Ben Affleck’s Dating History: From Jennifer Garner To Jennifer Lopez

Ben Affleck has been a Hollywood heartthrob through and through with his love life always being the subject of much media speculation and today we are looking at his dating History. 

The actor-director has had his fair share of high-profile romances throughout his career, from his relationship with his Shakespeare in Love leading lady Gwyneth Paltrow to his marriage with his Daredevil co-star Jennifer Garner. 

However, Affleck’s longtime connection with his now-wife, Jennifer Lopez, has been one for the books. 

‘Benifer’ as they are popularly called began dating and got engaged in 2002, only to call off the wedding months later, gaining relentless media attention.

Affleck went ahead finding love in Garner. The two got married and welcomed three children before getting divorced in 2015. 

Six years later, after Affleck further dated the likes of A-lister Ana de Armas, he reconnected with Lopez and decided to give their love a second chance,

Affleck’s love life came back full circle when his long-awaited moment to say ‘I do’ with Lopez arrived in 2022.

Cut to May 2024 and the word around town is that the Hollywood sweethearts are going through a rough patch in their marriage again. 

With reports of divorce taking the internet by storm, we thought of taking a looking Ben Affleck’s relationship timeline with Lopez and in the process also deconstructing his dating history.

Ben Affleck’s dating history: Wives, relationships and ex-girlfriends

From having an iconic history of getting back with his exes to romancing some of the best women in Hollywood IRL, here’s breaking down Ben Affleck’s relationship history.

Cheyenne Rothman (1990 to 1997)

Ben Affleck e Cheyenne Rothman sono stati insieme per 7 anni. (1990-1997) andavano al liceo insieme.
Lei aveva 18 anni e lui 17.
Lei è del sagittario e lui del leone. pic.twitter.com/GLMIatbMWf

— Il draMMA di Giulia (@___livia95___) March 10, 2022

Before Ben Affleck made it big in Hollywood, he dated short-film director Cheyenne Rothman in the ‘90s. The two were high-school sweethearts and dated from 1990 to 1997. They attended Cambridge Rindge and Latin High School in Cambridge, Mass., together. 

The two first crossed paths while attending a summer camp and instantly got infatuated. Rothman even accompanied Affleck to the premiere of his movie Chasing Amy in 1997 but they split up by that summer. 

Affleck went on to become a star following the success of Good Will Hunting and Rothman went on to become a film director.

Gwyneth Paltrow (1997-2000) 

The next name to go down in Ben Affleck’s dating history is the Goop mogul, Gwyneth Paltrow. The two met in 1997 at a dinner hosted by Harvey Weinstein (film producer and convicted sex offender) and they hit it off. A year later in 1998, the two were cast in Shakespeare in Love, marking the beginning of their relationship. They were also spotted on the red carpet at a Golden Globes afterparty hosted by Miramax Films the same year.

But the nature of their relationship was pretty on and off. Looking back, Paltrow said the actor was not ready for a relationship. “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 okay with the two of us not being together,” she told Howard Stern on his SiriusXM radio show in 2018 as reported by People.

Affleck and Paltrow broke up by the end of 1998 — but it wasn’t the end of their relationship. Just a few months later, they were both cast in Bounce and sparked reconciliation rumours. While doing press for the film in June 1999, Affleck maintained that he was single, but in October, the duo was spotted kissing in Paris confirming that they had rekindled their romance. They continued dating for another year before finally calling it quits in October 2000.

However, Affleck and Paltrow have remained cordial throughout the years — with the latter even congratulating Affleck on his marriage to Lopez in 2022.

Jennifer Lopez (2002 to 2004 and 2021 to now)

 

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This has to be one of the most iconic Hollywood romances to go down in history. Affleck met Lopez on the set of their 2002 film Gigli while she was already married to celebrity choreographer Cris Judd. However, Lopez and Judd got divorced in June 2002 and she took no time in diving straight into a serious relationship with The Town actor.

The two were so madly in love that they got engaged just after a few months in November with Affleck proposing to Lopez with a pink diamond.

Their relationship became the talk of the town — the paparazzi loved them — and they earned the name ‘Bennifer’ during their romance. 

However, in September 2003, the power couple announced that they were postponing the wedding — just four days ahead of the D-day. “Due to the excessive media attention surrounding our wedding, we have decided to postpone the date,” they said in a statement. What followed was an announcement of the engagement being called off in January 2004. 

Reflecting on their break-up, years later, Lopez said the excessive media attention surrounding their relationship played a major role in their split.

“We were so in love, but also, there was this other thing happening where we were being criticised, and it really destroyed our relationship from the inside out because we were just too young to understand at that time what were really the most important things in life,” she told Rolling Stone in 2022.

