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Daily Mirror
Daily Mirror
Entertainment
Charlotte Hawes

Ben Affleck's drama-filled dating history – Ana de Armas to ex-turned-wife Jennifer Lopez

Ben Affleck has starred in popular movies including Justice League, He's Just Not That Into You and Pearl Harbour, but the Hollywood actor is also known for his drama-filled dating history.

The star, who recently tied the knot to Jennifer Lopez in a lavish ceremony, has had a turbulent time when it comes to past relationships, from calling off his initial engagement to Jennifer in 2002 to his marriage breakdown with another movie star.

As the Justice League actor turns 50, here's everything you need to know about his eventful relationship history.

Gwyneth Paltrow

Ben started dating Gwyneth Paltrow in 1997 after they met at a friend's dinner party.

The couple then went on to star in Shakespeare in Love and Bounce together, however, after three years of on and off dating, the pair decided to call it quits.

Ben Affleck and Gwyneth Paltrow dated for three years (WireImage)

At the time, Gwyneth told Primetime TV host Diane Sawyer: “I just think we have a very different sort of value system.

”Ben makes life tough for himself. He’s got a lot of complication, and you know, he really is a great guy. So I hope he sorts himself out.”

Jennifer Lopez 2002-2004

Jennifer Lopez and Ben Affleck initially dated for two years (Reuters)

Ben and popstar Jennifer Lopez began dating in 2002 after they crossed paths on the set of Gigli in late 2001.

At the time of their initial meeting, Jennifer was married to her second husband, dancer Chris Judd.

She filed for divorce in July 2002 and soon began dating Ben - with the couple adopting the name 'Bennifer'.

A few months later, Ben proposed to the singer but sadly, the couple called off the wedding just days before the nuptials were due to take place in September 2003.

In a statement, the couple said: "When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realised that something was awry.

“We began to feel that the spirit of what should have been the happiest day of our lives could be compromised. We felt what should have been a joyful and sacred day could be spoiled for us, our families and our friends.”

Just four months after postponing their wedding, Ben and Jennifer called off their engagement in January 2004.

Jennifer Garner

Ben Affleck and Jennifer Garner were married for 10 years (Getty Images)

Ben fell for Daredevil co-star Jennifer Garner shortly after his split from Jennifer Lopez.

The couple confirmed that they were dating in October 2004 and soon after, Ben got down on one knee and proposed to the 13 Going On 30 actress.

They tied the knot in June 2005 and welcomed their first daughter Violet in December of the same year.

The couple then went on to have two more children - Seraphina in January 2009 and Samuel in February 2012.

Soon after the couple celebrated their 10-year anniversary, they decided to call it quits and by October 2018, the couple were officially divorced.

In an interview with the New York Times in 2020, the actor said that divorce was one of his "biggest regrets".

He said: “The biggest regret of my life is this divorce.

“Shame is really toxic. There is no positive byproduct of shame. It’s just stewing in a toxic, hideous feeling of low self-worth and self-loathing."

Lindsay Shookus

Ben Affleck and Lindsay Shookus reportedly met on the set of SNL (GC Images)

Ben met Saturday Night Live producer Lindsay Shookus after his split from Jennifer Garner and the couple had a whirlwind romance.

Although it has never been confirmed, it is thought that Ben and Lindsay met on the set of SNL as the actor has hosted the show numerous times over the years.

The couple went public with their relationship in July 2017 and they dated on and off until April 2019.

Shauna Sexton

Ben Affleck and Shauna Sexton reportedly met in 2018 (Instagram)

The He's Just Not That Into You actor reportedly met model Shauna Sexton while he was on a break from Lindsay in August 2018.

However, the relationship was short-lived and they split just two months later.

Ana de Armas

Ben Affleck and Ana de Armas had a high profile romance (GC Images)

After months of speculation, Ben went public with actress Ana de Armas in 2020 a short while after the couple met on the set of Deepwater.

In March 2020, they were spotted kissing at an airport following a romantic getaway in Cuba.

Their 10-month relationship ended in January 2021, with a source telling People that "Ben is no longer dating Ana", claiming that their split was "completely amicable".

Following the split, Ana claimed that the media attention surrounding their relationship was "horrible" in an interview with Elle.

She added: "That’s one of the reasons why I left LA.”

Jennifer Lopez

Ben Affleck and Jennifer Lopez rekindled their relationship in 2021 (WireImage)

Following his split from Ana, Ben rekindled his relationship with former fiancée Jennifer Lopez in 2021.

A source told Us Magazine at the time that the exes have “always loved each other” and Jennifer's friends “won’t be surprised if they end up together”.

Another source claimed that the couple had a “heart-to-heart” following their respective splits from Ana de Armas and Alex Rodriguez in 2021, which “reignited a spark between them”.

In April 2022, Ben proposed to Jennifer for the second time, with the couple finally tying the knot in July 2022.

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