2. Mila Kunis and Macaulay Culkin
Not only were Mila Kunis and Macaulay Culkin and item, but they dated for 8 years!
Kunis and Culkin parted ways as friends before the actress traded up for Ashton Kutcher, who was also in an unlikely marriage with Demi Moore before marrying Kunis and having a baby girl.
Mila repeatedly voiced her concerns over settling down while she was with Culkin, which should have made it clear enough for everyone the pair wasn’t going to last.
Culkin and Kunis seemed like an unlikely couple mainly because Culkin’s star faded while Mila’s was on the rise. Culkin was once an insanely famous and sought-after child star, but his career took a turn for the worst when his parents started fighting over his personal fortune.
Mila, who saw great success with Black Swan following That ’70s Show, has settled down with Kutcher, and the two seem like a far more compatible match.