Jane Austen
In a time where women were supposed to get married, have kids, and keep the house, Jane Austen did the opposite. She wrote about characters who had romantic relationships, but she never got married herself. She did get engaged at one point, but then called it off a few hours later.
Mindy Kaling
Mindy Kaling just recently had a baby... with herself. The successful actress wanted to have a kid but couldn't find the right person to have the kid with, so she went on her own! In one interview, she said, "In my 20s, I was not only boy crazy but marriage and relationship crazy... Now, it's almost the opposite."