Byline: Jager Weatherby and Evan Rosen, New York Daily News, (TNS)
Britney Spears on February 7 shared a now-deleted Instagram post in which she claimed to have made out with Ben Affleck in the summer of 1999 — perhaps while she was dating Justin Timberlake.
The throwback photo — captured by TMZ before it was deleted — showed Spears, Affleck, and songwriter Diane Warren posing at a party, reportedly in June or July, celebrating the release of Spears’ debut album, …Baby One More Time, earlier that year.
“Cool pic of me and Ben Affleck and Diane Warren years ago!!! He’s such an amazing actor,” Spears, 42, captioned the post. “Did I fail to mention I made out with Ben that night … I honestly forgot … damn that’s crazy!!!”
“Wish I could tell you guys the story that happened before that!!! Oh dear, I’m just being a gossip girl,” Spears added, seeming to imply there were some juicy details to the story.
It’s unclear why the post was taken down so quickly, but it marked the first time Spears claimed anything of the sort occurred between the two. No mention of the makeout was made in Spears’ recently released memoir, The Woman in Me, in which she went into great detail about her past relationships.
There’s also been no word on the matter from Affleck, but if what Spears claims is true, the kiss would have occurred when she was 17 and Affleck was 26. There’s also the possibility they were both in relationships with other people at the time.
From 1997 to 2000, Affleck was in an on-and-off relationship with actress Gwyneth Paltrow, while Spears previously revealed Timberlake asked her out prior to the release of her debut album in January 1999.
The post comes in the wake of an ongoing feud between Spears and Timberlake, which has been brewing ever since she shared damaging details in her memoir released in October 2023.
Among those claims, Spears alleged she and Timberlake mutually cheated on each other during their relationship, which ended in 2002.
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