Running With Scissors is a memoir in which Augusten Burroughs recounts his unusual childhood after his mother sends him to live with her psychiatrist, Dr. Finch, at age twelve. There are few rules in the Finch household, and both Augusten and Dr. Finch's other children do mostly as they please, including smoking pot and having sex. At age thirteen, Augusten begins a sexual relationship with Finch's thirty-three-year-old son. Despite this unorthodox, and at times damaging, parenting method, Augusten comes to think of the Finches as his family.
Deirdre (Augusten’ mother) ends her affair with Fern and takes up with another of Dr. Finch’s patients. Dorothy is a young African American woman who paints her toenails in accordance with her mood and lives off the interest from her trust fund given to her by her father after he showed her his penis in a rowboat. She seems to be the odd Yang to Deirdre's Yin. She is unfazed by Deirdre's psychotic episodes and seems to crave more drama than even Deirdre can yield.
Dr. Finch has Deirdre hospitalized, and she returns with a man named Cesar Mendoza. Cesar is large, muscular and speaks with a Latin American accent. He was a patient at the retreat that Deirdre was committed to. He is married, with children and also wanted by the police. Dorothy is not upset by his presence, and he asks both of them to be his wives.
Augusten spends the night at his Mother’s apartment on the night she (and Cesar) return from the retreat, and Cesar attempts to have sex with him during his sleep, but leaves when an alarmed Augusten asks him to.
Augusten hears the sounds of moaning coming from the bedroom. Deirdre passes through the living room during the night and when Augusten asks her what she is doing, she informs him that Dorothy has never had sex with a man. Augusten hears what is obviously the deflowering of Dorothy.
The next day Dorothy and Deirdre tell Cesar to leave the apartment, sending him to live at Dr. Finch’s, where he begins to proposition Natalie. After agreeing to have sex with him for forty dollars, Natalie has her father kick him out of the house. He goes, but leaves all three women with yeast infections.