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Everything To Know About Ben Affleck's Dating History As Jennifer Lopez Files For Divorce; Find Out
Ben Affleck's love life has always intrigued fans, from high school sweethearts to A-list romances. Read on to dive into his flowery dating history as Jennifer Lopez files for divorce.
For quite a long time, the love life of Ben Affleck has been a public issue, from his high school sweetheart to high-profile relationships with leading ladies. Now, with Jennifer Lopez filing for divorce from Affleck, it is the perfect time to account for the complicated dating history that, in some ways, seems more like a whirlwind tour of celebrity romance.
Early 90s summer camp love: Cheyenne Rothman
Long before Ben Affleck was an A-lister in Hollywood, his first serious relationship was with Cheyenne Rothman. He reportedly began dating her while both attended Cambridge Rindge and Latin School in Massachusetts. They started dating after meeting at a summer camp in the early '90s when Affleck was just trying to get his career rolling. One such steadying influence during those heady days of celebrity was Rothman, who would herself go on to become a film director.
The pair famously walked the red carpet together at the 1997 premiere of Chasing Amy but ultimately broke up because of the stresses of Hollywood. While Affleck hoped to repair the relationship, Rothman chose a different path: one away from the spotlight.
Today, she is happily married and lives in California with her husband and their three teenage sons. She found fulfillment far from the glare of Hollywood.
The Gwyneth Paltrow era
After breaking up with Cheyenne Rothman, Ben Affleck proceeded to date another famous personality, Gwyneth Paltrow, in 1997. Their love quickly turned into hot news because they did two films together, Bounce and Shakespeare in Love, which made them one of the hottest couples in Hollywood.
Their relationship, however, was a rollercoaster, with the pair going through several breakups and reconciliations over three years. In years to come, however, Paltrow would indeed remember their relationship very fondly.
She told Howard Stern's show in 2015 that he was intelligent and talented but was not in the right headspace at that time for a committed relationship. Although the breakup was amicable and respectful, it clearly ended an era for both stars moving on to quite different paths.
Ben Affleck + Jennifer Lopez = The Bennifer
After his relationship with Paltrow, Ben Affleck met Jennifer Lopez on the Gigli set in 2001. At that time, Lopez was still married to her second husband, Cris Judd. It wasn't until her divorce was finalized in 2003 that they went public. The romance became a media sensation as quickly as it came, topping off with an engagement in November 2002 when Affleck proposed with a 6.1-carat pink diamond ring.
The much-anticipated marriage was soon drained by the immense media attention. In September 2003, just a few days before the wedding date, they called off the ceremony and cited excessive media attention as their reason. By January 2004, they had already broken up. Later, she remarked in her 2014 book, True Love, that it was her first big heartbreak.
A new chapter with Jennifer Garner
Close bonding and unspoken mutual support described Ben Affleck and Jennifer Garner in their romantic relationship, with a private life built around the family. They had first met on the set of Pearl Harbor in 2001 and again on the set of Daredevil in 2003.
This was a sparks-flying-all-over-the-place kind of meeting, considering that both were already attached to someone at that time. In April 2005, their whirlwind romance was sealed with a low-key engagement, and they became a married couple in June of the same year in an intimate ceremony in Turks and Caicos.
The couple had three children: Violet Anne, born in 2005; Seraphina Rose Elizabeth, born in 2009; and Samuel Garner, born in 2012. They celebrated their 10th anniversary and renewed their vows in a private ceremony but, claiming insurmountable differences, announced their divorce a decade later in 2015, stressing that they would put their offspring first.
Even after their split, Affleck and Garner were said to have been in close contact, with her offering substantial support during his battle with alcoholism. Affleck himself has talked about seriously having second thoughts on his divorce; he even called it "the biggest regret" of his life, though he would change his stance later on by stating to The Hollywood Reporter in 2023 that his struggles with alcoholism were his own fault. Although they ended up being in a divorce, they still respect and care for each other.
Lindsay Shookus and the struggles with busy schedules
Things only turned serious in 2017 with Lindsay Shookus, a producer for Saturday Night Live. The relationship was serious but got ruined due to the too-demanding schedules for both partners, which placed the relationship into an on-and-off situation. They broke up in 2019, one of the main reasons being their too-busy lives. Though the romance is now over, Shookus remains one of the prominent ladies on whom Affleck has dated.
Brief connection with Shauna Sexton
In 2018, Affleck briefly dated Shauna Sexton, a veterinary tech and former Playboy model. It only lasted some months, but he did have a big age gap with Sexton that added interest to their brief fling. The relationship came to an end without much fanfare, but it was one more piece of his personal life that kept the public interested in him.
Pandemic romance with Ana de Armas
Affleck and Ana de Armas's relationship began on the set of Deep Water, and after that, as has been said, became a media event. Probably the most visible period of their romance was during the pandemic when almost every day, photos would appear of them strolling about, fun-making in Los Angeles.
Despite happy public sightings, the relationship came to an end in January, reportedly due to differing life goals. Sources close to the situation revealed to Page Six that de Armas had been ready for more commitment, including having more children, which was way off track compared to what Affleck had in mind
The Return of Bennifer
Ben Affleck gravitated back to familiar territory once again by making his way back to Jennifer Lopez. It definitely was not a coincidence that about the same time, Lopez was dealing with the end of her engagement with Alex Rodriguez. An insider shared with E! News the two had kept in touch over the years. Several dinners ensued.
By May 2021, the two had taken a vacation to Montana, amazingly squeezed into their choked-full schedules by Affleck. As per E! News, sources close to Lopez describe her as being very impressed with how much Affleck had changed, terming him an 'evolved' version of the man she once loved.
Their relationship was very fast-paced, and by July, they were combining families at Universal Studios. With reports of a second engagement flying around since August, after being spotted browsing rings, it came to be confirmed nearly a year later by Lopez herself in her newsletter, On the JLo.
The two tied the knot in a private ceremony in Las Vegas in July, which Lopez spoke about in another newsletter issue. She described the experience as one full of so much love and so much heart strength, she even went as far as taking his last name to Affleck and showing off her wedding band in an Instagram story.
Armed with the renewed relationship, Lopez entered the studio to start work on This Is Me, Now, a sequel to 2002's album of the same name, one that documented their first romance.
Soon after, despite the fairytale comeback, the first cracks in their relationship began to show. The couple's low-profile appearance at a school play in May marked their first sighting together since March, with Lopez calling off her This Is Me. Live tour and further fanning rumors of trouble.
With the whispers growing louder, it became clear the reconciliation wasn't going to have a Hollywood ending after all. The final blow came when Lopez filed for divorce on August 20, citing April 26 as the official date of separation signaling the end of this era that kept millions of fans worldwide glued.
As Affleck now seeks to make sense of this latest chapter in his romantic life, his dating history has become a rich mix of high-profile relationships, public scrutiny, and personal growth. Each of these relationships has left its mark on him, shaping the narrative of one of Hollywood’s most talked-about figures.
ALSO READ: Throwback: When Jennifer Lopez Called Initial Split With Ben Affleck Her 'First Big Heartbreak'
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