Winona Ryder
Winona Ryder is one of the show biz industry’s talented and gorgeous actresses. She and famous actor Johnny Depp once dated after they starred in Tim Burton’s film, Edward Scissorhands. Winona was caught up in a scandal after she was found guilty of shoplifting from a famous and luxurious jewelry boutique. The actress has now made a successful comeback with the hit Netflix series Stranger Things. Her love life is still waiting to come across the same success.

Winona Ryder
Leonardo DiCaprio
Despite having being in a relationship with model/actress girlfriend Camila Morrone for over four years, it came out this summer that the couple have decided to call it quits! It seems like Leo has a thing for girls in their lower twenties, and really just that. The Oscar winning actor has developed a trend of breaking up with women once they hit their mid-twenties, and everyone has really noticed. Previous romances include Gisele Bundchen and Bar Rafaeli, with both of these relationships ending before the women turned 25.

Leonardo DiCaprio