Jennifer Lopez may have ruled Hollywood with her singing and acting chops, but when it comes to her dating history, her search for a “True Love” is still underway.
While collecting awards and earning herself the status of a pop icon, JLo has also dealt with numerous heartbreaks and broken marriages. However, she remained consistent with her choice of men.
One look at her dating history shows that Jennifer Lopez has a flair for the high rollers, having been linked with Hollywood’s top-tier stars like Ben Affleck, Marc Anthony, and Drake, among others. Her link-up with Affleck remains one of the most popular romances in Hollywood, having gone through the same tragic love story twice.
With Lopez filing for divorce from the Deep Water actor in August 2024, it’s the perfect time to take a thorough look at the dating history of Jennifer Lopez which consists of four marriages and six engagements.
Revisiting the dating history of Jennifer Lopez by looking at her ex-boyfriends
Before diving deep into the dating history of Jennifer Lopez over the years, let’s take a quick look at the relationship timeline of the “Jenny From The Block” singer.
- Ojani Noa: 1997
- Sean “Diddy” Combs: 1999 to 2001
- Cris Judd: 2001 to 2002
- Ben Affleck: 2002 to 2004 and 2021 to 2024
- Marc Anthony: 2004 to 2011
- Beau ‘Casper’ Smart: 2011 to 2016
- Drake: Speculated in 2016
- Alex Rodriguez: 2017 to 2021
1. Ojani Noa (1997)
Profession: Personal trainer and former model
How did they meet: At Gloria Estefan’s Cuban restaurant
Ojani Noa is Jennifer Lopez’s first husband. Noa was a 22-year-old when he met a 28-year-old JLo at Gloria Estefan’s Cuban restaurant on Miami’s famous Ocean Drive in 1996. She was already a popular figure at the time. Noa landed a job as a dishwasher at the restaurant while hustling as a model on the side. It was almost love at first sight for the pair.
The duo got married in February 1997 but got divorced 11 months later. In an interview with The Daily Mail in 2022, Noa blamed fame and money for the downfall of their marriage. He also mentioned Lopez’s dates with rapper Sean Combs, known as P. Diddy, caused a rift between them.
In the same interview, Noa reacted to Lopez’s wedding to Affleck and predicted their divorce. He said, “I wish her and Ben the best, but I’m not convinced it will last.” He did not mince his words while evaluating his ex-wife’s tendency to fall in and out of love quickly.
He added, “Jen loves being in love but she’s been engaged six times. Ben is husband number four. I was husband number one and she told me I was the love of her life.”
2. Sean “Diddy” Combs (1999 to 2001)
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Profession: Rapper
How did they meet: On the set of the music video “If You Had My Love”
JLo went public with her relationship with rapper Sean Combs shortly after parting ways with her first husband. Lopez’s relationship with Diddy was the talk of the town as they became hip-hop’s power couple. Diddy was also in the frame during JLo’s sultry green Versace dress moment at the 2000 Grammys.
After dating for two years, the couple called it quits. In a 2003 interview with Vibe magazine, Lopez talked about Diddy’s unfaithful acts during their relationship. “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,” she revealed to the magazine.
The duo moved on and remained friends over the years. Diddy is currently the subject of a federal sex trafficking investigation. This is not his first brush with the law as he was acquitted back in 2001 in connection with the infamous 1999 shooting outside a nightclub in New York City which also involved JLo.
American record executive Suge Knight, Combs’ rival, made bold claims about Diddy’s possible involvement in Lopez’s divorce with Affleck in August 2024. On his podcast, Collect Call With Suge Knight, he claimed that Affleck may have gotten his hands on Diddy’s FBI tapes which allegedly contain videos of Lopez’s past actions.
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By Kratagya Rathore | Aug 06, 2024 | 9 min read
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3. Cris Judd (2001 to 2002)
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Profession: Dancer and actor
How did they meet: On the set of “Love Don’t Cost a Thing” music video
Lopez fell in love with her backup dancer, Cris Judd, while shooting for the music video. The couple tied the knot in September 2001. But their romance was over just as soon as it was started, becoming one of the shortest marriages in Hollywood. The duo parted ways in June 2002 and their divorce was finalised in 2003.
In an interview with Us Weekly in September 2014, Judd gave a crisp statement about his short-lived marriage with Lopez. He said, “Unfortunately, it just didn’t work out”.
4. Ben Affleck (2002 to 2004 and 2021 to 2024)
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Profession: Actor and filmmaker
How did they meet: On the set ofGigli
Jennifer Lopez and Ben Affleck‘s whirlwind romance can inspire an epic film. Considered one of the greatest romances in Hollywood, JLo and Affleck even earned a couple’s name for themselves — Bennifer.
Lopez met The Accountant star on the set of their 2002 film Gigli. She was married to Judd at the time. After her divorce from Judd in June 2002, JLo took no time to “Live It Up” with Affleck.
The duo got engaged within a few months of dating. The entire world believed JLo finally found her soulmate after two failed marriages. However, the two delayed their wedding just four days before the D-day in September 2003.
Subsequently, the couple called off their engagement in January 2004.
