Ben Affleck's Love Story: Navigating Hollywood Romance from Gwyneth Paltrow to Jennifer Lopez and Beyond

Ben Affleck, a prominent figure in Hollywood known for his multifaceted career as an actor, writer, and director, has also captured significant public attention through his high-profile romantic relationships. His love life has often mirrored the dramatic arcs of his films, marked by deep connections, intense media scrutiny, and a unique journey of rekindled love. From his early sweetheart to his two marriages to A-list stars, Affleck's romantic history offers a compelling narrative of enduring affection and personal growth.

His romantic journey began in his formative years with Cheyenne Rothman. The two were high school sweethearts, meeting at a summer camp in the early 1990s. Their relationship lasted for approximately seven years, with Rothman even accompanying him to the premiere of Chasing Amy in 1997, before they eventually parted ways that summer.

Following his high school romance, Affleck entered a high-profile relationship with actress Gwyneth Paltrow. They began dating in 1997 after meeting through Harvey Weinstein and starring together in Shakespeare in Love. Their relationship was on-again, off-again for about three years, with Paltrow later remarking that Affleck was "not in a good place in his life to have a girlfriend" at the time. They ultimately split for good in October 2000, though they remained friendly over the years.

One of Affleck's most iconic relationships, and the one that coined the term "Bennifer," was with pop superstar Jennifer Lopez. They met on the set of their film Gigli in 2002, and their romance quickly escalated, leading to an engagement in November 2002. The couple became a media sensation, but the intense scrutiny led them to postpone their wedding just days before it was scheduled in September 2003.

“Due to the excessive media attention surrounding our wedding, we have decided to postpone the date,” they stated. “When we found ourselves seriously contemplating hiring three separate ‘decoy brides’ at three different locations, we realized that something was awry.”

Their engagement was officially called off in January 2004, with Lopez later reflecting that the media pressure "destroyed our relationship from the inside out." Despite the breakup, they remained on good terms.

Soon after, Affleck found love with actress Jennifer Garner, whom he had worked with on Pearl Harbor in 2000 and Daredevil in 2003. They began dating in 2004 and married in a private ceremony in Turks and Caicos in June 2005. During their marriage of ten years, they welcomed three children: Violet Anne (born 2005), Seraphina Rose Elizabeth (born 2009), and Samuel Garner (born 2012).

Affleck and Garner announced their separation in June 2015, a day after their 10th wedding anniversary. Their divorce was finalized in October 2018. Garner publicly supported Affleck through his struggles with alcohol addiction, even driving him to rehab in 2018. Affleck later called the divorce his "biggest regret," acknowledging his drinking played a role in their marital problems, but both maintained a strong co-parenting relationship and mutual respect.

In 2017, Affleck went public with his relationship with Saturday Night Live producer Lindsay Shookus. Their romance was on-again, off-again, with reports citing the challenges of a long-distance relationship and Affleck's focus on his sobriety. They initially split in August 2018 but briefly reconciled in early 2019, before ending things for good in April 2019.

During a brief break from Shookus in August 2018, Affleck was linked to Playboy model Shauna Sexton. Their fling was short-lived, lasting only a couple of months. Sources indicated it was a casual relationship, and Affleck's priority remained his sobriety and family, as he re-entered rehab shortly after they were spotted together.

From late 2019 to early 2021, Affleck dated actress Ana de Armas, his co-star in the film Deep Water. Their relationship became highly public during the COVID-19 pandemic lockdown, with paparazzi frequently capturing them on walks. They amicably split in January 2021, reportedly due to being at "different points in their lives," with de Armas not wanting to be based in Los Angeles where Affleck's children reside.

Remarkably, in May 2021, Affleck and Jennifer Lopez rekindled their romance, nearly two decades after their initial engagement ended. Their reunion, dubbed "Bennifer 2.0," quickly became a global sensation. They got engaged for a second time in April 2022 and eloped in Las Vegas in July 2022. A month later, they celebrated with a larger wedding ceremony at Affleck's estate in Georgia.

However, their second marriage faced challenges, and after months of speculation and living separately, Jennifer Lopez filed for divorce in August 2024. The divorce was finalized in January 2025. Lopez later reflected on the experience, stating she realized she would rather be single and focus on her own growth.

As of late 2024 and early 2025, reports have surfaced about Affleck's romantic life following his divorce from Lopez. In August 2024, there were unconfirmed rumors linking him to Kick Kennedy, daughter of Robert F. Kennedy Jr., though Affleck's representative denied any truth to the reports. Additionally, February 2025 saw speculation about a potential rekindling with ex-wife Jennifer Garner, but sources close to Garner indicated that while they maintain a strong co-parenting relationship, a romantic reunion was not mutual on her side. Ben Affleck is currently navigating a new chapter in his personal life, focusing on his children and career while remaining a prominent figure in the public eye.