Steve Brooks, portrayed by Perry King, is a self-centered womanizer surrounded by a long list of ex-lovers, each with their own grudges against him. One fateful evening, he finds himself invited to a seemingly harmless "surprise" party organized by three of these former flames. Unbeknownst to him, the true surprise is a plot for murder, with the women attempting to drown him in a hot tub. Their plan fails, leading Margo, played by JoBeth Williams, to escalate the situation by shooting Steve in the chest.
Following this shocking event, Steve enters a gloomy realm known as Purgatory. Here, he encounters God, depicted through a dazzling pillar of light and expressed with dual voices—one male and one female. They inform Steve that his exploitative behavior towards women has disqualified him from Heaven. To earn redemption, he must return to Earth and find just one woman who genuinely loves him, or else face eternal damnation.
Awakening the following morning, Steve discovers he has been transformed into a woman named Amanda, thanks to God's decision, supported by the Devil, played by Bruce Payne. This change is intended to teach Steve a lesson about the plight of women by making it more challenging for him to complete his task. After grappling with the initial shock of her new identity, Amanda seeks out Margo to persuade her that she is the former Steve. To navigate her new life, Amanda pressures Margo into providing her with lessons on femininity.
As Amanda struggles with makeup, hairstyling, and the challenge of high heels, she encounters Walter, portrayed by Jimmy Smits, Steve's loyal friend. Under the guise of being Steve's half-sister, Amanda deceives Walter, explaining that her "brother" has abandoned his old life to start anew, similar to Gauguin’s artistic journey. She cleverly manipulates Steve's boss, Arnold (Tony Roberts), into giving her Steve's former position at the advertising firm, promising to secure an important contract with Faxton Cosmetics—a company run by the charismatic Sheila Faxton (Lorraine Bracco).
Amanda quickly realizes that Sheila is a lesbian, giving her a unique opportunity to utilize her new identity in ways Steve never could. However, she soon finds herself uneasy around Sheila, prompting Margo to reveal Amanda's own homophobia. Ultimately, Amanda chooses to end her relationship with Sheila, confessing that she had only been attracted to her to land the business deal. Although Amanda succeeds in her corporate ambitions, she inadvertently earns yet another woman's disdain.
That night, Amanda seeks divine guidance, only to be visited by the persistent Devil, who tempts her to abandon her quest and become one of his recruits. Amanda stands her ground, rejecting temptation as she continues her search for any woman who might harbor feelings for Steve. Yet, as she reaches out to the last women from Steve's past, she discovers a harsh truth: all of them harbor contempt for him.
After a night marked by heavy drinking and a brawl, Amanda finds herself in a compromising situation with Walter, who ends up spending the night at her place. She later wakes to discover that they had a non-consensual encounter while she was unconscious, which leads to a heated argument. In the midst of this chaos, Margo sneaks the murder weapon into Amanda's possession, setting off a series of disastrous events.
When Steve's body is eventually retrieved from the river, Amanda must confront the reality of identifying her own corpse. Upon returning home, she finds her apartment ransacked by the police, who have discovered the weapon hidden in her sofa. This revelation results in her arrest and trial for murder, and ultimately, Amanda is deemed mentally unfit, leading to her commitment in a State Mental Hospital. Here, to her shock, she learns that she is pregnant with Walter’s child.
Despite the risks associated with carrying the baby to term, Amanda feels compelled to follow through, believing it to be God's will. She presses Walter to promise to be a dedicated father should she perish during childbirth, to which he agrees. In a moment of surrender, Amanda accepts his marriage proposal, albeit with a sense of humor, as she giggles awkwardly throughout the ceremony.
As time passes, Amanda goes into labor, with Walter at her side. She gives birth to a daughter, discovering the only female in the world who genuinely loves her. Tragically, she dies shortly after the delivery, ascending to Heaven where she faces the uncertainty of choosing to embody either a male or female angel.
Five years later, Amanda watches over Walter and their child as they tenderly lay flowers on her grave, still grappling with her identity in the afterlife.