Almost two decades later, in a 2022 interview with Rolling Stone, Jennifer Lopez reflected on her failed engagement with Affleck by saying, “We were so in love, but also, there was this other thing happening where we were being criticised, and it really destroyed our relationship from the inside out because we were just too young to understand at that time what were really the most important things in life.”
But this wasn’t the end for ‘Bennifer’.
Lopez reunited with her old flame after almost two decades. From Montana to Miami, the rumours of their romantic escapades spread like wildfire, flaring the speculations of their reconciliation in 2021, a landmark chapter in the dating history of Jennifer Lopez.
On her 52nd birthday, Lopez made things official by sharing a steamy picture of the two kissing on her Instagram. The couple decided to give their romance another chance. But they didn’t learn any lessons from the last tragedy as they repeated their fate by getting engaged in April 2022, just two months after reconciling.
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‘Bennifer 2.0’ officially tied the knot on 16 July 2022 in a late-night ceremony in Las Vegas. Things seemed serious this time as Lopez even took on her husband’s last name.
But the second time was also not a charm for ‘Bennifer’ as their relationship, once again, ended on an even sour note. According to a report from TMZ, Lopez filed for divorce from Affleck in August 2024 in L.A. County Superior Court on their second wedding anniversary.
The date of their separation is listed as 26 April 2024. As per Lopez’s documents, the couple, who are not even on talking terms, did not have a prenup. The duo will go through the tedious legal procedures of sorting out their finances from the last two years.
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5. Marc Anthony (2004 to 2011)
Profession: Singer and songwriter.
How did they meet: On the set of the Broadway production of The Capeman.
Marc Anthony and Lopez bonded over music and their first collaboration was on the song “No Me Ames” from the latter’s 1999 debut album On the 6. However, things between them didn’t turn romantic right after.
Anthony got married to former Miss Universe, Dayanara Torres in 2000 and got divorced in 2004. This was around the same time Lopez called it quits with Affleck. Soon after the Selena star reconnected with Anthony but kept the relationship low-key. They got married in June 2004 and had their first performance together as a married couple at the 2005 Grammy Awards.
On 22 February 2008, Lopez and Anthony welcomed twins Emme and Max. The couple announced separation in July 2011.
In an interview with W magazine in 2016, Lopez candidly spoke about her third failed marriage and how it led to major disappointment. She said, “When my marriage (to Anthony) ended, it was not easy to find forgiveness. It wasn’t the dream that I had hoped for, and it would have been easier to fan the flames of resentment, disappointment and anger.”
The pair’s divorce was finalised over three years later in June 2014. They remained cordial over the years and also co-parent their twins.
6. Beau ‘Casper’ Smart (2011 to 2016)
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Profession: Dancer
How did they meet: Unknown
Jennifer Lopez added another backup dancer to her dating history in November 2011, just four months after splitting with Marc Anthony.
Lopez was 42 while Smart was 24 when they started dating. Despite the age gap, the pair went strong for a couple of years before breaking up in 2016.
According to a 2016 report from People magazine, “It (the break-up) wasn’t anything dramatic and they were on good terms – it just came to a natural end. They will remain friends and they see each other, but they are not together. It was very amiable.”
7. Drake (2016)
Profession: Rapper
How did they meet: Backstage at Lopez’s All I Have show.
Perhaps it was “God’s Plan” to put Drake and JLo together for the most dramatic and unexpected fling in Hollywood. The duo met in December 2016 when Drake attended Lopez’s All I Have show.
The duo was soon rumoured to be happily dating. However, a 2017 Us Weekly report claimed that the relationship “died down a bit” after Drake embarked on his European tour. Their chapter was seemingly closed… until Lopez’s divorce from Affleck started making the headlines.
A 2024 In Touch report claimed that Drake is hoping to get a second chance to have “One Dance” with Lopez. “But once things are officially done with Ben (Affleck), he’ll be ready and waiting to show her a good time,” the report claimed. Now that the divorce is underway, fans will have to wait and watch for the rapper’s next move.
8. Alex Rodriguez (2017 to 2021)
Profession: Former baseball player
How did they meet: At a baseball game
Alex Rodriguez and Jennifer Lopez crossed paths at the Shea Stadium in Queens, New York, in May 2005 when the latter attended a baseball game with her then-husband Marc Anthony. In an interview with Sports Illustrated in June 2019, Lopez looked back at her first meeting with Rodriquez and admitted there was a “weird electricity” between the two.
The duo met again in February 2017 at a restaurant. They apparently revived the electricity as they soon started dating. They made their Met Gala debut as a couple in 2017 and instantly became Hollywood’s new favourite couple. Things appeared serious between them as they were seen hanging out with each other’s kids.
This time, JLo was taking things slow as she told Harper’s BAZAAR in 2018, “I do believe in marriage, and I would love to grow old with somebody in a committed relationship. But I’m not forcing anything right now. It’s good, it’s healthy.” In March 2019, the couple announced their engagement.
Their wedding was postponed a couple of times due to the coronavirus pandemic. Fans were loving JLo and Rodriguez’s relationship. But, in a heartbreaking move, the couple called off their two-year engagement in April 2021.
In a joint statement to the Today show. the pair stated, “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.”
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(Header and feature image courtesy: Instagram and X/Jennifer Lopez)
The information in this article is accurate as of the date of publication.
