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Who are all of Jennifer Lopez’s ex-boyfriends? Take a trip down memory lane

Now that JLo and Ben Affleck are married, let's take a look back at the men who were lucky enough to date Jenny From The Block.
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Fifth time’s a charm right?

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Jennifer Lopez sent the internet into meltdown when it was revealed she and Ben Affleck got married on July 16, 2022 – nearly two decades years after calling off their wedding.

The couple, who rekindled their romance last year after breaking up in 2004, tied the knot in an intimate ceremony in Las Vegas.

“It was super, super small,” an insider told Page Six. “[Jennifer’s] mom and kids were there. They just wanted to be married so they got married.”

Jennifer announced her engagement in April via her OnTheJLo newsletter, posting a video featuring her glittering 8.5-carat green diamond engagement ring, a colour that holds special significance for her.

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In a previous newsletter, JLo admitted: “I’ve realised there are many moments in my life where amazing things happened when I was wearing green.”

For those keeping track, this is the Grammy-nominated songstress’ seventh proposal, sixth ring, and her fourth marriage.

She and Ben may be marriage goals right now, but who were the men that had the privilege to date and even propose to Jenny From The Block over the years? Let’s meet them here…

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(Image: Getty Images)

David Cruz

Back in the eighties, Jennifer Lopez’s main man was her high school sweetheart relationship David Cruz, who she dated from the age of 15 well into her early 20s. Even after their break up, Jennifer said that he “is a friend and he probably knows me better than anyone else.”

(Image: Getty Images)

Wesley Snipes

After David came her Money Train costar Wesley Snipes, who she dated in 1995 and who she also performed her first ever sex scene with.

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(Image: Getty Images)

Ojani Noa

Jennifer’s first marriage from February 1997 to January 1998 was with Cuban waiter Ojani Noa.

(Image: Getty Images)

Ojani Noa

The two fell madly in love before Jen got her big break in the 1997 biopic hit Selena, but divorced soon after. In 2006, JLo even sued Ojani to stop him from publishing a tell-all book about their marriage and releasing a sex tape from their honeymoon.

(Image: Getty Images)

Tommy Mottola

Not long after her split with Ojani, Jennifer had a short fling in 1998 with Tommy Mottola, Mariah Carey’s ex-husband. Maybe this is why the two pop divas have never gotten along…

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Sean Combs

Who could forget this outfit? Jennifer’s iconic Versace gown was accessorised by her high-profile boyfriend Sean Combs back when he was Puff Daddy. The couple dated from 1999-2001 but had their fair share of drama. Both were charged in connection with a Manhattan nightclub shooting, though charges against JLo were quickly dropped after questioning.

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Sean Combs

RIP to the ultimate late nineties/early noughties hip hop couple.

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Chris Judd

Soon after Diddy, Jennifer fell for Chris Judd, a back-up dancer in her music video Love Don’t Cost A Thing. They tied the knot in 2001 but after nine short months, the couple split.

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Ben Affleck

They may have made one of the least critically acclaimed movies ever with Gigli, but Bennifer (round one) were the ultimate power couple of the early noughties. Ben Affleck even starred in her Jenny From The Block music video.

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Ben Affleck

The couple became engaged in 2002 and Ben proposed with a 6.1-carat pink diamond ring, worth a reported $1.2 million. But after two years of being in the public eye, they broke it off, with Jen even calling the ordeal her “first big heartbreak.”

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Ben Affleck Looks Back at Jennifer Lopez Romance

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Jennifer Lopez Opens up About Her Engagement to Ben Affleck

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Marc Anthony

Jen found love with her longtime friend Marc Anthony, with the two marrying in June 2004, mere days after Anthony finalised his divorce from his first wife Dayanara Torres.

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Marc Anthony

They welcomed twins Max and Emme in 2008 but ended their marriage in 2011. However, the Latin superstars have remained on good terms and even shared an onstage kiss during the Latin Grammys in 2016.

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Casper Smart

In 2011, the On The Floor hitmaker fell for another one of her back-up dancers, Casper Smart, who was 18 years her junior. The couple dated on and off for six years.

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Casper Smart

They enjoyed a low-profile romance, with JLo revealing that neither of them are into those wild Hollywood parties. “We don’t get wrapped up in the Hollywood life that can chew you up and spit you out. I’ve seen it happen a million times,” Smart revealed during their relationship.

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Jennifer Lopez on dating younger men

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Maksim Chmerkovskiy

Though it was never made official, there were rumours that Jennifer was dating dancer Maksim Chmerkovskiy, after the two were spotted getting cosy at a nightclub in 2014 and then again at the Grammy-nominated superstar’s 45th birthday party.

“She’s great, I have fun,” he said. “And while other names are out there … I am not a scumbag,” Maksim said when asked about the rumours.

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(Image: Instagram)

Drake

After JLo uploaded this snap of Drake locking her in a cute cuddle in 2016, the internet went into meltdown. Turns out it was most likely a fling, but that didn’t stop the rapper from spoiling the Ain’t Your Mama singer with a $100,000 Tiffany Victoria necklace while spending New Year’s Eve together in Las Vegas.

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Alex Rodriguez

JLo met Alex Rodriguez, a former baseball superstar who dated the likes of Cameron Diaz, Kate Hudson and Madonna, in 2005 back when she was still married to Marc Anthony. The two reconnected in 2017.

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Alex Rodriguez gushes about girlfriend Jennifer Lopez

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Alex Rodriguez

After two years of dating, ARod popped the question with a four million dollar ring on a trip to the Bahamas. However the couple called it quits in early 2021.

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(Image: Instagram)

Ben Affleck 2

In April 2021, fans went wild when it was revealed Bennifer were back on. The couple went Instagram official with this snap in July that year and began to attend numerous red carpet events together.

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Ben Affleck 2

Take two! JLo and Ben announced their engagement in April 2022.

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Ben Affleck 3

Bennifer tied the knot in an intimate ceremony in Las Vegas on July 16, 2022. “It was super, super small,” an insider told Page Six of the nuptials. “[Jennifer’s] mum and kids were there. They just wanted to be married so they got married.”

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