Britney Spears Might Be the Only Person Who Made Out with Ben Affleck and Completely Forgot It Happened

The two apparently had a rendezvous shortly before she started dating Justin Timberlake.

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Britney Spears and Ben Affleck in 1999
(Image credit: Getty Images)

The list of people who would forget making out with Ben Affleck is probably pretty slim, but it includes at least one person: Britney Spears.

Spears went down memory lane on Instagram yesterday, sharing a black-and-white photo of herself with Affleck and songwriter Diane Warren in 1999. (Warren wrote hits like Celine Dion’s “Because You Loved Me,” Aerosmith’s “I Don’t Wanna Miss a Thing,” and Christina Aguilera’s “I Turn to You.” For Spears specifically, she wrote “When Your Eyes Say It” off of Spears’ 2000 album Oops!...I Did It Again.) 

Ben Affleck, Britney Spears, and Diane Warren in 1999

Affleck, Spears, and Warren, per Spears' Instagram

(Image credit: Britney Spears Instagram)

“Cool pic of me and Ben Affleck and Diane Warren years ago !!!” she wrote alongside the image. “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!!!”

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Spears’ rendezvous with Affleck, if our timelines are correct, happened just before she began dating Justin Timberlake, who she was in a relationship with from 1999 to 2002. Affleck, for his part, was off-and-on with girlfriend Gwyneth Paltrow from 1997 to 2000. 

Gwyneth Paltrow and Ben Affleck pose in the 1990s

Paltrow and Affleck dated off-and-on for three years, including the time period when he made out with Spears

(Image credit: Getty)

Gwyneth Paltrow and Ben Affleck pose in the 1990s

Paltrow later said of Affleck that he wasn't in a good place in his life to have a girlfriend at that time

(Image credit: Getty)

“Wish I could tell you guys the story that happened before that !!!” Spears continued on Instagram. “Oh dear, I’m just being a gossip girl !!! Psss I actually forgot !!”

Britney Spears and Justin Timberlake at the quot;Crossroadsquot; premiere.

Timberlake and Spears were the it couple at the turn of the century

(Image credit: Getty Images)

Spears and Timberlake sparked romance rumors in the spring of 1999, even though she told Rolling Stone at the time that she had “no feelings at all” for Timberlake and was laser-focused on her career. Of the same time period, Paltrow told Howard Stern in 2015 that Affleck “was not in a good place in his life to have a girlfriend.”

But a make out session with a pop princess—why not?

Rachel Burchfield
Rachel Burchfield
Senior Celebrity and Royals Editor

Rachel Burchfield is a writer, editor, and podcaster whose primary interests are fashion and beauty, society and culture, and, most especially, the British Royal Family and other royal families around the world. She serves as Marie Claire’s Senior Celebrity and Royals Editor and has also contributed to publications like Allure, Cosmopolitan, Elle, Glamour, Harper’s Bazaar, InStyle, People, Vanity Fair, Vogue, and W, among others. Before taking on her current role with Marie Claire, Rachel served as its Weekend Editor and later Royals Editor. She is the cohost of Podcast Royal, a show that was named a top five royal podcast by The New York Times. A voracious reader and lover of books, Rachel also hosts I’d Rather Be Reading, which spotlights the best current nonfiction books hitting the market and interviews the authors of them. Rachel frequently appears as a media commentator, and she or her work has appeared on outlets like NBC’s Today Show, ABC’s Good Morning America, CNN, and more.