Britney Spears recently stirred the pot of Hollywood’s past romances by sharing a nostalgic photo featuring herself, Ben Affleck, and Diane Warren. The pop icon took to Instagram to post the throwback black and white image, intriguing fans with a caption that hinted at a forgotten romantic encounter with Affleck.
“Cool pic of me and Ben Affleck and Diane Warren years ago!!!” Spears captioned the image. She praised Affleck’s acting skills before dropping a bombshell revelation: “Did I fail to mention I made out with Ben that night … I honestly forgot,” she confessed, hinting at more untold stories from that evening with, “Oh dear, I’m just being a gossip girl.”
The timing of the photo, suggested by Affleck’s appearance, points to the summer of 1999. At this time, Affleck was enjoying his ascent in Hollywood following his Oscar win for “Good Will Hunting” in 1998, while Spears was catapulting to fame with her hit “…Baby One More Time.”
This is the first public mention of any romantic link between Spears and Affleck, adding a layer of intrigue to their well-documented public lives. The post has since been removed by Spears, and Affleck has yet to comment on the claim.
Spears is no stranger to revealing details about her past relationships. In her memoir, “The Woman In Me,” released in October 2023, she opened up about a “passionate” encounter with Colin Farrell in 2003, describing it as “a two-week brawl” filled with intense grappling. Despite their public display of affection at the premiere of “The Recruit,” Spears admitted to trying not to get “too attached” to Farrell, as she was still reeling from her breakup with Justin Timberlake in 2002.
Adding to the tangled web of relationships, Spears and Farrell’s fling occurred the same year Farrell and Affleck worked together on “Daredevil,” which also starred Jennifer Garner. Garner and Affleck would go on to marry in 2005.
During a press event, when asked about her stance on who should initiate contact in a relationship, Spears playfully responded, “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,” further fueling speculation about their interactions.
