1. Ashton Kutcher and Brittany Murphy
2. Jared Leto and Cameron Diaz
3. Ryan Gosling and Sandra Bullock
4. Edward Norton and Salma Hayek
5. Kim Kardashian and Nick Cannon
6. Anne Hathaway and Topher Grace
7. Justin Timberlake and Alyssa Milano
The two had been rumored to have dated for a few months in 2002.
In Sept. 2013, Milano confirmed the long standing rumor of their brief relationship, saying, "Yeah that’s true, that was right after Britney broke his heart, I swooped in for the kill!"
8. Ryan Reynolds and Alanis Morissette
9. Moby and Natalie Portman
10. Orlando Bloom and Kate Bosworth
11. Wilmer Valderrama and Mandy Moore
12. Carson Daly and Tara Reid
13. Drew Barrymore and Tom Green
14. Scarlett Johansson and Josh Hartnett
15. Kirsten Dunst and Jake Gyllenhaal
16. Britney Spears and Colin Farrell
17. Mariah Carey and Luis Miguel
18. Naomi Watts and Heath Ledger
19. Rosario Dawson and Jay Z
The two reportedly dated in 2000, although neither have ever confirmed the relationship.