#40 – Macaulay Culkin & Mila Kunis
Easily the weirdest celebrity couple I have ever come across, Macaulay Culkin (little Kevin McCallister/Richie Rich who turned into a weird-looking hipster that my cats dislike) and Mila Kunis (the new Mrs. Ashton Kutcher and the cutest thing to ever come from Russia!) do not appear at first glance to be the type of people to fall in love. But that’s apparently how it was for the span of their decade long relationship.
To make this relationship even weirder: the two didn’t break up on bad terms. They continue to be great friends! At least they’re not like other Hollywood couples who have messy breakups and fight over the custody of children and/or cats. The only downside of their breakup was Macaulay’s downward spiral, which led him to turn to drugs to ease the pain—according to what he says.