Winona Ryder
Winona Ryder is another beautiful Hollywood actress who has yet to walk down the aisle. She once dated Johnny Depp whose acting skill is no lesser than hers. They met in the filming of the Tim Burton film Edward Scissorhands. Winona was once involved in a theft scandal, having been accused and convicted of stealing a necklace from a famous and expensive jewelry shop. Fortunately, she has successfully reentered the entertainment industry in Stranger Things, a Netflix original. However, she has not found the same level of success yet in her love life.

Winona Ryder
Kourtney Kardashian
No American would not no the name Kourtney Kardashian. She became famous, along with her family, in a hit reality TV show. This famous celebrity experienced being in a long and troubled relationship when she dated Scott Disick. They have three children together, but their relationship did last as Disick had issues with drugs and fidelity (or lack thereof!). Kourtney has recently started dating Luka Sabbat, an actor. She is 19 years his senior. Kourtney may have been in several relationships, but someone has yet to put a ring on it.

Kourtney Kardashian