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Jennifer Lopez’s dating timeline as she ‘works through things’ with Alex Rodriguez

Jennifer Lopez relationship timeline
Jennifer has had some high-profile relationships (Picture: Rex)

We thought Kimye’s divorce would be the most shocking celebrity split of the year – then came Jennifer Lopez and Alex Rodriguez.

It was reported that the couple had split after four years together and two years after they got engaged, after postponing their wedding twice due to Covid-19 restrictions.

This blindsided fans who believed Jennifer, 51, and Alex, 45, were blissfully loved up, having last been seen cuddling in the Dominican Republic last month.

Now, the pair have claimed it’s not over yet, and they are ‘working through some things’.

Jennifer’s love life has long been in the headlines due to her famous partners and high-profile engagements, but she knows the importance of loving herself more.

She told Harper’s Bazaar in 2019: ‘For me, the relationship journey has been very up and down. But it didn’t have to do with anybody else but me — it was about me figuring out me. Until you learn to love yourself, you can’t completely love [someone else] in a way that is pure and true. ‘Once you do that, you can have relationships that are based on love and respect, that are supportive and nourishing. There’s an evolution there that had to happen for me.’

Here is a rundown of JLo’s marriages and relationships in the spotlight.

Ojani Noa

Jennifer has taken legal action against her first husband (Picture: Steve Granitz/WireImage)

In 1997, Jennifer married Cuban waiter Ojani Noa, but just 11 months later, they split up.

Since then, JLo has had numerous legal issues with her ex, and in 2006, she sued him to prevent Ojani writing a book about their relationship.

The following year, Ojani was issued a permanent injunction forbidding him from ‘criticising, denigrating, casting in a negative light or otherwise disparaging’ his ex-wife.

Sean ‘Diddy’ Combs

Singer/actress Jennifer Lopez (L) poses with her b
Talk about a power couple (Picture: Vince Bucci/AFP via Getty Images)

One of the most high-profile couples of the late nineties, JLo and Puff Daddy, as he was then known, began dating in 1999 after meeting on the set of a music video.

However, they split in 2001, with Jennifer later accusing the rapper of cheating on her.

She told Vibe magazine in 2003: ‘It was the first time I was with someone who wasn’t faithful. I was in this relationship with Puff where I was totally crying, crazy and going nuts, it really took my whole life in a tailspin.

‘I had to think, do I want to be home with kids in 10 years wondering where somebody is at three in the morning?’

Cris Judd

Jennifer Lopez weds Cris Judd
Jennifer and Cris’s marriage lasted less than a year (Picture: Joe Buissink/WireImage)

Jennifer rebounded with dancer Cris, who she met on the set of her video for Love Don’t Cost A Thing, and the pair tied the knot in September 2001.

Their marriage was short-lived, though, and the couple split in June 2022, with their divorce being finalised the following year.

Cris – who has since remarried – said their marriage ‘just didn’t work out’, while jennifer said: ‘Coming out of a torrid relationship, I meet this sweet person who’s so refreshing. But marriage is not just about love. I thought I had learned that in my first marriage…. I loved Cris, still love him, he’s one of the best people. This wasn’t an easy thing to walk away from, but we didn’t have what it takes to make a marriage work.’

Ben Affleck

Jennifer Lopez and Ben Affleck Split
Bennifer broke things off months after they called off their wedding (Picture: Kevin Winter/Getty Images)

Months after splitting from Cris, Jennifer met Ben Affleck on the set of the soon-to-be critically panned film Gigli, and thus began one of the most publicised relationships in Hollywood – Bennifer.

Their romance coincided with the rise of the internet and tabloid magazines, and they were basically ominpresent, with Ben famously starring in JLo’s video for Jenny From The Block.

Things reached fever pitch as they prepared to get married, after a year’s engagement.

However, their wedding in September 2003 was called off with four days to go due to ‘excessive media attention’, and Bennifer split four months later.

Speaking about the attention their relationship received, Oscar winner Ben said: ‘You know, there’s always a story of the month, and me dating Jennifer Lopez happened to be that tabloid story at the time when that business grew exponentially. 

‘Still, to this day, [some] will go, “I see you out there in the paparazzi and the pictures!” It’s like, “Yes, I left my house and took out the trash. It’s not like I’m trying to…” And it’s still like, “You were taking a pap walk!”’

After Ben’s split from JLo, he began dating another Hollywood Jen, Jennifer Garner, and the pair tied the knot in 2005, going on to welcome three children together before splitting in 2015.

Marc Anthony

68th Annual Golden Globe Awards - Arrivals
Jennifer and Marc have two kids together (Picture: Jason Merritt/Getty Images)

Soon after Jen’s split from Ben, she found solace with her long-time friend, singer Marc Anthony, and in June 2004, they got married.

Three years later, they announced they were expecting twins and in 2008, Max and Emme were born.

Three years on from that, Jennifer and Marc split, with the Maid In Manhattan star filing for divorce in April 2012.

The divorce was finalised in 2014, and Marc and Jennifer continue to co-parent their children, who are now 13.

Casper Smart

70th Annual Golden Globe Awards - Arrivals
Jennifer and Casper had an on again off again relationship (Picture: Jeff Vespa/WireImage)

Months after her separation from Marc, Jennifer began a five-year on and off romance with backup dancer Casper Smart.

Throughout their romance and various break-ups, Casper continued working with Jennifer and was even hired as the creative director for her residency in Las Vegas.

They broke things off for good in 2016, but remained on good terms.

Drake

Drake 'Euphoria' TV Show Premiere, Arrivals, Pacific Cinerama Dome, Los Angeles, USA - 04 Jun 2019 Mandatory Credit: Photo by MediaPunch/REX (10268592q)
Jennifer reportedly had a fling with Drake (Picture: MediaPunch/REX)

Although their romance was never confirmed, Jennifer was linked to Drake in December 2016, after the rapper posted a picture of them cuddling on a sofa.

It’s believed their brief relationship fizzled out just a few months later, with Jennifer joking that the rapper was a ‘booty call’ when Hotline Bling played during her show.

Drake also alluded to their fling on the track Diplomatic Immunity, rapping: ‘2010 was when I lost my halo / 2017 I lost a J. Lo / A Rotterdam trip had me on front page, though.’

Alex Rodriguez

Alex proposed in 2019 (Picture: Dimitrios Kambouris/Getty Images)

Baseball star Alex asked Jennifer out on a date after they started chatting in early 2017, and the pair confirmed their relationship in March.

In May that year they made their red carpet debut together at the Met Gala, and that year, Jennifer and her children and Alex and his daughters Ella and Natasha came together to celebrate Thanksgiving as a blended family.

After plenty of loved-up posts and red carpet PDAs, Alex popped the question in March 2019, and had planned to get married in 2020 – but the pandemic forced the couple to postpone their wedding twice.

Then came the news that Jennifer and Alex had parted ways, after a rocky few months – but now, the pair have stated: ‘All the reports are inaccurate.  We are working through some things.’


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