The Hollywood couple that maybe could’ve been: Ben Affleck and Britney Spears.
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On Wednesday, Britney took to Instagram to share a throwback picture of herself, Ben, and Diane Warren — revealing in the caption that she and Ben apparently “made out” the night it was taken. 
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“Cool pic of me and Ben Affleck and Diane Warren years ago!!!” she wrote beneath the grainy black and white photo. “He’s such an amazing actor.” 
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“Did I fail to mention I made out with Ben that night … I honestly forgot,” she added, before teasing that she wished she could share “the story that happened before that.”
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“Oh dear, I’m just being a gossip girl,” she concluded, leaving fans guessing.
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It’s not entirely clear exactly when the picture was taken, however Ben’s facial hair indicates that it was perhaps around Summer 1999, when he was 26 turning 27, and Britney was soon to be 18.
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Around this time, Ben was a rising star in Hollywood fresh off the back of his first Oscar win for Good Will Hunting in 1998, which was the same year that Britney’s hit song “…Baby One More Time” shot her to super-stardom.
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So, if you’re a little confused by this new revelation, it’s worth mentioning that this is the first time we’re hearing about an alleged romance between Britney and Ben.
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Interestingly, Britney has since deleted the picture, and Ben has not addressed the popstar’s new claim. BuzzFeed has contacted Ben’s representative for comment.
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Of course, this wouldn’t be the first time Britney has dropped a bombshell about one of her past relationships. In her bestselling memoir, The Woman In Me, Britney spilled on her “passionate” fling with Colin Farrell in 2003.
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In the book — which was released in October 2023 — Britney described their brief relationship as “a two-week brawl,” recounting that they “were all over each other, grappling so passionately it was like [they] were in a street fight.”
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The pair actually took their relationship public at the time, making a giggly appearance at the premiere for Colin’s movie The Recruit — where he even denied that they were a couple when quizzed by red carpet reporters.
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However, Britney confessed in the memoir that she was still hung up over her 2002 split from Justin Timberlake around the time that she and Colin started seeing each other, so she tried to avoid getting “too attached” to the actor.
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“As I had before when I’d felt too attached to a man, I tried to convince myself in every way that it was not a big deal, that we were just having fun, that in this case I was vulnerable because I wasn’t over Justin yet,” she wrote.
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To add another layer to all this, Britney and Colin’s fling took place in the same year that Colin and Ben worked together on the movie Daredevil — along with Jennifer Garner, who Ben would marry only two years later.
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In a resurfaced TV clip from around the time Ben and Colin were promoting the movie, Ben actually teased Britney about her relationship with his costar, asking her via video message: “Did you call my boy Colin back, or what?”
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A flustered Britney then replied: “Well, I think girls shouldn’t call guys, I think guys should call girls. But don’t worry, Ben, he’s called, so it’s all good.”