Reconciliation 

Nearly two decades later, the Hollywood sweethearts reunited following Lopez’s split from her then-boyfriend Alex Rodriguez. They spent a weekend together in Montana in May 2021, making the speculations about their reconciliation rife. After the duo were spotted kissing at a gym during a romantic getaway to Miami, a source confirmed to US Weekly that they were back together.

“Ben and Jen feel so close to each other very quickly,” the insider shared, adding, “The old flame is absolutely rekindled. They picked up where they left off in terms of affection for each other.” 

Later that same July, the couple made things official with Lopez sharing a photo of the two kissing on her 52nd birthday. 

Talking about giving her romance with Affleck a second chance, Lopez told PEOPLE in February 2022, “I feel so lucky and happy and proud to be with him. It’s a beautiful love story that we got a second chance.”

Just two months later, ‘Bennifer’ were engaged again, with Lopez confirming that Affleck popped the question for the second time in her newsletter. In July, Affleck and Lopez officially tied the knot in a small, private ceremony in Las Vegas; Lopez called it the “best night ever.”

Next month, the couple celebrated their marriage with a larger ceremony at Affleck’s estate in Georgia which was followed by an Italian honeymoon.

Lopez also took Affleck’s last name.

Looking back at where they started and how it worked out, she expressed gratitude during an interview with Apple Music 1’s Zane Lowe in 2022, the excerpts from which were later published by People. “Once we called off that wedding 20 years ago, it was the biggest heartbreak of my life,” she said, adding, “Now, 20 years later, it does have a happy ending. It has the most would-never-happen-in-Hollywood ending.”

However, now in 2024, it seems that it isn’t a happy ending yet for Affleck and Lopez with rumours of divorce doing the rounds on the internet.

After not being spotted together for over a month, multiple sources confirmed that they were living separately. In May 2024, the couple were spotted arriving solo and briefly reuniting for his daughter Violet’s graduation party. Fans were quick to spot that it was unusual to witness Bennifer without their usual PDA.

Jennifer Lopez and Ben Affleck arriving at Jennifer Garner’s house for Violet’s graduation party. pic.twitter.com/c5CpRX9Vmg

— Bennifer Updates (@BenniferUpdates) May 30, 2024

However, an official statement about a possible divorce is yet to be released by the couple.

Jennifer Garner (2004 to 2015)

Next up we have another Jennifer, who also went on to become Ben Affleck’s wife and the mother of his three children.

Affleck and Garner first met on the sets of their 2000 film, Pearl Harbor, but remained professional as Garner was married to actor Scott Foley. They again collaborated for their 2003 film Daredevil and this was when they actually became good friends.

After Affleck and Garner split from their respective partners, the duo began corresponding over email — Garner later told Parade that Affleck was a “very persuasive writer.” 

In October 2004, the duo went public with their relationship at a World Series Game. Their relationship moved quickly, and on Garner’s birthday in April 2005, Affleck in his classic style, popped the question.

Two months later, the couple got married in a private ceremony in Turks and Caicos on 29 June 2005 and also confirmed that they were expecting their first child.

Affleck and Garner welcomed their daughter, Violet Anne Affleck, on 1 December 2005, followed by their second child, Seraphina Rose Elizabeth Affleck, on 6 January 2009. Three years later, their son Samuel Garner Affleck completed the family of five with his birth on 27 February 2012.

The couple kept a lowkey profile while raising their children and it all looked near-perfect from far afar. But at home, their marriage went through a fair share of challenges.

What followed next was a divorce announcement in June 2015. “After much thought and careful consideration, we have made the difficult decision to divorce,” the couple said in a joint statement, adding, “We go forward with love and friendship for one another and a commitment to co-parenting our children whose privacy we ask to be respected during this difficult time.”

Following the big split, Affleck and Garner shared joint custody of their three lovely children and continued to stay united for them. For the Gone Girl actor’s 43rd birthday, the entire family also took a trip to the Bahamas.  

In February 2016, Garner opened up about their divorce for the first time, in a Vanity Fair interview, she said, “He’s the love of my life. … He’s just a complicated guy.”

Even after their split, Garner supported Affleck as he entered treatment for alcohol addiction in March 2017. Once he was back from his 40-day rehab stay, the former couple officially filed for divorce.

About two years later, Affleck reflected on their marriage, calling their divorce “the biggest regret” of his life and acknowledged that his drinking played a role in his “marital problems” with Garner.

In 2021, Affleck further opened up about his divorce from Garner on The Howard Stern Show. The actor told Stern that part of the reason he started drinking was that he felt ‘trapped’ in an unhappy marriage. Days later, Affleck clarified his comments, saying that his words had been taken out of context on Jimmy Kimmel Live.

“I would never want my kids to think I would ever say a bad word about their mom. I had gone on and said how much we respect each other and cared about each other and cared about our kids and put them first,” he shared.

Today, Affleck and Garner are often seen hanging out together and spending time with their children. In fact, Garner is reportedly making a sincere effort to save Affleck’s marriage with Lopez.

