiful, and always prepared. So why do her marriages dissolve so quickly, leaving some wondering what's really happening?
It seems she may have finally found happiness now, but problems from her past loves are still haunting her – and there's one man who thinks he can show the rest of the world exactly why.
Not Wasting Any Time
We all know that as we age, we get more life experience, and with that comes the intelligence to distinguish between love and lust. So that might reveal a hint about J. Lo’s first marriage. A young Jennifer must have been a lovely sight thing to behold: a stunning up and coming celebrity with the world, and probably many men, at her feet.
One of these said men was a Cuban waiter named Ojani Noa, who wanted to waste no time when it came to moving things forward.
Ojani's Blackmail
There's no doubt that Ojani was anxious to marry Jennifer so that he could take her off the market. But with any marriage, there is a little thing called divorce that he hadn't contemplated.
This illusion cost J. Lo quite a bit. During their separation, Ojani went on a crusade to find evidence against her that he deemed incriminatory to blackmail her into staying with him. But J. Lo didn't care.
Taking Her to Court
As we would only expect, his cowardly efforts used to convince her to stay had quite the reverse effect, and she sped up the divorce process so that she could reach her the next step: hauling him to court. She had her first victory a few years after the case was presented with a legally binding confidentiality agreement.
It took him a few years to break this into a still-ongoing case today, more than two decades later – but more on that later.
Jen's Broken Heart
But first, Jennifer had to mend her broken heart – some candid photos had been circulating that had the world guessing that she found some comfort in the arms of Sony Music CEO Tommy Mottola. Before they started making public appearances together, Mottola was married to Mariah Carey.
But not without some drama, soon after he was seen with Jennifer, Mariah just so happened to divorce him AND drop her contract with Sony.
Was it Just a Fling?
Nobody had high expectations for Jennifer and Tom, and sure enough, their fling fizzled out before it was even confirmed (fortunately, before Tommy had become too invested in her career). 1999 found Jennifer's career in a great place.
But as she adjusted her focus to her artistry, she got romantic feelings once again, this time with none other than her producer Sean "Diddy" Combs. This time, Jennifer felt that the admiration was clearly for her talent and performance.
Romantic Feelings
At first, only Diddy (then known as Puff Daddy) showed interest; Jennifer was just there to work and wanted to collaborate as professionals. But she was single after all, and it wasn’t long before he won her over. According to them both, they bonded over their shared ambitions and love for the music.
They spent two seemingly blissful years together, and both the couple and the watching world thought he might finally last.
That Dress!
Jennifer was becoming a rising star at this point. On February 23, 2000, Lopez wore an exotic green Versace silk chiffon dress with a plunging neckline on the red carpet of the 42nd Annual Grammy Awards, with Sean "Diddy" Combs accompanying her.
Her dress garnered a lot of controversy and attention, with images of Jennifer in the dress being downloaded over half a million times 24 hours after the event from the Grammy website. Jennifer was surprised by all the media coverage, declaring that she had no idea "it was going to become such a big deal."
Getting Arrested
The couple found themselves really under fire with everyone watching when they were very publicly arrested one night by surprise. When violence was reported near the club they were visiting, somehow, the pair were linked to the crime.
Jennifer was later proven not to be involved, but only after spending the night in custody. Diddy faced a charge ultimately, which poisoned their love to some fans – but others were still rooting for them.
When Puppy Love Isn't Enough
Just after being together for two years, Jennifer admitted to the media that Sean had been unfaithful, bringing the end of their puppy love. Sean has commented on their relationship, saying how much he admired and respected her despite their breakup. Over time, they became friendly again.
Diddy prides himself on his dealings with past relationships, saying, "People gonna grow, and any of my exes, they smile, and they're happy to see me."
Racing to the Altar
Unlike many of her past relationships, Sean Combs still says that she was “without a doubt” one of his great loves. Despite having taken her sweet time with Diddy just earlier that year, by the end of 2001, Jennifer wasted no time finding another match that same year.
Racing to the altar with him just as quickly as she’d switched relationships. But who was this mystery man nobody knew about?
Love Don’t Cost A Thing?
While J. Lo was busy shooting the music video for her new song “Love Don’t Cost A Thing,” one of her backup dancers was Cris Judd – and soon enough, sparks began flying between the star and the dancer. The two started dating, and later that same year, they were married.
But their dancing skills didn’t quite make them marriage material. Cris’ first red flag was as early as their wedding day…
Marriage Material
Cris Judd was never a fan of all attention and publicity surrounding their relationship, and their wedding required a level of security he simply found crazy. He called it a "circus," recalling that, "A few people even got arrested trying to sneak in." They had to rent airspace just to keep their wedding private.
