By Brian Marks for Dailymail.com
Posted: 05:52, 10 March 2019 | Updated: 05:27, April 9, 2022
Jennifer Lopez’s romantic life is a road filled with rocky passages and sharp turns.
And the 52-year-old hitmaker shocked the world last year when she called off her engagement to New York Yankee Alex Rodriguez and rekindled her relationship with Ben Affleck.
Now that Jennifer has confirmed she is engaged to the 49-year-old Oscar winner for the second time, MailOnline looks at all the highs and lows of Jennifer’s quest for love…
Highs and lows: After Jennifer Lopez recently confirmed she’s engaged to actor/director Ben Affleck for the second time, MailOnline takes a look at all the highs and lows of the 52-year-old singer’s quest for love
After starring in the CBS crime drama Second Chance and its spinoff Hotel Malibu in the mid-1990s, J-Lo shot to stardom with starring roles in Selena and the jungle thriller Anaconda, and both in 1997.
The Jenny From The Block singer was married to Cuban waiter and occasional actor Oyani Noa for a brief period from February 1997 to January 1998.
Although the marriage was short-lived, it led to numerous tasteless legal challenges for the aspiring actress.
First Time: The Jenny From The Block singer was married to Cuban waiter and occasional actor Oyani Noa for a brief period from February 1997 to January 1998 (pictured in 1998)
After their divorce, Noah worked for Jennifer for six months, managing her Los Angeles-based Cuban restaurant Madre’s.
After being fired from the position, he sued for breach of contract and threatened to release both a nude tape of his ex-wife and a book describing her as a perverted sex fiend.
Slime Ball: After being fired from the position, he sued for breach of contract and threatened to release both a nude tape of his ex-wife and a book describing her as a perverted sex demon (pictured in 1998)
“There’s revealing footage of Jennifer naked and in sexual situations, especially the honeymoon hotel footage,” Noah’s collaborator Ed Meyer said while the tape was on the market.
“The videos contain indecent material and will shock her fans.”
After a six-year legal battle, the Hollywood star was able to block the release of the tape and reveal everything from the “gold digger” ex.
High profile: While preparing the release of her debut album On The 6, Jennifer began 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 began 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 at the Grammys.
The green Versace silk-chiffon dress was super low-cut, reaching her navel and barely covering her cleavage.
Legal scare: The pair were charged with criminal possession of a weapon in 1999, although the charges were later dropped against her as it was determined she was not involved (pictured in 1999)
Once again, however, Jennifer found herself involved in legal problems, this time much more serious.
On December 27, 1999, Jennifer and Sean were arrested after a shooting outside the Times Square Club in Manhattan.
The two were charged with criminal possession of a weapon, although the charges were later dropped against her as it was determined she was not involved.
Jennifer broke up with the rap mogul a month before his trial began in 2001. He was eventually acquitted of 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 2002, they had separated and the divorce was finalized in 2003 (pictured in 2001)
The Out Of Sight star embarked on another short-lived romance right after her split 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 2002, they had separated and the divorce was finalized in 2003.
Bennifer: J-Lo’s most famous romance was her relationship with Ben Affleck, 48, who she dated from 2002 to late 2003 (pictured in 2003)
J-Lo’s most famous romance was her relationship with Ben Affleck, 49, 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 the media began calling the couple “Bennifer,” ushering in the era of celebrity couple nicknames.
The two called off their September 2003 wedding ceremony in Santa Barbara, California, just a day before.
The relationship was not meant to be at the time and they split in January 2004.
But 17 years later in May 2021, the former Hollywood power couple rekindled their famous romance.
Media sensation: Ben proposed to Jennifer in November 2002 and the media started calling the couple ‘Bennifer’, ushering in the era of celebrity couple nicknames (pictured in 2003)
After almost marrying Ben, Jennifer began her longest relationship to date with Latin singer Marc Anthony, 52.
He became her third husband when the two tied the knot in 2004, less than a year after her split from Ben.
In 2008, she and Mark welcomed twins Maximilian and Emme, who are now 13 years old.
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: After almost marrying 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 tied the knot in 2004, less than a year after her split from Ben. In 2008, she and Mark welcomed twins, Maximilian and Emme, now 13 (pictured in 2005)
Bounce: After the break-up of her longest marriage, the Manhattan Maid star began a more casual relationship with her former backup dancer Casper Smart, 33, from 2011-2016 (pictured in 2016)
After the breakup of her longest marriage, the “Manhattan Maid” star began a more casual relationship with her former backup dancer Casper Smart, 33.
The two were on and off after her split from Mark in 2011 until August 2016.
In February 2017, Jennifer began dating Alex Rodriguez.
To move on: In February 2017, Jennifer started dating Alex Rodriguez (pictured in 2019)
There seemed to be something special about Alex. The New York Yankees star has created a loving, blended family with his future wife and her children.
He brings daughters Ella Alexander, 12, and Natasha Alexander, 16, into the relationship. The blended family is often together during outings.
The couple has long hinted that there will indeed be a wedding in the future, though they’ve been letting things play out naturally rather than rushing 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 needs to.”
Couple in Love: She seemed to have something special with Alex. The New York Yankees star has created a loving, blended family with his wife-to-be and her children (pictured in happier times)
Having been married three times, Jennifer explained that she wanted to be absolutely certain that 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 “broken up” over his “friendship” with Southern Charm’s Madison LeCroy.
In February, Madison claimed she spoke to Rodriguez on the phone, but insisted he 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’ve realized we’re better friends and look forward to staying that way.”
Claims: Yet in March 2021 it was reported that the duo had ‘broken up’ over his ‘friendship’ with Southern Charm’s Madison LeCroy, pictured, factor
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