Stanley Sweetheart is an aspiring filmmaker and a junior at Columbia University who recently moved to New York City from a wealthy California background. His father is dead, his relationship with his mother is distant, and his family is running short on money. He lives alone in a cramped Manhattan apartment on the Upper West Side, right across from a noisy construction site, with what feels like no real friends to lean on. Bored with lectures and hungry for a sexual outlet, he drifts into fantasies about a beautiful blonde classmate and, one night, stumbles into a local bar where a talkative hippie named Barbara has just reinvented herself as Shayne. A one-night stand with Barbara sparks a complication-filled connection, and Stanley’s eyes soon drift toward Barbara’s striking roommate, Andrea.
On campus, he eventually meets the classmate who has haunted his thoughts and begins to date Cathy. Cathy is sweet, earnest, and a virgin, and she initially rebuffs Stanley’s advances, leaving him frustrated. Over time, they fall in love and settle into a seemingly ordinary domestic rhythm, but Stanley’s restlessness returns. He finds himself fantasizing about Andrea again, even as Cathy’s concerns grow about the promiscuity surrounding her own living situation with her roommate Fran. To test the boundaries of his film-soaked world, Stanley invites Fran over under the guise of creating an underground movie called Masturbation. He drugs Fran slightly, films her in various sexual positions, and she masturbates in a bathtub—an act that culminates in Stanley and Fran having sex. The moment is fraught with guilt, yet Fran soon shows up when Cathy is away, pulling Stanley into an affair that he doesn’t know how to resist.
As the plot unfolds, Stanley drops out of college and accompanies Danny—an older, more sophisticated underground musician with a big appetite for this restless, creative life—to a psychedelic rock concert in a loft space. Danny and his circle, including Barbara and Andrea, drift into Stanley’s apartment, and the group’s hazy energy intensifies as they all smoke pot. The night becomes a turning point: Stanley finally speaks with Andrea, and the attraction he felt before intensifies. Cathy, meanwhile, finds herself drawn to Danny, creating a tangle of competing desires that strains every relationship.
Cathy ultimately ends the relationship, telling Stanley that they have not loved each other for a long time and that she wants to explore life with Danny instead. He drives her out of his life in a moment of anger, yet the absence of Cathy gnaws at him, and he searches for her in a way that reveals how deeply he’s entangled in the chaotic world he’s created. When he confronts Danny about Cathy, Danny admits he doesn’t truly care about Cathy, but he offers no real guidance or reassurance about stopping the drama.
The turn of events pushes Stanley toward Andrea’s apartment, where the mood remains electric and drug-fueled. They smoke together and, as the night deepens, Stanley and Andrea make love, joined later by Barbara. The trio shifts into a makeshift family dynamic, with Stanley playing “big daddy,” Andrea as “mama,” and Barbara as “little sister.” They inhabit this Greenwich Village micro-sphere of shared space, getting high, engaging in group sex, and exploring the margins of their unconventional bond. For a while, Stanley experiences a rare, intense happiness, but the thrill fades and his attention wanes again. When he encounters Cathy at another psychedelic event, he’s so high that he cannot respond to her attempts to reach him, leaving the audience with a haunting sense of the consequences of his lifestyle.
Tragically, Danny shoots himself behind his mother’s house, a stark and brutal consequence of the tangled web of desire and dependence. The morning after, Stanley wakes up at Andrea and Barbara’s apartment, choosing to go uptown to change his clothes. Andrea pleads with him to come back, insisting that she needs him. He promises he will return, but as he walks away, the ending remains deliberately unresolved: it’s unclear whether he will keep that promise or follow a different path, mirroring the uncertainty that has threaded through his entire journey.
