Ben Affleck, an Oscar-winning actor and director, is no stranger to high-profile relationships. His personal life has often made headlines, especially his relationships with some of Hollywood’s most famous women. After his recent split from Jennifer Lopez, the media has been buzzing with speculation about his romantic life. This article delves into his dating history, including his relationship with Lopez, his past marriages, and his rumored relationships after his divorce.
In August 2024, Ben Affleck and Jennifer Lopez officially called it quits after rekindling their romance in 2021. Their highly publicized relationship was marred by media attention from the start, leading to a rollercoaster ride for both stars.
Affleck and Lopez initially began dating in 2002, and after a highly publicized engagement, they called off their wedding in 2003. Despite their breakup, both stars found their way back to each other in 2021, reconnecting after Lopez’s split from Alex Rodriguez. The couple quickly became one of the most talked-about couples in Hollywood once again.
In April 2022, Affleck and Lopez became engaged for the second time, and in July 2022, they secretly married in a small ceremony in Las Vegas. They celebrated their love with a larger ceremony in Georgia that August. However, by May 2024, reports emerged about the couple’s marital struggles.
Affleck reportedly moved out of their shared home, purchasing a new property in July. By August 2024, the couple filed for divorce, officially ending their marriage after just over two years. Despite their separation, sources indicate that Affleck and Lopez have remained amicable, often seen together for the sake of their children.
Affleck’s Dating History Before Jennifer Lopez
Before his relationship with Jennifer Lopez, Affleck had several notable relationships, including two high-profile marriages. These past relationships have kept his love life in the media spotlight for decades.
Cheyenne Rothman: High School Sweetheart
Ben Affleck’s first significant relationship was with Cheyenne Rothman, his high school sweetheart. The two met at a summer camp in Vermont in 1990. They continued their relationship through their teenage years, even as Rothman attended a liberal arts college in Maine while Affleck pursued his acting career in California.
Rothman later moved to Los Angeles to be closer to Affleck, attending red-carpet events with him. They ended their relationship in 1997, shortly before Affleck’s next romance with Gwyneth Paltrow. Rothman later married and now lives a private life, far from the public eye.
Ben Affleck and Cheyenne Rothman (@benaffleckkofficial/Instagram)
Gwyneth Paltrow: A Brief Romance
Affleck’s next notable relationship was with actress Gwyneth Paltrow. They met in 1997 through Miramax and quickly became an item. By 1998, the couple was very much in the public eye, and their relationship grew despite challenges.
Paltrow hinted in interviews that Affleck wasn’t in the best place emotionally during their romance, which ultimately led to their split in 2000. Though their relationship was short, it was significant, with Paltrow later reflecting fondly on their time together, especially in regard to Affleck’s skills in the bedroom.
Ben Affleck and Gwyneth Paltrow (@benaffleckkofficial/Instagram)
Jennifer Lopez: The Relationship That Defined an Era
Ben Affleck and Jennifer Lopez’s relationship in the early 2000s is one of Hollywood’s most iconic. The two stars met in 2001 while filming their movie Gigli and quickly became one of the most talked-about couples in the media. They started dating in 2002, with Affleck proposing to Lopez later that year.
Their engagement became the subject of intense media scrutiny, which ultimately led them to call off their wedding in September 2003, just days before the ceremony was set to take place. Affleck later revealed that the media attention was so overwhelming that they even considered hiring decoy brides to avoid paparazzi.
After their breakup in 2004, Lopez reflected on their relationship in interviews, noting that she felt Ben was “the one” when they first met. Despite their separation, Lopez and Affleck have remained friends and have reunited romantically twice, first in 2021 and again in 2024, when they briefly married.
Ben Affleck and Jennifer Lopez (@benaffleckkofficial/Instagram)
Enza Sambataro: A Brief Relationship
After his breakup with Lopez, Affleck was briefly linked to Enza Sambataro, a TV ad sales executive from Boston. The couple’s relationship was short-lived and kept private. Sambataro later spoke to the press about how the intense media attention surrounding her relationship with Affleck was a major reason why she decided to step out of the limelight. She also mentioned that she preferred to have a private life rather than continue in a relationship under constant scrutiny.
Jennifer Garner: Marriage and Family
One of Ben Affleck’s most significant relationships was with actress Jennifer Garner. The two met in 2000 while filming Pearl Harbor, although they did not begin their romance until 2004 when both were single. Affleck and Garner married in 2005 in a quiet ceremony, and they went on to have three children together: Violet, Seraphina, and Samuel. Affleck often spoke highly of Garner, praising her role in providing stability in his life as he balanced his career with fatherhood.
However, the couple’s marriage was not without challenges. Affleck faced personal struggles, including rumors of infidelity and gambling, which led to their announcement of separation in 2015. Despite these issues, Affleck and Garner remained close, with Garner supporting Affleck through his recovery from alcohol addiction. Their divorce was finalized in 2017, but they have continued to co-parent their children amicably.
Ben Affleck and Jennifer Garner (@benaffleckkofficial/Instagram)
Lindsay Shookus: Public Relationship and Breakup
In 2017, Ben Affleck began dating Lindsay Shookus, a producer for Saturday Night Live. Their relationship was heavily covered by the media, with rumors suggesting that it may have begun during their respective marriages.
Shookus herself had been married and divorced before her relationship with Affleck. However, the couple faced significant challenges, including Affleck’s ongoing struggles with addiction. They broke up in 2019 after several reconciliations. Reports indicated that Shookus was frustrated with Affleck’s lack of progress in his personal life, especially as he relapsed into alcoholism.
Ben Affleck and Lindsay Shookus (@benaffleckkofficial/Instagram)
Shauna Sexton: A Brief Fling
In 2018, Affleck briefly dated Playboy model Shauna Sexton. The two were seen dining together in Malibu, and later, Sexton posted a photo of the two enjoying a trip to Montana. However, their relationship was short-lived, with Affleck eventually returning to rehab. Sexton later defended herself, dismissing accusations that she was responsible for Affleck’s struggles, stating that he made his own decisions regarding treatment.
Ben Affleck and Shauna Sexton (@benaffleckkofficial/Instagram)
Ana de Armas: A Short-Lived Romance
Affleck’s relationship with actress Ana de Armas, whom he met while filming Deep Water in 2019, was one of his most public romances in recent years. The two were spotted vacationing in Cuba and quickly became a media sensation. However, the relationship, which lasted from early 2020 to early 2021, ended when de Armas ended things.
In an interview, de Armas admitted that the intense media attention surrounding their relationship was a significant factor in their split. She also mentioned that the distance between them, as Affleck’s family was in Los Angeles and de Armas preferred to stay in Cuba, contributed to the relationship’s end.
Ben Affleck and Ana de Armas (@benaffleckkofficial/Instagram)
Current Status: Is Ben Affleck Dating Anyone?
After his divorce from Jennifer Lopez, Ben Affleck remains single, with no confirmed relationships. Although there were rumors that Affleck was dating Kick Kennedy, the daughter of Robert F. Kennedy Jr., these claims were quickly denied by Affleck’s representatives and Kennedy herself. At present, it seems that Affleck is focusing on his career and family life, particularly his three children with Jennifer Garner.
Ben Affleck’s dating history is marked by several high-profile relationships and tumultuous breakups. From his early romance with Cheyenne Rothman to his recent divorce from Jennifer Lopez, Affleck has navigated a complex love life under the public’s watchful eye. Despite his past relationships, he remains a dedicated father and continues to be a prominent figure in Hollywood. As of now, Affleck is single, and it remains to be seen what his next romantic chapter will look like.
