13 female celebrities who’ve dated below their league (With Pictures)

11. Mary-Kate Olsen – Olivier Sarkozy

The mere thought of Mary-Kate Olsen and the much-older Olivier Sarkozy makes many cringe. They are notoriously mismatched, both in age and looks. They first went public with their relationship in 2010, leaving the public scratching their heads. Not only is Mary-Kate far tinier and younger, she is also very obviously far more beautiful.

However, they announced that they were engaged in 2014, showing they could care less what others thought about them and their evident physical differences. Many have said they equate the way Mary-Kate and Olivier look together as a daughter and father, which is especially creepy and gives an even more awkward feel to the pair.