Jennifer Lopez‘s romantic life has been a road filled with rocky passages and sharp turns.
The 51-year-old actress and musician looked like she’d finally found Mr. Right when she showed off the enormous ring given to her by fiancé Alex Rodriguez in 2019.
The nuptials to the 45-year-old New York Yankee was set to be her fourth marriage, following a string of high-profile relationships.
Yet with the singer now single again and on the verge of re-igniting her romance with ex-flame Ben Affleck, MailOnline has taken a look at the highs and lows of Jennifer’s quest for love…
Finding love: Jennifer Lopez’s romantic life has been a road filled with rocky passages and sharp turns after splitting from fiancé Alex Rodriguez (pictured in 2019)
Following stints on the CBS crime drama Second Chances and its spin-off Hotel Malibu in the mid-1990s, J-Lo shot to fame with her star-making turns in Selena and the jungle thriller Anaconda, both in 1997.
The Jenny From The Block singer was married to Cuban waiter and occasional actor Ojani Noa for a short period from February 1997 to January 1998.
Though the marriage was brief, it resulted in multiple tasteless legal challenges for the aspiring actress.
First time: The Jenny From The Block singer was married to Cuban waiter and occasional actor Ojani Noa for a short period from February 1997–January 1998 (pictured in 1998)
Following their divorce, Noa worked for Jennifer for six months managing her LA-based Cuban restaurant, Madre’s.
After being fired from the position, he sued for breech of contract and threatened to release both a nude tape of his ex-wife and a tell-all book painting her as a perverted sex fiend.
Slime ball: After being fired from the position, he sued for breech of contract and threatened to release both a nude tape of his ex-wife and a tell-all book painting her as a perverted sex fiend (pictured in 1998)
‘There is revealing video of Jennifer with a lack of clothing and in sexual situations, especially in the hotel footage from the honeymoon,’ said Ed Meyer, an associate of Noa’s, while the tape was on the market.
‘The videos contain salacious material and are going to shock her fans.’
After a six-year legal battle, the Hollywood star was able to block the release of the tape and the tell-all from the ‘gold-digging’ ex.
High profile: While preparing the release of her debut album, On The 6, Jennifer sparked up a relationship with one of its producers, Sean ‘Puff Daddy’ Combs, 51 (pictured in 2000)
While preparing the release of her debut album, On The 6, Jennifer sparked up a relationship with one of its producers, Sean ‘Puff Daddy’ Combs, 51.
The record spawned the number one hit If You Had My Love and established her as a singer to be reckoned with.
Jennifer became an alluring palette for fashion designers during their relationship, and she debuted her most famous outfit during the Grammy Awards ceremony.
The green silk chiffon dress from Versace was super low-cut, extending below her navel and barely covering her cleavage.
Legal scare: The two were charged with criminal possession of a weapon in 1999, though the charges were later dropped against her as she was determined to be uninvolved (pictured in 1999)
Once again, though, Jennifer found herself embroiled in legal issues, this time far more serious.
On December 27, 1999, Jennifer and Sean were arrested following a shooting outside the Times Square Club in Manhattan.
The two were charged with criminal possession of a weapon, though the charges were later dropped against her as she was determined to be uninvolved.
Jennifer broke up with the rap mogul a month before his trial was slated to begin in 2001. He was ultimately acquitted on all charges.
Short-lived marriage: In late 2000, she met Chris Judd, 51, a dancer and songwriter, when he directed her Love Don’t Cost A Thing music video. The two were quickly inseparable, and married on September 29, 2001. By June of 2002 they had split, and the divorce was finalized in 2003 (pictured in 2001)
The Out Of Sight star launched into another short-lived romance immediately following her break-up with Puff Daddy.
In late 2000, she met Chris Judd, 51, a dancer and songwriter, when he directed her Love Don’t Cost A Thing music video.
The two were quickly inseparable, and married on September 29, 2001. By June of 2002 they had split, and the divorce was finalized in 2003.
Bennifer: J-Lo’s most high profile romance was her relationship with Ben Affleck, 48, whom she dated from 2002 to late 2003 (pictured in 2003)
J-Lo’s most high profile romance was her relationship with Ben Affleck, 48, whom she dated from 2002 to late 2003.
The two met on the set of Gigli, their ill-fated romantic comedy that was a critical and commercial bomb.
Ben proposed to Jennifer in November 2002, and media outlets began to refer to the couple as ‘Bennifer,’ launching the era of celebrity couple nicknames.
The two called off their September 2003 wedding ceremony in Santa Barbara, California, only a day before.
The relationship wasn’t meant to be, and they split in January 2004.
Media sensation: Ben proposed to Jennifer in November 2002, and media outlets began to refer to the couple as ‘Bennifer,’ launching the era of celebrity couple nicknames (pictured in 2003)
Following the near-marriage to Ben, Jennifer began her longest relationship to date with Latin singer Marc Anthony, 52.
He became her third husband when the two married in 2004, less than a year after her split from Ben.
In 2008, she and Marc welcomed twins, Maximilian and Emme, now 13.
The couple announced their separation in July 2011, and the divorce was finalized in 2014, with Jennifer retaining physical custody of their two children.
Long-lasting: Following the near-marriage to Ben, Jennifer began her longest relationship to date with Latin singer Marc Anthony, 52 (pictured in 2007)
Growing family: He became her third husband when the two married in 2004, less than a year after her split from Ben. In 2008, she and Marc welcomed twins, Maximilian and Emme, now 13 (pictured in 2005)
Rebound: Following the dissolution of her longest marriage, the Maid In Manhattan star sparked up a more casual relationship with her former back-up dancer Casper Smart, 33, from 2011-2016 (pictured in 2016)
Following the dissolution of her longest marriage, the Maid In Manhattan star sparked up a more casual relationship with her former back-up dancer Casper Smart, 33.
The two were on and off following her separation from Marc in 2011 through August 2016.
In February 2017, Jennifer began dating Alex Rodriguez.
Making it last: In February 2017, Jennifer began dating Alex Rodriguez (pictured in 2019)
She seemed to have something special with Alex. The New York Yankees star fostered a loving, blended family with his soon-to-be wife and her children.
He brings daughters Ella Alexander, 12, and Natasha Alexander, 16, to the relationship. The combined family are often together during outings.
The couple have long hinted they did see a wedding in the future, though have been allowing things to unfold naturally rather then rush into an engagement.
The actress told People in 2019 that the couple would ‘think about getting married… it will happen naturally when and if it’s supposed to.’
Loving couple: She seemed to have something special with Alex. The New York Yankees star fostered a loving, blended family with his soon-to-be wife and her children (pictured in happier times)
Having tied the knot three times, Jennifer explained she wanted to be absolutely certain the fourth time was the charm.
‘I rushed into three different marriages. At this point I want to be sure.’
Yet in March 2021, it was reported that the duo had ‘split’ over his ‘friendship’ with Southern Charm’s Madison LeCroy a factor.
In February, Madison claimed that she spoke with Rodriguez over the phone but insisted it was ‘innocent’ and that he ‘never physically cheated’ on Jennifer.
However, a source told DailyMail.com at the time: ‘Alex has never met or spoken to Madison or anyone from the show.’
In April, the former couple confirmed their split, announcing: ‘We have realized we are better as friends and look forward to remaining so.’
Claims: Yet in March 2021, it was reported that the duo had ‘split’ over his ‘friendship’ with Southern Charm’s Madison LeCroy, pictured, a factor