The Wild Claim Britney Spears Made About Her Past With Ben Affleck

Months after Britney Spears released her memoir, "The Woman In Me," she ran to social media to gift her fans another salacious detail from her eventful past. 

Unlike Spears' memoir, which mostly detailed the most heartbreaking revelations about her life and career, this update used an old photo featuring herself, composer Diane Warren, and Ben Affleck to fill in one gap in her famous dating history. "Cool pic of me and Ben Affleck and Diane Warren years ago!!!" Spears captioned the post, according to ET. "Did I fail to mention I made out with Ben that night ... I honestly forgot ... damn that's crazy!!!" Spears added before branding herself as a "gossip girl." Blake Lively would be proud!

Given the public's love of secret celebrity couples, Spears' admission prompted curious fans to do some digging about the photo's origin. According to Page Six, Spears and Affleck's make-out session took place in 1999 and may or may not have overlapped with the stars' respective relationships with Justin Timberlake and Gwyneth Paltrow. As the outlet detailed, the kiss possibly took place before Spears romanced Timberlake and likely during Affleck's on-again, off-again romance with Paltrow. Making matters even more scandalous and problematic, the New York Daily News reported that the alleged kiss would've happened in mid-1999, a few months before Spears turned 18. Affleck was in his mid-20s.

Britney Spears shared the story of her scandalous kiss with Ben Affleck nearly a quarter century after it supposedly took place. But if you thought that'd stop the paparazzi from bringing it up to the "Good Will Hunting" star, think again. 

In early February 2024, a paparazzo from TMZ crossed paths with Ben Affleck in Santa Monica and brought up the pop star's salacious claim. Unfortunately, Affleck didn't confirm or deny the supposed make-out session, but that doesn't mean he didn't respond. While the photographer caught Affleck in great spirits, his mood quickly shifted at the mention of Spears, which means he clearly wasn't in the mood to talk about her. As for why? Well, we may never know.

In a longer version of the encounter, after Affleck ignored the paparazzo's initial question asked in Spanish, he was caught emerging from his car with a young child, presumably one of his children with ex-wife Jennifer Garner. The paparazzo continued to make remarks from a distance, mentioning Spears at least once more in Spanish. Eventually, Affleck and the child moved away from the car and walked toward the photographer, who took a second chance to mention Spears. But like before, Affleck, who had a cup of coffee in his hand, refused to engage.

While Britney Spears doesn't give traditional press much of her time these days, she definitely gets her say out there by dropping random bombs of information through her Instagram account. While many fans are skeptical about the rumored make-out session between Spears and Affleck, if it even happened, others are all for the pop star spilling the details. "Britney just does not give a damn lol! She probably thinks this is a fun little story, but instead it's starting discourse," wrote one user on Reddit. Another fan wrote, "What happens in Hollywood does not stay in Hollywood." On X, formerly known as Twitter, a user encouraged Spears to share more details. "Tell us more girl," they tweeted.

Of course, there are some people who feel like Spears' admission was random and unnecessary, especially since she and Affleck, a.k.a. J.Lo's husband, have long moved on from whatever they may have shared in 1999. "That's not something you come up with after 20+ years. he's now a married man," tweeted one user. Another Reddit fan questioned whether or not Spears' account should be taken as gospel. "I'm just going to go ahead and suggest that Britney isn't the most reliable narrator know to history," they wrote. Meanwhile, another fan was waiting for Affleck's version of events. "Is there a Ben Affleck book I can read somewhere? I wanna know everything, lol," they posted to Reddit.