The entire ordeal gave Cris a taste of his future, and he didn't like it at all. While he doesn't blame Jennifer for all the media, it did affect them…and not always in a good way.
Everyone Has Problems
According to Cris, he noticed a theme in her relationships, later commenting, “I can’t give you the answer as to why her relationships didn’t work. Everyone has baggage and problems. It depends on whether you want to deal with those problems.”
In the end, he didn’t want to deal with the problems that came along with dating a celebrity. And he wasn’t alone…
The Newest Power Couple
J. Lo and Cris Judd filed for divorce just nine months after their wedding in June 2002, and soon after, Jennifer started filming "Gigli." Her costar would become her future and possibly her most famous partner, Ben Affleck.
But anybody watching J. Lo's and Ben's relationship unfold could feel the heat rising off of the good-looking pair – they were the new power couple, and cameras couldn't get enough of them.
Bennifer
Jennifer and Ben had quite the love story; they fell in love on-set while filming a movie about their characters falling in love. The pair was called Bennifer, and they couldn’t help but show it once they started falling in love.
Although the infamously problematic film never had good ratings on the big screen, the two paraded their love all while embarking on their creative efforts together.
Being Cautious
J. Lo was a little bit more cautious this time around with Ben, especially considering how she had been with her previous loves, and can we blame her?
Although Jennifer and Ben were engaged within a year since they started dating, they wanted to be patient when tying the knot and slowly let their love continue to grow. During this year of patience, the two realized that they weren't going to last and never got married.
Who's to Blame?
Ben never blamed Jen for their split; she truly felt like the relationship had been her failure. “I was sad,” she said. “I totally lost my sense of self; I even questioned if I belonged in this business, thought maybe I did suck at everything. Our relationship was in front of the entire world and self-destructed for everyone to see.
It took me two years until I could pick myself up again.” Ben blamed their troubles on the paparazzi and how the media infiltrated their relationship. But this was becoming a repetitive obstacle for Lopez. Almost 20 years later in May of 2021, the ex-lovers were seen together, causing talks of them getting back together. Perhaps this time for good?
Jen's Music Style
Much of Lopez's music has been described as autobiographical, focusing on the "ups and downs" of her love life. The lyrical content of "This Is Me..." was largely centered on her past relationship with Ben Affleck, with one particular song, "Dear Ben," being described as the album's focal point.
"Como Ama Una Mujer" was Jen's first full-length Spanish-language album, features reflective lyrics about her romance, heartache, and insecurity.
Speaking of Lopez's Image
Despite a carefully cultivated image as a pop empress donning ludicrously expensive outfits, her signature hits bear the titles "I'm Real" and "Jenny From the Block." She managed the difficult transition from actress to music star without ever having to pick either as her main career.
She established herself as a provocative magnetic figure. At the same time, her demeanor also made it clear that she was a respectable, classy woman.
She is Everywhere
You can forgive yourself if you see Jennifer Lopez in your sleep, as yes, she is everywhere. Ever since her mercurial rise to stardom in the late 90s, Lopez has been deemed the most influential Hispanic performer in the U.S, maybe even the world. She has been credited with breaking ethnic barriers in the entertainment industry.
She's been defined as a multidimensional artist, has become the highest-paid actress of Hispanic descent in history. In 2012, Forbes stated that Lopez "may be the most powerful entertainer on the planet" and named her "the world's most powerful Latino celebrity."
Out Of The Friendzone
Lopez's breakup with Ben Affleck was her "first real heartbreak." But this time, she tried something new: letting herself date someone she could trust, her friend Marc Anthony. Lopez described her next relationship with her longtime friend as an endeavor to "find someone who could make me feel loved and wanted in my loneliest hour..."
When I think back, maybe deep down, I knew that this was a Band-Aid on the cut." She and Anthony married in June 2004, and they lived in Brookville, New York.
Performing for Charity
Following the September 11 attacks, Jen joined various other artists. She was one of the featured artists performing on charitable singles such as "El Ultimo Adios (The Last Goodbye)" and "What's Going On," which benefited people affected by the tragedy.
Proceeds from each ticket sold at her co-headling North American Concert tour with Marc Anthony was donated to "Run for Something Better"—a charitable organization supporting physical fitness programs for children.
What Critics Have to Say
Many critics have deemed Lopez's voice limited and overshadowed by the rest of her music's production while remaining "radio-friendly." Some have remarked that Lopez sticks to the understated humming of a star who doesn't need to sing because she knows you're already paying attention. Meanwhile, others have called her voice "slight," going on to say that "Lopez was never, ever about singing; she was about style."
