Matt Winkelmeyer/Getty Images Entertainment/Getty ImagesBen Affleck’s dating life has been a major point of pop culture interest for more than three decades. Ever since his early days as a ‘90s movie star, he’s been making headlines for his buzzy relationships with the most famous women in Hollywood. From Gwyneth Paltrow to Jennifer Lopez, Affleck’s roster of talented exes could easily fill an award show red carpet.There have been whirlwind engagements, two high-profile marriages, and a second-chance romance that took the internet by storm. All the while, Affleck has given fans meme-able tabloid pics (many with a cigarette and coffee in hand) that instantly became internet gold. These photos, combined with never-ending commentary about his love life, have made him an endless subject of media fascination for many years now.In recent years, the actor has kept his relationship status tightly under wraps, deflecting questions by saying dating is “not a big priority” at the moment. But for anyone who wants to do a deep dive on his history, there’s plenty to discover by combing through the archives. Read on for a comprehensive list of Affleck’s confirmed relationships and flings, going all the way back to his Good Will Hunting days.1990-1997: Cheyenne RothmanJeff Kravitz/FilmMagic, Inc/Getty ImagesAffleck met his high school sweetheart, Cheyenne Rothman, at summer camp in Vermont. The two dated until 1997, and their relationship was largely private. Rothman attended the premiere for Chasing Amy, one of Affleck’s first major films, marking their only public appearance together.1998-2000: Gwyneth PaltrowKevin.Mazur/WireImage/Getty ImagesAffleck and Paltrow met working on the film Shakespeare in Love, and dated on and off for two years, also co-starring in the romantic drama Bounce. 2002-2004: Jennifer LopezBauer-Griffin/GC Images/Getty ImagesAffleck and Lopez met on the set of Gigli, and reportedly got engaged within their first year of dating. (He memorably appeared in her “Jenny from the Block” music video.) They planned their wedding for September 2003, but postponed it due to “excessive media attention,” then ended their relationship altogether in early 2004. 2004-2015: Jennifer GarnerGeorge Pimentel/WireImage/Getty ImagesAffleck and Jennifer Garner shot Daredevil together in 2002, but didn’t start dating until two years later. He proposed in 2005, and the couple got married and welcomed their first child later that year. Affleck and Garner were married for a decade and had two more children together before divorcing in 2015.2017-2018: Lindsay ShookusGotham/GC Images/Getty ImagesAffleck met Lindsay Shookus on Saturday Night Live, where she was working as a producer. The duo made several public appearances together, including attending the US Open, before splitting in 2018.2018: Shauna SextonGabe Ginsberg/Getty Images Entertainment/Getty ImagesAffleck and Playboy model Shauna Sexton dated for a short time in 2018, traveling to Montana together for an outdoorsy vacation. They reportedly parted ways within a few months.2019-2021: Ana de ArmasBG020/Bauer-Griffin/GC Images/Getty ImagesAffleck and Ana de Armas worked on Deep Water together in 2019, and started dating later that year. They spent lockdown together and were frequently photographed taking their dogs for walks in Los Angeles, before splitting in early 2021.2021-2024: Jennifer LopezChristopher Polk/Golden Globes 2024/Getty Images Entertainment/Getty ImagesAffleck and Lopez shook the internet when they started spending time together again after his split from de Armas. They re-launched their relationship in July 2021, got engaged shortly after, and married in August 2022. The couple made plenty of red carpet appearances together before their breakup in 2024, which reportedly occurred due to a complicated mix of incompatibilities.
Ben Affleck’s Dating History, From Gwyneth Paltrow To Jennifer Lopez
