45.Mila Kunis and Macaulay Culkin

Mila Kunis and Macaulay Culkin are both child actors who entered the industry at a young age. They started dating in 2002, when Kunis was 18 and Culkin was 21. She was just starting her career, having just concluded her stint from That ‘70s Show, while he was a successful child star who tried to have a life outside of the limelight. According to Kunis, she and Culkin grew up together and became each other’s solace. Unfortunately, their relationship ended in 2011.

The actress recently admitted that it was a horrible breakup and she was the one at fault. She credits her immaturity and her lack of self-control for their nasty split while dismissing the cheating rumors. The two have sinced moved on and are now on good terms. Kunis is now married to Ashton Kutcher, with whom she has two kids, while Culkin recently welcomed his first child with actress Brenda Song.