Ben Affleck’s dating history from JLo and Gwyneth Paltrow to Ana de Armas

27 August 2024, 17:06

With his marriage to Jennifer Lopez ending, we take a look back at Ben Affleck’s love life and dating history. From Gwyneth Paltrow and Jennifer Garner to Ana de Armas, here’s what we know.

With the amount the world has been obsessed with Ben Affleck’s love life, you’d be forgiven for assuming his dating history has been a little salacious.

But Ben appears to have always been the ultimate lover boy and ever since the ’80s has been in a long-term relationship after a long-term relationship, with several high-profile celebrities.

With his divorce from Jennifer Lopez making headlines, we take a look back and what could have been with some of his other exes.

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From Gwyneth Paltrow, and Jennifer Garner to Ana de Armas, here’s what we know about Ben’s relationship history.

Cheyenne Rothman - 1990 to 1997

Ben’s first documented relationship was with a woman named Cheyenne Rothman whilst the pair were still in high school.

The high school sweethearts went to Cambridge Rindge and Latin High School in Cambridge, Massachusetts and stayed together for almost seven years.

You can see how their similar interest in film helped Cheyenne and Ben stay together for so long because as Ben went off to be an A-list actor, Cheyenne had a brief stint as a film director, directing Release the Cracken in 2004.

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Gwyneth Paltrow - 1997 to 2000

Ben Affleck and Gwyneth Paltrow found each other quite quickly after his split from Cheyenne in 1997 and her split from Brad Pitt.

The two actors went on to star in Bounce (2000) and Shakespeare in Love (1998) after they began dating and their relationship lasted for three years, however, the pair were on and off again throughout that time.

Speaking to Howard Stern in 2015, Gwyneth revealed: "I think [my parents] appreciated how he’s super intelligent and he’s really, really talented and so funny, but he was not in a good place in his life to have a girlfriend. I think they were OK with the two of us not being together."

Jennifer Lopez - 2002 to 2004, 2021 - 2024

Ben and Jennifer Lopez’s love story spanned across two decades and began back in 2002 after the pair worked in Gigli together.

In the early 2000s, when celebrity relationships were all the rage, ‘Bennifer’ was born and their quick engagement, just a year after they began dating, had their fans bursting at the seams.

Unfortunately, due to all the wild media attention, the 2003 wedding was postponed and it seemed the couple couldn’t get back on track.

But 17 years later, the unimaginable happened, after marriage, kids, a divorce and some shorter-term relationships, it looked like like Ben felt Jennifer was the one that got away and in 2021 he began sending her love letters.

After going official on Jennifer’s 52nd birthday, the pair were cursed to repeat history with yet another swift engagement just seven months later.

In 2022, a decade after they originally planned to wed, the two finally got married in Vegas and then organised a bigger ceremony for their extended friends and family.

But unfortunately, the pair just aren't meant to be and by August of 2024, split rumours had been rife for a year and Jennifer filed for divorce.

Jennifer Garner - 2004 to 2015

After his first break up with Jennifer Lopez, Ben moved on quickly to yet another co-star having met Jennifer Garner whilst working together on Pearl Habour in 2001 and Daredevil in 2003.

The pair got married just a year after dating in 2005 and stayed together for over a decade, bringing three children into the world, Violet, Seraphina and Samuel.

The couple reportedly split because they had grown apart and the years of couple's therapy just wasn't enough.

Whilst the marriage officially ended in 2015, the couple’s divorce wasn’t finalised until 2018, by which time Ben had moved on with another woman.

Regardless of why it ended, the pair managed to stay good friends and co-parents to their children.

Lindsay Shookus - 2017 to 2019

Deviating away from the on-screen stars and taking a little time for himself after his public break up, Ben began dating Saturday Night Live producer Lindsay Shookus two years after his marriage ended and one year before his divorce was finalised.

With Lindsay used to working behind the cameras with big stars, the pair seemed like a good match.

Unfortunately by 2019, things had begun to fall apart and reportedly the relationship ended because the pair struggled with their busy lives and schedules.

Ana de Armas - 2020 to 2021

After a reported fling with Playboy model Shauna Sexton in 2018, Ben settled into a relationship with actress and Bond girl Ana de Armas.

The pair later starred in Deep Water together which premiered in 2022.

During the pandemic the couple were often papped taking walks with one another in LA, however, it wasn’t to last with the superstar couple breaking up just a year later in 2021.

Perhaps their 16-year age difference had something to do with it as sources told Page Six they had broken up because they were at “different places” in their lives.

According to the source: "He [Ben] would not commit to having more kids… She is in her 30s. It was a deal-breaker."

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