"Entertainment Weekly" also scrutinized her vocal performance for lacking any of the "husky-voiced sensuality" she has in her films. Many other critics regard Lopez as having a "breathy" stylistic range but lacking personality.
A Demanding Diva
Being a fixture in the tabloids, Lopez has admitted to having a "less-than-perfect" public image. The media often express similarities between J. Lo and actress Elizabeth Taylor due to their numerous failed relationships. She has also received a bad reputation as a demanding "diva," something she denies.
It was once remarked that Lopez is 'Hollywood's most demanding diva'... but Jen still wonders what outrageous crime she has committed to be charged as such a vilified woman in today's culture.
What Made Her a Pop-Icon
Ultimately, she is considered one of dance's "greatest success stories," having ranked second on "11 Of Pop's Most Iconic Dancers" in 2015. Since her youth, J.Lo has felt an emotional connection to dance; she has specialized in ballet, jazz, and flamenco. Since the beginning of her music career, Lopez has been known for emphasizing her body in her music videos, which allowed Lopez to become a dominant musical figure worldwide.
Her diverse choreography encompasses some of the most memorable visuals of the 21st century, with observers stating that her "dancing skills and ability have made her videos an important part of the new millennium's pop icon."
Rumors and Speculations
During the final night of Jennifer and Marc's co-headlining tour on November 7, 2007, they officially confirmed all the speculations and rumors that she might be expecting their first child.
Her father confirmed that the couple was expecting twins, disclosing that it runs in the family: it's a hereditary thing, my sister also had twins." Jen gave birth to a twin boy and girl on February 22, 2008.
Counting Her Blessings
Despite staying married for seven years, Jen and Marc spent most of their time on the rocks. After their divorce, Jennifer even said that she “knew very soon that it wasn’t the right thing.”
Nevertheless, their years together and their strong stance when it came to co-parenting their two children are serious proof that J. Lo had learned some invaluable lessons along her long and winding road. Of course, there was more drama right around the corner…
Wanting to Help
In 2007, Lopez was presented with the Artists for Amnesty prize by the human rights organization Amnesty International for her contribution to the film "Bordertown," which told of all the crime and violence against women in Ciudad Juárez. J. Lo described it as "one of the world's most shocking and disturbing, underreported crimes against humanity."
In 2009, Lopez started the Lopez Family Foundation (originally known as the Maribel Foundation) and her sister, Lynda. The nonprofit organization seeks to improve healthcare availability for disadvantaged women and children, supported by a partnership with the Children's Hospital Los Angeles.
That Time Jennifer and Drake Were Together
J. Lo and Drake were romantically linked in late 2016 and reportedly went on to date for a few weeks. Neither of them addressed their reported romance in depth at the time. With 17 years between them, there are a few reasons why dating Drake was never a good idea – which may be true for any woman since so many winds up featuring in his songs.
But, like many men around the globe, Drake had liked J.Lo since he was a young boy. When he first met her in 2016, it was a moment beyond words for him.
Drake Really Liked Her
Together they embarked on a whirlwind romance. Drake was coming down with a serious case of the feels, and he didn’t hold back when he announced that he thought she was “the real deal.”
But it seems that J.Lo was never that serious about him. While Christmas was just around the corner, he hosted a winter wonderland party with a prom theme, where he even crowned her as queen and himself as king. Now that sounds magical!
One Month Later
But soon enough, their romance went downhill and fast. Just one month after their magical prom night– which was one month after they first began dating – they broke up as Drake was reportedly spotted on a date with another woman.
But J.Lo herself wasn't entirely innocent either, as before her split with Drake had even been announced, Jennifer Lopez was already linked to her ex-fiancé, Alex Rodriguez – endearingly referred to by MLB enthusiasts as A-Rod.
With A-Rod at Her Side
Before we get into her relationship with Alex Rodriguez, her first husband, Ojani Noa, reared his menacing head again. This time, he was threatening to release a video and publish a book from way back on their honeymoon that he's sure will shed some unfavorable light on J. Lo for all the world to see.
Until thus far, Jennifer managed to keep the case under wraps. It really seemed like true love with A-Rod, and it helped keep them unfazed through inevitable rumors about Jen's past.
Her Autograph from 1999
When Rodriguez first met Jennifer, he timidly asked for her autograph. He was still a young baseball player, and he had no idea that they would be a couple one day. Two decades later, he still has her autograph.
They wouldn’t start dating until twelve years later, but Jenny’s been rooting for Alex since the beginning. J.Lo met Alex again at a 2005 baseball game when Alex and the Yankees played against the New York Mets.
Valentine's Day in 2017
Rumors about the new couple started swirling back in February of 2017. Even though they had only been dating for a couple of weeks, A-Rod made sure J.Lo knew he was very serious about her.
