Ben Affleck is an Academy Award-winning actor, director, and screenwriter best known for Good Will Hunting, Argo, and playing ”Batman” in the DC Universe. Over the years, he has established himself as a major Hollywood player, both on-screen and off. But it’s not just his movies that people are watching, his personal life is often front-page news.
Ben’s romantic life has been anything but boring. From his early days with a high school sweetheart to messy Hollywood breakups and rekindled romances, his relationships have kept fans and tabloids talking. Whether it’s his obsession with women named Jennifer or infamous moments like that Ana de Armas cut-out, here’s a full breakdown of Ben’s dating timeline.
Ben Affleck and his teenage romance with Cheyenne Rothman
Cheyenne Rothman was Ben’s first real love, and they met at summer camp during their teenage years. Their sweet, long-term relationship lasted until 1997. She even supported him at the premiere of Chasing Amy. Though she stayed mostly out of the spotlight, Cheyenne played a big role in Ben’s early life and grounded beginnings. She was his high school sweetheart, but things between them ended for good.
Ben Affleck’s on-and-off again relationship with Gwyneth Paltrow
Ben and Gwyneth first met in the mid-’90s, but they started dating during their time filming Shakespeare in Love. Their chemistry was strong off-screen, and soon the two were making headlines with their romance. However, their relationship was an on-and-off affair, filled with public attention and some iconic red carpet appearances. Gwyneth later reflected that they weren’t well-suited for a long-term relationship. The couple broke up for good in 2000, but they remained on good terms afterwards.
Ben Affleck’s almost marriage to Jennifer Lopez
Ben met Jennifer on the set of Gigli, and their romance quickly became tabloid gold. He even starred in her Jenny from the Block video. The couple was deeply in love, and they got engaged in 2002. Ben had proposed with a massive pink diamond, which still remains among one of the most iconic celebrity engagement rings. But media pressure led them to call off their 2003 wedding. While the wedding was initially postponed by January 2004, Jennifer officially ended the relationship.
Ben Affleck and his marriage to Jennifer Garner
Ben and Jennifer Garner began dating in 2004 after connecting on the set of Daredevil. Their love story was straight out of a fairytale, and they married in 2005 and had three children together, Violet, Seraphina, and Samuel. Their marriage lasted for a decade, but rumours of cheating emerged in 2015, which led to their ultimate divorce. Despite their divorce being finalised in 2018, the pair remain close friends and co-parent their three kids together.
Ben Affleck and Lindsay Shookus
Ben started dating Saturday Night Live producer, Lindsay Shookus, in 2017. Their relationship was more private than his past ones, but still attracted media attention. The relationship ended shortly after, and it was reported that it ended due to Ben’s lack of commitment. They broke up in 2018, and insiders suggested the timing just wasn’t right for something serious between them.
Ben Affleck dated the Playboy model, Shauna Sexton
Shortly after splitting from Lindsay, Ben was seen out with Playboy model, Shauna Sexton. Their relationship was brief and casual, lasting only a couple of months. Sources close to Ben said he was focusing on sobriety, family, and work. While short-lived, the fling made headlines due to the timing and Ben’s public struggles.
Ben Affleck and his romance with Ana de Armas
Ben and Ana met on the set of Deep Water and were soon seen travelling and quarantining together. Their romance included PDA-filled walks and Ana temporarily moving in with him. However, differing goals, especially around starting a family, led to an ultimate split between them. Ben famously threw away a life-size cut-out of Ana after the breakup, adding to the drama and earning an unforgettable moment in pop culture history.
Ben Affleck and Jennifer Lopez rekindled their romance
In a plot twist no one saw coming, Ben and Jennifer rekindled their romance in 2021, nearly after two decades after breaking off their engagement. They got engaged for the second time and married in 2022, but things fell apart once again in 2024. J.Lo attended the Met Gala alone, speculation about their split rose, and among them, Ben moved out; she finally filed for divorce on their second anniversary.
Ben Affleck was linked to Kick Kennedy
Rumours swirled when Ben was spotted with Kick Kennedy, daughter of RFK Jr., in August 2024. The two were seen at multiple hotspots, but Ben’s rep denied any romantic connection. While some insiders claimed they were spending time together, others insisted there was no truth to these dating rumours at all.
Ben Affleck and Jennifer Garner are growing close again?
Despite being single, Ben has reportedly been getting flirty with Jennifer Garner again. Reports claim he would love a second chance with her, but she’s happily in a relationship with businessman, John Miller. While their co-parenting relationship remains strong, Jennifer isn’t interested in rekindling the romance, and Ben reportedly respects her boundaries. The two can be seen spending time with their three kids and prioritising their family and kids over any romantic feelings.
At the moment, Ben appears to be focusing on work and family rather than diving into another high-profile relationship. While it is being reported that he is casually dating, nothing serious has emerged for now. Whether he ends up back with one of his exes or finds new love is something only time will tell.
Ben Affleck has one of the most headline-worthy dating histories in Hollywood. With multiple Jennifers, a few unexpected flings, and some seriously viral moments, Ben’s dating life has been garnering headlines for decades.
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