Mary-Louise Parker, Age 55 – Single

Even though Mary-Louise Parker is a mother of two, she has never actually been married. To be fair, she seems to have had incredibly bad luck when it came to choosing her partners, as one left her while she was pregnant, and the other one left before they got married.

She was in a relationship with Billy Crudup since 1996 but he apparently had an affair while she was pregnant, and left her for Claire Danes. Four years later, she met Jeffrey Dean Morgan on the Weeds set, they got engaged in 2008 only to break it off a little later. She’s now participating in a 2019 theatre production of The Sound Inside.