Justin Timberlake, Sam Asghari & More

Justin Timberlake

Spears and her first known boyfriend in the industry, Justin Timberlake, confirmed their relationship in 1999, though dating rumors first emerged a year prior when they met while filming The Mickey Mouse Club.

The Oops! … I Did It Again singer told The Observer in 2001 that she had a deeper love with the boy band member than when she was younger.

“Like, we’ve gone through so much together and we’ve known each other since we were 12 years old,” she said. “We know each other inside and out.”

However, things turned sour when allegations that Spears cheated on Timberlake emerged, eventually leading to their split in 2002.