1. John F. Kennedy—Are You Kidding Me—Number Five
By the time Kennedy was with actress Angie Dickinson, the collection of Kennedy affairs littered the White House lawn like tattered flamingoes. This affair, unlike the other, Kennedy and his mistress kept quiet. In fact, this one remains mostly speculative as Dickinson will not confirm or admit to anything concrete. They had a relationship of some sort, but we all know what sort it was.