6. Shane West and Rachael Leigh CookPhoto: coolspotters.com
If one pairing could perfectly summarize our version of 90’s TV and movie heaven, it has to be this one. The E.R alum and She’s All That cutie spent two years together before splitting in 1999. They are such a gorgeous couple that it’s hard to believe they are no longer together. I wish their relationship worked, but unfortunately I can do nothing about it.