1. Ryan Gosling & Rachel McAdams

2. Rihanna & Shia LaBeouf


Okay, so this one didn't last long, but it's still wild to think about. LaBeouf said in a 2009 interview that the couple lasted exactly one date. Could you imagine being a fly on the wall for that spectacle?
3. Jake Gyllenhaal & Reese Witherspoon

4. Lance Armstrong & Ashley Olsen


The pair hooked up for a bit right before Armstrong moved on to singer Sheryl Crow. 2007 was wild, y'all.
5. John Mayer & Jessica Simpson

6. Nick Cannon & Kim Kardashian

7. Kim Kardashian & Reggie Bush

8. Macaulay Culkin & Mila Kunis

9. Ryan Reynolds & Alanis Morissette

10. Scarlett Johansson & Josh Hartnett


Reports differ, but it looks like the relationship between these two lasted until early 2007. Remember how Hartnett was SUCH a thing at the time?
11. Ryan Reynolds & Scarlett Johansson

12. Evan Rachel Wood & Marilyn Manson

13. Britney Spears & Howie Day


2007 was bonkers insane. The pop superstar and the "Collide" singer reportedly linked up after meeting in rehab.
14. Ashanti & Nelly

15. Demi Moore & Ashton Kutcher

16. Michael Bublé & Emily Blunt

17. Lindsay Lohan & Samantha Ronson
