19 Kieran Culkin and Anna Paquin
If we knew back in 1990 that the Culkin brothers would be able to score Mila Kunis and Oscar winner Paquin, we’d lather our hands in aftershave and slap our cheeks in shock. But it’s true — in 2007, Culkin, star of Father of the Bride and Nowhere to Run dated the future True Blood star. Bloody unfair.