In the bustling heart of New York City, we are introduced to Paul Hackett, a lonely and somewhat disenchanted computer word-processing consultant, portrayed by Griffin Dunne. Each day feels monotonously similar, marked by a routine of work, ungimmicked evenings of TV watching, and the occasional immersion into the pages of Arthur Miller. One fateful day at the office, Paul finds himself introducing a new trainee, Lloyd (played by Bronson Pinchot), into the world of computer operations. Left with an insatiable yearning for excitement in his life, Paul makes a daring decision to venture out.
His quest for connection leads him to a nearby coffee shop, where he encounters the enigmatic Marcy, played by Rosanna Arquette. Engaging in light banter, Paul manages to secure her phone number, setting off a chain reaction of unexpected events. With the clock ticking towards 11:32 p.m., Paul gathers the courage to call Marcy. She invites him to join her in SoHo, a seemingly innocent proposition that spirals him into an odyssey of eccentric encounters and bizarre circumstances.
As Paul leaps into a taxi, the ride turns chaotic as the burly driver speeds through the streets of New York at a staggering 80 mph, flinging money out the window and leaving Paul with no choice but to stiff the cabbie. Arriving at Marcy's loft, he is greeted by Kiki (played by Linda Fiorentino), an artist engrossed in her peculiar paper-mâché creation. An awkward encounter ensues, where Paul is pulled into a whirlwind of artistic chaos, resulting in his jacket being stained and a forced change of clothing.
Delighted to find Marcy again, they head to a diner where their conversation flutters from favorite films, particularly "The Wizard of Oz," to deeper matters of life and love, when suddenly the strange diner waiter announces that it's “on the house” due to the peculiar rules of late-night dining. As the night deepens, Paul and Marcy retreat to her bedroom, where the layers of Marcy’s complex character unravel, revealing an eccentric and troubled spirit. An ill-fated decision to smoke a joint leads Paul to act increasingly irritable, ultimately making him retreat from her as a rainstorm ensues outside.
Drenched and desperate, he discovers he lacks enough change for the subway fare and wrestles with a stubborn attendant at the station who refuses to bend the rules. Amidst his frustrations, Paul stumbles into an almost deserted bar where a note slipped by a waitress hints at her own dissatisfaction with life. Here, his request for cash is met with a bizarre favor: retrieving keys from the bartender’s apartment due to recent burglaries—a favor that showcases yet more absurdity in his quest.
In a frantic series of misadventures, Paul narrowly escapes a confrontation with two suspicious neighbors, retrieves Kiki's now-stolen paper-mâché sculpture, discovers Marcy's tragic fate, and finds himself thrust into darkness—inhabiting a world that seems to conspire against him. After a series of spine-chilling realizations and near-misses, including meeting a mysterious woman named Gail (Catherine O'Hara) who draws him back into the maelstrom, Paul begins to realize he's become the centerpiece of a vigilante search party.
As dawn approaches—illuminating a city that transforms with erratic energy—Paul's journey culminates in his unexpected return to his office, emerging from a night of chaos and bizarre encounters, just as the daily grind resumes. In a poignant closing moment, he sits at his desk, the memory of the night still vivid in his mind, as he reluctantly settles back into his gray life—an encapsulation of monotony that also seed-reveals the unpredictable nature of living life in the city that never sleeps.
