1/8
Frank Trapper/Corbis via Getty Images
Good Jeans
Spears and Timberlake dated between 1999 and 2002.
2/8
Jeff Vespa/WireImage
Pre-Grammys Party
The two attended Clive Davis' annual pre-Grammy Awards party at the Beverly Hills Hotel in 2002.
3/8
James Devaney/WireImage
Planet Hollywood Date
They hosted a Super Bowl fundraiser at the Planet Hollywood restaurant in Times Square in NYC in 2002.
4/8
D. Kambouris/WireImage
Album Release Party
Timberlake joined Spears at the release party for her album Britney in 2001.
5/8
Vince Bucci/Getty Images
Crossroads Premiere
The following year, he was her plus one at the premiere of her movie.
6/8
KMazur/WireImage
Shootin' Hoops
Spears was along for the ride when N*SYNC participated at a celebrity basketball game.
7/8
Kevin Mazur/WireImage
2000 MTV VMAs
All eyes were on them at music's biggest night.
8/8
Disney/Kobal/Shutterstock
M-I-C-K-E-Y...
A very young Spears and Timberlake appeared with All New Mickey Mouse Club co-stars such as Ryan Gosling and Christina Aguilera.