When Britney Spears Shared a Photo With Ben Affleck and Confessed to Making Out With Him

Pop princess Britney Spears once dropped a bombshell confession. She claimed she once shared a steamy 'make-out' session with actor Ben Affleck back in the late 90s! This surprising revelation came via an Instagram post that Spears quickly deleted. The post contained an old black-and-white photo from 1999. It showed a young Spears posing between Affleck and songwriter Diane Warren. In the caption, Spears reminisced about the snap, writing "Cool pic of me and Ben Affleck and Diane Warren years ago!!!" She then let the cat out of the bag by adding "Did I fail to mention I made out with Ben that night … I honestly forgot … damn that’s crazy!!!"

Spears went on to tease more juicy details saying, "Wish I could tell you guys the story that happened before that !!! Oh dear, I’m just being a gossip girl 🤓😏 !!! Psss I actually forgot 😏😉😂😂😂 !!" The Toxic singer clearly wanted to stir up some gossip, calling herself a "gossip girl". But she played coy, writing "Psss I actually forgot." The shocking Instagram confession was short-lived, however. Spears ended up deleting the whole post not long after sharing it. But screenshots had already spread like wildfire across the internet. The internet was set ablaze with speculation about what exactly went down between the young pop star and rising actor back in '99.

If Spears' claim is true, the make-out session would have occurred right around the time she started dating Justin Timberlake. The former *NSYNC member and Spears were an iconic young celebrity couple from 1999 until their bitter split in 2002. In her recent memoir, Spears alleged Timberlake cruelly dumped her via text message. As for Affleck, he was dating Gwyneth Paltrow on and off from 1997 to 2000. So the timing of his rumored fling with Spears lines up with that rocky relationship. Spears' Instagram tease has reignited long-standing rumors that she and Affleck hooked up at some point in the late 90s. There were whispers of a fling back then, with some fans speculating the pop star wrote Affleck's name on her hand for a music video as a subtle clue, as per Marca. However, no solid evidence of a romance ever emerged until the post.

The pop icon has been airing out plenty of personal details and secrets in her memoir The Woman in Me. She's opening up about her private life like never before after being freed from her 13-year conservatorship in 2021. When it comes to Affleck, his life is on a somewhat rocky path amid all the divorce rumors with Jennifer Lopez. Recently a source mentioned that Lopez has a 'plan to fix things' but warned that her desire to salvage the fairytale might lead to disappointment eventually. "She's always wearing rose-colored glasses! That's just who she is," as per The Sun.

This article originally appeared on 5.25.24