Lindsay Shookus (2017 to 2019)

In the aftermath of his split from Jennifer Garner, Affleck found solace in Saturday Night Live producer and old friend Lindsay Shookus.

Affleck hosted the show in May 2013 when they both were still married. But the pair were spotted acting flirty at a movie premiere afterparty following his appearance on the show. In the following years, Affleck often visited Shookus at SNL a bunch of times.

But the rumours about their relationship gained momentum when Affleck and Shookus were spotted in London in June 2017. After this, the duo jetted back to L.A., where Shookus reportedly stayed at Affleck’s home.

The two dated for about a year with their relationship being marked by numerous paparazzi spottings in L.A. and New York City. As has been a pattern in Affleck’s previous relationships, they also vacationed in Maine, followed by another trip to Hawaii in 2018.

Shortly after, Shookus made her first comment about their high-profile relationship on Elle. She said, “It’s strange to me. My entire career has been behind the camera, and that’s definitely where I’m most comfortable. I’m a producer, I’m a mom, a friend. Being considered a public figure honestly makes me laugh.”

By 2018 summer, Affleck had met Shookus’ parents and the two were very happy to have each other in their lives. However, dating long-distance came with a set of challenges, and the couple broke up in August.

The word around town is that Affleck’s addiction played a major role in the split and it was then that he again turned to Garner for support.

He also dated Playboy model Shauna Sexton in between and later got back together with Shookus. The two officially started dating again in March 2019 but their romance didn’t last long the second time and they broke up again after a month.

Shauna Sexton (2018)

Model Shauna Sexton was a rebound for Affleck who had otherwise had serious relationships all his life. The two were spotted leaving Nobu restaurant together after his split with Shookus.

In the days that followed, Affleck and Sexton were seen on several occasions with the latter also being spotted spending time at Affleck’s home. 

But only after a few weeks of dating each other, Affleck entered rehab again for alcohol addiction — amid accusations that Sexton had gotten him thrown in rehab after drinking with the actor.

Sexton however denied the claims and continued visiting him at his treatment facility in Malibu, California. When Affleck completed treatment in October, they continued to date and even took a trip to Montana before calling it parting ways two days later. Perhaps, it was the closure trip that they needed.

Ana de Armas (2020 to 2021)

Actor Ana de Armas is one of the most recent names on the list of Ben Affleck’s dating History.

The two met on the sets of their film Deep Water (2022) in 2019 and instantly hit it off. After filming wrapped, things took a romantic turn for the co-stars.

By March 2020, they were seen spending time together in de Armas’ hometown of Havana, Cuba and the pair later took a vacation to Costa Rica where they were spotted taking a sunset stroll on the beach, confirming that they had become a thing.

What followed was a lockdown due to the COVID-19 pandemic and the couple quarantined together at Affleck’s home in LA. They were often seen on walks around the neighbourhood with their dogs acting all goofy and happy around each other.

In April 2020, the couple made their relationship Instagram official with photos (the picture with Affleck was later deleted from the post) of a desert getaway for de Armas’ 32nd birthday.

 

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The two apparently became very close on the vacation and Affleck reportedly wanted de Armas to get to know his children. Shortly after, photos surfaced of the couple spending time with his kids. The children also famously played a prank on their dad by leaving a cardboard cutout of de Armas on his lawn. A source told People that the couple and the children were ‘enjoying their time together.’

Later that year, de Armas joined Affleck, his mom and his kids on another vacation to Georgia, and she even gifted him a motorcycle for his 48th birthday.

In August 2021, the Blonde actress reportedly moved into Affleck’s home and they spent Thanksgiving with the Hollywood star’s children.

The couple had plans to take another holiday around New Year’s but they decided to part ways, amicably, before that could happen. Sources told People that they decided to take a break after almost a year together because they were at “different points in their lives.”

“She broke it off. Their relationship was complicated. Ana doesn’t want to be Los Angeles-based and Ben obviously has to since his kids live in Los Angeles,” the source told the entertainment portal. Another source added, “This is something that was mutual and something that is completely amicable.”

(Header and feature image courtesy: Instagram/Jennifer Lopez and IMDb/Bounce)

This story first appeared on Augustman Singapore

Frequently Asked Questions (FAQs)

– How old was JLo when she dated Ben Affleck?
Jennifer Lopez was in her mid-20s when she dated Ben Affleck in the early 2000s.

– How long did Ana de Armas and Ben Affleck date?
Ben Affleck and Ana de Armas dated from 2020 to 2021.

– When did Ben Affleck fall in love with Jennifer?
Ben Affleck has dated and been married to both Jennifer Lopez and Jennifer Garner, with the former in 2002 and again in 2021 and the latter in 2004. His marriage with Garner lasted for 10 years, from 2005 to 2015.