Ben Affleck: Love, Breakups, And Hollywood'S Most Intriguing Romances

From High School Love Story to Hollywood's Spotlight

Ben Affleck’s love life has always been a hot topic, akin to the glitz and glam of a Hollywood premiere. Starting from his high school days in Cambridge, Affleck found romance with Cheyenne Rothman, a relationship that lasted for seven years. Rothman, who later carved her own path as a director, attended the 1997 premiere of Chasing Amy. The long-term couple broke up that summer, reportedly due to Rothman's desire for a life away from the Hollywood frenzy.

“She is the one who got away, but she’d had enough of Hollywood,” a source shared. “Perhaps he wouldn’t be so unhappy if they’d stayed together.”

After splitting from Rothman, Affleck stepped into the Hollywood dating scene with none other than Gwyneth Paltrow. Their relationship, sparked while filming Shakespeare in Love and Bounce, was on-and-off for around three years.

A Bennifer Love Story: The First Chapter

Ben Affleck’s headline-grabbing romance with Jennifer Lopez began in 2002 on the set of Gigli. They soon became one of the era's most talked-about couples and were even engaged before calling it off due to intense media scrutiny. After pursuing other relationships, including Affleck’s marriage to Jennifer Garner, the duo rekindled their romance in 2021.

The Garner Years and Personal Struggles

Affleck met Jennifer Garner on the set of Pearl Harbor and again in Daredevil. Their love story culminated with a 2005 wedding, leading to a decade-long marriage and three children. In 2015, the couple announced their separation, emphasizing their commitment to co-parenting. Affleck has been candid about how his struggles with alcohol impacted their relationship.

“I drank relatively normally for a long time. What happened was that I started drinking more and more when my marriage was falling apart,” Affleck shared with the New York Times.

Following their divorce, Affleck had notable relationships with Lindsay Shookus and Ana de Armas, both of which ended amicably. Shookus, a Saturday Night Live producer, and Affleck contended with their busy schedules, while de Armas and Affleck were reportedly at different points in their lives.

Full Circle with Jennifer Lopez

The world watched in awe as Affleck and Lopez rekindled their romance, culminating in a 2022 wedding in Las Vegas, followed by a grand celebration on Affleck's estate in Georgia. Their enduring love story is a testament to Hollywood's unpredictable nature, where the past often finds a way to collide with the present.