Jennifer described arriving at her Vegas dressing room with bouquets, candied chocolates, and a cake to top it all off if that wasn't enough. Jen said, "Who sent me all that? I didn't know who it was because our relationship was still new."
Doing More Together
As they say, the couple that stays together birthdays together. Because Jen and Rodriguez's birthdays are so close to one another, they shared a birthday party in July 2017. They're both Leo's as Lopez's birthday is on July 24, while Rodriguez's birthday is July 27.
Just three months later, the couple began taking steps to move in together. It seems to be getting serious now that they are starting to make more financial decisions together.
What Does Love Look Like?
When they were together, Jennifer and A-Rod did a good job showing the rest of us what true love actually looks like. On his birthday in 2020, Jen wrote, “Every day, I am surprised by the loving, generous person you are to me and everyone around you.”
Until the day they broke up, he kept telling family and friends, “Jen makes me feel like a kid again.” After a romantic beach proposal and a massive engagement ring, fans were sure that this would be the relationship that lasted.
J. Lo's Legacy
Jennifer has sold over 70 million records worldwide as of 2017, and her films have earned a combined total of US $3.1 billion. She prevails as the only female performer to have a number one album and movie simultaneously.
With her second studio album "J.Lo," she became the first solo recording artist with Epic Records to produce a number one album in the U.S. since the label's beginning in 1953.
A-Rod's MLB Success
The amorous union of the two native New Yorkers has been reported as quite the megamerger in Hollywood. Of course, anyone would be intimidated by J. Lo and her impressive career, but not A-Rod.
Rodriguez has also experienced quite the slew of success as the highest-paid player in MLB for years. He has also been ranked as the 16th highest-paid professional athlete ever, earning around $600 million during his baseball career.
Their Engagement
In March 2019, Lopez and Rodriguez officially became engaged. While they were on their beach holiday in the Bahamas, Rodriguez asked Lopez to marry him.
Naturally, the two posted photos of their engagement on Instagram, where fans were indulged with all the juicy details of their proposal and Jen's stunning diamond ring.
Rumors of Cheating
So after two years together, the two are finally engaged. J.Lo announced that she wants to expand her fam with A-Rod. According to sources, Lopez's diamond ring is reported to be about 15 carats and could be worth a whopping 1.4 million dollars. Jen stated that she's in no rush to get married, especially since she's been married three times before. Perhaps this was an indicative sign of the inevitable.
Their fairytale came with some heartbreaking news when former Yankees baseball player Jose Canseco accused Rodriguez of cheating on Lopez just a day after the couple announced their engagement.
Setting a Date
J-Rod did not comment on the allegations. But they did change her view on marriage. Lopez declared that her feelings about the wedding evolved after Rodriguez proposed. She elaborated that she thought they would get married a couple of months after their engagement...
But then Jen remembered that she's a hopeless romantic, which is why she's been married three times before.
A Wedding in Italy
Months before their highly-covered breakup, a source has told "Us Weekly" that the couple was preparing an extravagant ceremony in Italy. Apparently, they had been organizing and planning it all for a later date.
Unfortunately, it had been planned out and paid for, just waiting for the right time to get married, but perhaps they waited too long.
The Unfortunate Breakup
Fans thought that Jen had found her forever love, and so did she. Unfortunately, after months of rumors that the couple had split, they announced their split in April 2021. Fans were shocked and heartbroken, to say the least, but real J. Lo fans knew that their beloved singer was going to do what was right for her.
The reason behind their breakup? Rodriquez's reputation as a cheater was fatal to their relationship; Jen couldn't trust him. Though we know that the former power couple is doing what is right for them, we can't help but mourn what could have been one of the greatest love stories in Hollywood history.
The Almighty Ben Affleck and Jennifer Lopez
The 2000s are officially back baby! After 17 years apart, the pair recently sparked rekindling rumors. Then "Bennifer" went ahead and set those rumors ablaze and broke the internet with the announcement that the two were engaged once again.
The two look oh, so very, very, very happy, as seen on J-LO Insta's page. It's been reported that Ben dished out $10 million dollars on an 8.5-carat emerald green engagement ring to pop the question. It was obviously answered in the affirmative and the two finally said their I dos in a small ceremony in the summer of 2022.
Or Not
Despite everyone's hopes and well wishes, the second time around did not make it in the long run for Ben Affleck and Jennifer Lopez. After 2 years of marriage, the couple broke it off yet again. It appears that the two separated in April 2024 but the official file for divorce was in August of that same year.
What a roller coaster of a relationship! While separation is usually not a happy occasion, if these two found their way back to each other 20 years after the first time, who's to say what the future holds for them? Never say never.