A sexist womanizer is killed by one of his former lovers and then reincarnated as a woman.
Steve Brooks is a sexist and the prototype macho. Unfortunately one day he is killed by one of his girlfriends. In heaven, though, there is no place for men like him and he is sent back to earth in the body of a woman so that he can see how women are treated by men like the one he once was.
- Steve Brooks (Perry King) is a chauvinistic womanizer with many enemies in the opposite sex. But one night, he is invited to a "surprise" party hosted by three of his ex-lovers. Unknown to Steve, the surprise is murder, and the three women attempt to drown Steve in a hot-tub. When the attempted drowning is unsuccessful, the ringleader of the three women, Margo (JoBeth Williams) shoots Steve in the chest with a revolver.
Steve enters a dark, empty place called Purgatory. God appears to Steve in the form of a bright pillar of light and represented by a male and female voice. The male and female personas of God tell Steve his treatment of women was repulsive and he is unfit to enter Heaven. To redeem himself, he must be sent back to earth to find just one female who truly loves Steve Brooks. Otherwise, his soul will be sent to Hell.
Steve wakes the next morning as his old self. The Devil (Bruce Payne) objects. He feels it is too easy for Steve to just charm another unsuspecting female, gaining entrance into Heaven without learning his lesson. In order to teach Steve a lesson and make it harder for him to accomplish his mission, the Devil recommends God change Steve into a woman. God agrees, and Steve Brooks becomes Amanda Brooks (Ellen Barkin). After getting over the initial shock of his/her new identity, Amanda goes to Margo's apartment to convince Margo that she is Steve. Amanda then forces Margo to give her lessons on being a woman. After struggling with putting on make-up, dealing with her hair, and walking in high heels, Amanda meets with Walter (Jimmy Smits), Steve's best friend. She tells Walter she is Steve's half sister and that Steve "decided to chuck it all and start again, like Gauguin". She also tells this to Steve's boss, Arnold (Tony Roberts) and convinces him (or blackmails him) to give her Steve's old job at the ad agency, with an increase in pay. As part of the deal, she promises to land the Faxton Cosmetics account, a company ran by Sheila Faxton (Lorraine Bracco). Sheila is a lesbian, so Amanda decides to use her new female body to seduce Sheila. Sheila becomes attracted to Amanda, and Amanda is excited about what would be a "truly unique sexual experience" for her. Unfortunately, she becomes extremely uncomfortable around Sheila. Margo explains to Amanda it is her homophobia that makes her uncomfortable around Sheila. Amanda eventually breaks up with Sheila, and tells Sheila she only came on to her to gain the account. Amanda does gain the account for the agency, but not before making yet another woman hate Steve/Amanda.
That night, Amanda prays to God for help. She is then visited by the Devil, who tries to get her to quit and become a recruiter for him. She refuses the Devil's temptation, and he goes away. The next day, Amanda calls the last of the women Steve knew. After several days trying to find one female who liked Steve, Amanda discovers, in fact, all hate him.
After a night of drinking and a bar-room brawl, Amanda carries an intoxicated Walter back to her apartment to spend the night. The next morning, Amanda is awaken when Margo comes by to visit. Amanda is in disgust and dismay when she discovers Walter had sex with her when she was unconscious. To the amusement of Margo, Amanda tells her she lost her virginity to Walter against her will. While Walter and Amanda are arguing, Margo hides the murder weapon in Amanda's sofa.
Steve's body is found in the river, and Amanda has to identify it. When she returns, she discovers her apartment has been ransacked by the police and they found the revolver in her sofa. Amanda is arrested and tried for Steve's murder (her own murder). She is found mentally unfit for the trial and sentenced to the State Mental Hospital. There, Amanda discovers she is pregnant with Walter's baby. When Walter comes to visit Amanda, she begins having complications with the pregnancy. After speaking with the doctor, Walter tells Amanda if she carries the child to full term, she may die. But Amanda is determined to have the baby because she feels God wants her to. She tells Walter the baby lives because she lives, and when she dies, a part of her will live on. Amanda asks Walter if he would be a full time father to the baby if she dies, and he agrees. She then reluctantly accepts Walter's marriage proposal. Throughout the wedding, Amanda giggles and smirks at the idea of marrying her best friend, and gives Walter a very awkward and quick kiss on the lips at the conclusion of the marriage ceremony.
Some time passes and Amanda goes into labor. With Walter beside her, she gives birth to a daughter, finding the only female in the world who truly loves her. She dies shortly after giving birth and goes to Heaven, where the soul of Steve/Amanda is unable to choose whether to become a male or female angel.
Five years later, Amanda remains undecided as she watches Walter and their child place flowers on her grave.