Since she was a child, Natalie Miller (Patty Duke) has always thought she was an ugly ducking. When a boy called her "clown face", the six-year-old knocked out his front teeth with a shovel. Despite her mother's encouragement that she will grow up to be pretty, Natalie has never believed it will happen. When her parents bribe a young medical student to date her, Natalie discovers the ruse and moves out of her parent's house. She rents a Greenwich Village apartment from an eccentric landlady (Elsa Lanchester) and gets a job at the Topless Bottom Club. She rides a motorcycle to work, decorates her loft with a moose head, and rides up and down a dumbwaiter to get to her apartment. There Natalie meets David (James Farentino) an artist, and the two have a love affair before she discovers he is married. She considers returning home after finding him in bed with his wife. Al Pacino makes his first screen appearance in a minor role in this engaging drama.