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Ben Affleck, the actor, director, and screenwriter, has long been in the public eye for both his career successes and tumultuous personal life. His relationships, often making headlines, have shaped much of his narrative, particularly his high-profile pairings with actresses and his recurring romantic entanglements. From his early love story with Cheyenne Rothman to his most recent marriage to Jennifer Lopez, Affleck’s romantic journey has been full of love, heartbreak, and reconnection.
A look at Ben Affleck’s high-profile relationships over the years-
1. Cheyenne Rothman: First love (1990 – 1997)
Ben Affleck’s first significant relationship was with Cheyenne Rothman, a woman he began dating while they were both in their late teens. The two met when they were students at the University of Vermont, and their love story continued through Affleck’s rise to fame in Hollywood. They dated for nearly seven years, from the early 1990s to 1997, before eventually parting ways. Affleck has described Rothman as a pivotal person in his life, and the two remain on good terms, though their relationship was largely kept out of the spotlight.
2. Gwyneth Paltrow: A high-profile romance (1997 – 2000)
Affleck’s relationship with actress Gwyneth Paltrow was one of the most talked-about celebrity relationships of the late 1990s. They met during the production of Shakespeare in Love (1998), where they became romantically involved. The relationship was intense and passionate, and the media often compared them to Hollywood’s golden couples. Their romance lasted for nearly three years, from 1997 to 2000, before the two parted ways. Despite the breakup, they remained friendly, and Paltrow even spoke about how Affleck was one of the great loves of her life in later interviews.
3. Jennifer Lopez: Bennifer (2002 – 2004, 2021 – 2024)
Ben Affleck’s relationship with Jennifer Lopez, famously known as “Bennifer,” remains one of Hollywood’s most iconic romances. The couple met in 2002 while filming Gigli, a movie that was critically panned but became a cultural talking point due to their chemistry. Their engagement in 2002, followed by a media frenzy, made them the center of attention for nearly two years. However, the couple called off their wedding in 2003, citing the overwhelming media pressure, and they split in 2004.
After nearly two decades of separate relationships, including high-profile marriages and engagements, Affleck and Lopez reignited their romance in 2021. The two had reportedly reconnected via email while Lopez was navigating her breakup with Alex Rodriguez. Their reunion quickly gained media attention, and in April 2022, they got engaged for the second time. In July 2022, they tied the knot in a modest ceremony in Las Vegas, and later that year, they celebrated lavishly in Georgia.
For a time, it seemed as though their love story had come full circle. Lopez described the wedding as a moment when “old wounds were healed,” and in a March 2023 interview, Affleck gushed about her brilliance, especially regarding her influence on fashion and culture. But, like many Hollywood marriages, their relationship faced its own set of struggles.
4. Enza Sambataro: A brief romance (2004)
After his breakup with Jennifer Lopez, Affleck briefly dated Enza Sambataro, a woman from his native Boston. Their relationship was short-lived, and not much is known about it, as the couple kept things private. It didn’t last long enough to garner media attention, but it marks a brief period in Affleck’s love life before he entered a more serious relationship with actress Jennifer Garner.
5. Jennifer Garner: Marriage, family, and divorce (2004 – 2015)
Ben Affleck’s most significant and longest relationship was with actress Jennifer Garner. The two met in 2000 during the filming of Pearl Harbor, but they didn’t begin dating until 2004. Their relationship flourished quickly, and they married in a private ceremony in the Caribbean in 2005. Over the next decade, they became one of Hollywood’s most beloved couples, raising three children together.
However, their marriage faced difficulties, with media reports suggesting that Affleck’s struggles with alcoholism and infidelity had taken a toll. They announced their separation in 2015, and their divorce was finalized in 2018. Despite the split, Affleck and Garner remained on amicable terms, co-parenting their children and publicly supporting each other’s endeavors.
6. Lindsay Shookus: A short-lived affair (2017 – 2019)
Affleck and Saturday Night Live producer Lindsay Shookus were briefly connected in 2017.Their romance was widely covered by the media, but it didn’t last long, with the couple parting ways in 2019. They dated for about two years, but their relationship was often strained by the pressures of their respective careers, with Affleck’s struggles with addiction and Shookus’s demanding job making it difficult to maintain the relationship.
7. Shauna Sexton: A brief flirtation (2018)
After his split from Shookus, Affleck had a brief fling with model Shauna Sexton in 2018. Their relationship was short-lived and mostly a subject of media gossip. It didn’t last beyond a few months, and the couple was rarely seen together.
8. Katie Cherry: A casual romance (2019)
In 2019, Affleck was rumored to be dating Playboy model Katie Cherry, though the relationship was never confirmed officially. Their romance was brief and didn’t capture much attention, as Affleck seemed to be focusing on his personal life and health at the time.
9. Ana de Armas: A love story that fizzled (2019 – 2021)
In 2019, Affleck began dating actress Ana de Armas after meeting on the set of Deep Water. Their relationship was marked by public outings and affection, and for a time, they were considered one of Hollywood’s hottest new couples. However, by January 2021, they had called it quits. Despite their breakup, both actors spoke fondly of each other, with de Armas reportedly continuing to be supportive of Affleck as he worked on his personal issues.
10. The final chapter: Jennifer Lopez revisited (2021 – 2024)
Ben Affleck’s reunion with Jennifer Lopez in 2021 marked the rekindling of one of the most famous love stories of the 2000s. After a brief engagement and public relationship in the early 2000s, the couple reconnected in 2021, just as Lopez’s engagement to Alex Rodriguez ended. Their second chance at love was met with both media enthusiasm and public curiosity.
Affleck and Lopez were married in a small Las Vegas ceremony in July 2022. However, reports surfaced in 2024 that the couple’s marriage had hit rough waters. As Lopez’s career commitments intensified, the couple’s dynamic reportedly shifted, and by May 2024, rumors of marital issues began circulating. By August 2024, it was reported that Affleck had moved out of their shared home and filed for divorce. The couple listed their separation date as April 26, 2024, marking the end of their whirlwind second marriage.
Ben Affleck’s romantic life has been filled with love, loss, and reconnection. His marriage to Jennifer Garner and his highly publicized second marriage to Jennifer Lopez demonstrate how personal growth and second chances can be part of the narrative. However, with recent reports of marital troubles, Affleck’s journey continues to evolve. It’s clear that his relationships, like his career, are always bound to capture the public’s imagination.