Here's a Juicy "Gossip" Britney Spears Revealed About Her Brief Fling with Actor Ben Affleck
Britney Spears has dropped the juiciest gossip about herself. The Oops!... I Did It Again singer revealed yet another bombshell secret on her Instagram account on Wednesday, February 7, 2024. The singer posted a black and white photo of herself with Ben Affleck and songwriter Diane Warren in 1999, and the caption said it all.
The 42-year-old wrote, "Cool pic of me and Ben Affleck and Diane Warren years ago. He's such an amazing actor. 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 !!! Pssst, I actually forgot." Spears has since made her social media private, per Page Six.
If the gossip is true, the singer's fling with Affleck must have been brief because, the same year, she began dating Justin Timberlake. The Gone Girl actor has yet to confirm the Toxic singer's "making out" claims. Meanwhile, Spears detailed her relationship with Timberlake in her tell-all memoir The Woman in Me.
The explosive book revealed a secret Spears kept hidden from the world- that she became pregnant with Timberlake's baby at the age of 19 and had an abortion. The excerpt read, "It was a surprise, but for me, it wasn't a tragedy. I loved Justin so much. I always expected us to have a family together one day," per PEOPLE.
"This would just be much earlier than I'd anticipated." She further wrote that while she was ready to become a mother, the Selfish singer wasn't ready for fatherhood. "But Justin definitely wasn't happy about the pregnancy. He said we weren't ready to have a baby in our lives, that we were way too young."
Meanwhile, Spears' tumultuous romantic life has plenty of hook-ups and break-ups. Among others, her high-profile whirlwind romance with Irish actor Colin Farrell has been described as a "two-week brawl" in her 2023 memoir. "Brawl is the only word for it — we were all over each other, grappling so passionately it was like we were in a street fight," the singer wrote.
The rumors were put to rest when Farrell took Spears as his date to the premiere of his film The Recruit. However, the Gimme More singer said she didn't take the relationship too seriously because she was still recovering from her break-up with Timberlake.
"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," claimed Spears. Meanwhile, Farrell also clarified, "We're not dating. She's a sweet, sweet girl. There's nothing going on — just mates."
Eventually, Spears married Kevin Federline in 2004 and gave birth to two sons- 18-year-old Sean Preston and 17-year-old Jayden James today. However, the marriage didn't last, and they broke up after three years, officially divorcing in 2007. She later went on to marry fitness trainer Sam Asghari in 2022 but reportedly split after 14 months in August 2023.
