Jennifer Lopez and Ben Affleck’s romantic timeline from split to second chance

Jennifer Lopez shares skincare tutorial

Jennifer Lopez was married three times before tying the knot with Ben Affleck, 50, last year – but their romance with goes back more than two decades.

The Hollywood power couple enjoyed their first wedding anniversary earlier this month, proving to be more loved-up than ever after finally reuniting.

Now both stars are thriving in their 50s, how exactly did ‘Bennifer’s’ illustrious relationship history reach this point?

Here’s the full rundown – from make-up to break-up and back again.

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First Marriages

Lopez was actually married to both waiter Ojani Noa and former backup dancer Cris Judd before she started dating Affleck.

Noa was married to the Hustlers star from February 1997 to January 1998, whilst her marriage to Judd lasted a little longer – September 2001 to January 2003.

She was also in an on/off relationship with record producer Sean Combs aka Puff Daddy, but Lopez said she always knew their ‘crazy, tumultuous’ relationship would end at some point.

Her divorce from Judd was finalized in 2003, by which point she had started dating Affleck several months earlier.

Bennifer Begins

The Hollywood stars had already crossed paths several times before while their careers were taking off.

They became familiar in 1998 after meeting at the Academy Awards, and at the premiere of Affleck’s film Armaggedon.

However, Lopez and Affleck’s sizzling chemistry didn’t become clear until they co-starred in the 2003 film Gigli.

Filming began in 2001 and it didn’t take long for the sparks to start flying.

Although the film was critically panned and was a box office bomb, it launched a Hollywood love story for the ages.

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End of Engagement

Tabloids soon dubbed the couple ‘Bennifer’ when the pair became attached at the hip.

They collaborated several times throughout their relationship, including on Kevin Smith’s 2004 film Jersey Girl, and with Affleck appearing in JLo’s iconic music video for Jenny from the Block.

Lopez and Affleck were engaged in November 2002 but, sadly, it wasn’t to last – this time.

Their planned wedding in September 2003 was postponed due to unwanted media attention, and the engagement was called off altogether in January 2004.

Affleck’s unease with the press is considered one of the biggest factors of their split, with J.Lo calling it her “first real heartbreak”.

Happy Families

After their engagement was called off, it didn’t take long for Bennifer to go their separate ways and start settling down.

Lopez was married to singer and actor Marc Anthony for 10 years between 2004-2014, although they separated in 2011.

They share fraternal twins, a boy and a girl, and Lopez gained primary custody after their divorce was finalized in 2014.

Meanwhile, Affleck was starting a family of his own with his A-Lister wife Jennifer Garner.

Affleck and Garner were married in 2005 after becoming friends on the sets of Pearl Harbor and Daredevil, but split in June 2015.

They share joint custody of their three children, though Affleck described the divorce as “a painful experience” and “the biggest regret of my life”.

Fleeting Flings

Both stars suddenly found themselves single after several years of marriage in the 2010s.

From 2011-2016, Lopez had an on-off relationship with another former backup dancer, Casper Smart, before dating New York Yankees player Alex Rodriguez from 2017-2021.

J.Lo and Rodriguez also became engaged, though their wedding was postponed during the Covid-19 pandemic and eventually called off altogether.

Meanwhile, Affleck had a long-distance relationship with Lindsay Shookus from 2017-2018 before dating his Deep Water co-star Ana De Armas from 2020-2021.

Rekindled Romance

Affleck and Lopez were rumored to have started dating again in April 2021, 20 years after they first met.

J.Lo confirmed the reports that same July and revealed they had remained in contact after their breakup.

Unfortunately for their die-hard fans, the stars won’t divulge how exactly they got their second chance just yet – learning from their past mistakes and being more careful with what they share with the public.

“It’s not wise to share everything with the world,” Affleck told the Wall Street Journal.

“I just don’t want to be talking about my personal relationship in the newspaper. I’m going to exercise a little restraint. [But] I can say that it’s definitely beautiful to me.”

And Lopez told PEOPLE: “I feel so lucky and happy and proud to be with him. It’s a beautiful love story that we got a second chance.”

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A Happy Ending 

The couple officially got married in August 2022, later announcing the news on social media.

Skipping out on an elaborate wedding, Bennifer made it official with a runaway wedding in Las Vegas.

They later had a much bigger affair shortly afterwards with a second ceremony – a three-day party at Affleck’s estate in Riceboro, Georgia.

JLo had three gowns across the entire affair, and the pair have been sharing their romance a bit more broadly ever since, regularly posting sweet messages to each other online.

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