Winona Ryder
Winona Ryder must be one of the most talented actresses in Hollywood right now. She used to be in a relationship with actor Johnny Depp, her costar in Edward Scissorhands. The actress suffered a lot of backlash when she got convicted of a shoplifting felony from a famous jewelry line. It was a good thing that she recently made a comeback by starring in Stranger Things! Even though her career has been rejuvenated, the same does not go for her love life.

Winona Ryder
Kourtney Kardashian
We are sure that you are familiar with Kourtney Kardashian. The famous reality TV show personality used to have a turbulent relationship with Scott Disick, who is the father of her kids. He had a hard time staying faithful to her and away from drugs. In the end, they decided to call it quits for good. She was recently rumored to be involved with actor Luka Sabbat, who is 19 years her junior!

Kourtney Kardashian