Natasha Lyonne has to play a woman uncomfortable with the attention she gets from growing large natural breasts. Lyonne was given fake prosthetic breasts made out of silicone to play this part. At first, she was excited to play the part while wearing them. Then, director Tamara Jenkins told her to walk around for a day while wearing them. Lyonne came back and told Jenkins, "I get it now."
During filming, Natasha Lyonne was in a car accident on her way to the studio. She apparently hit the steering wheel so hard that she now has a noticeable scar on her chest. Production was shut for a few days before they shot the famous "vibrator scene" where she wears her nightgown pulled up to her neck to disguise the imprint of the steering wheel.
The film was going to be financed by the American Playhouse company but then it went out of business. The former head of Playhouse, Lindsay Law, became head of Fox Searchlight and was able to set this project up there.