Whoa — I know about some of these couples, but, still shocked about others.. I mean does anyone remember Alanis Morissette and Ryan Reynolds?! WHATTTTT?
1. Aaron Carter and Hilary Duff
2. Britney Spears and Justin Timberlake
3. Jessica Simpson and Nick Lachey
4. Ashlee Simpson and Ryan Cabrera
5. Ryan Gosling and Sandra Bullock
6. Alanis Morissette and Ryan Reynolds
7. Jennifer Lopez and Ben Affleck
8. Carson Daly and Tara Reid
9. Winona Ryder and Matt Damon
10. Mandy Moore and Wilmer Valderrama
11. Gwyneth Paltrow and Brad Pitt, who actually were a ’90s thing. Brad married Jennifer Aniston in 2000 . . . and started dating Angelina Jolie in 2005.