Plot

A disillusioned young writer living in New York City turns to drugs and drinking to block out bad memories and personal tragedy.

Jamie Conway (Michael J. Fox) is an aspiring writer and yuppie living in New York City who seeks oblivion in cocaine and the glittery nightclub scene as his life falls apart (his wife leaves him, his mother dies, etc.). With his hard-partying friend Tad Allagash (Kiefer Sutherland) tagging along with him during their nights out, Jamie finds it increasingly difficult to show up every day at his unfulfilling job as a fact checker for a literary Manhattan magazine.—Larry B.

Five days in the life of twenty-something Jamie Conway in New York City is presented. His brother Michael is urgently trying to reach him, but Jamie is doing whatever he can to avoid seeing Michael, let alone even talk to him. Jamie knows full well why Michael is trying to contact him at this point in time, the reason which is still too painful for Jamie with which to deal. Jamie is also dealing with his wife Amanda's abandonment, she an up and coming model who decided not to return to New York after a business trip to Paris, she, not having even talked to Jamie, working through a lawyer for divorce proceedings. These issues in combination have led to Jamie turning to drugs - specifically cocaine - alcohol and partying night after night with his friend Tad Allagash to cope. These coping mechanisms have in turn led to Jamie not being able to function in his day-to-day life, including at his job as a fact checker with a major magazine that prides itself on the factual accuracy of their articles. Jamie got into this work hoping eventually to transfer to the creative side of the magazine as a writer. But his career looks to be turning in the other direction as a moved up deadline by his boss Clara Tillinghast he believes is a tactic as grounds for dismissal if he does not complete the article satisfactorily by the deadline. Two other things that happen this week affect what happens to Jamie. First, Tad asks him as a favor to take out his cousin Vicky. And second, Amanda, without telling Jamie but which he discovers, returns to New York, he doing whatever he can to see her.—Huggo

After being abandoned by his wife, Amanda White (Phoebe Cates), aspiring fiction writer Jamie Conway (Michael J. Fox) drowns his sorrow by snorting cocaine and spends his weekends hopping between New York City clubs and drinking heavily. One morning, Jamie oversleeps, making him late for work at Gotham magazine, a small magazine company, where he struggles to maintain his job as a fact-checker in the non-fiction department. The incident provokes criticism from his boss, Clara Tillinghast (Frances Sternhagan), who warns that his job will be in jeopardy if he fails to deliver his next assignment before the end of the workday. Unable to focus, Jamie swallows a few painkillers before sneaking off to the bathroom to inhale a line of cocaine. He stays late to finish editing, but when his friend Tad Allagash (Kiefer Sutherland) invites him to a nightclub, he hastily skims over his work and returns home before going out. On his desk, he sees the piles of paper that represent his failed attempts to write a short story based on his relationship with Amanda. He considers typing a letter to his wife, but Tad arrives to pick him up.

At the club, Jamie and Tad meet two women who recognize Jamie as Amanda's husband, and ask about the status of their relationship. Jamie confesses they split up when she decided to pursue her modeling career in Paris, France. The next morning, a concerned co-worker and older woman named Megan (Swoosie Kurtz) calls to wake Jamie so he does not get into trouble again, but Clara calls in sick, so Jamie gets away with his tardiness.

As Jamie begins work on his next assignment, he strikes up a conversation with Alex Hardy (Jason Robarts Jr.), a drunken old fiction editor, who invites him out to lunch. Over several rounds of drinks, Alex encourages Jamie to pursue his writing and regales him with stories of his youth. Jamie eventually excuses himself, but on the way back to work, becomes fixated by a store mannequin modeled on Amanda's features. Noticing the label's designer, he deduces that Amanda must have returned from Paris and calls her modeling agency. After learning she will be working a fashion show in the city that Thursday, he begs Tad to use his connections to get him a ticket. Jamie agrees to entertain Tad's visiting cousin, Vicky (Tracey Pollan), so that Tad can go on a date with a Penthouse model.

When Jamie meets Vicky at a bookstore, they discover a mutual attraction. Out of habit, Jamie excuses himself to use the bathroom during dinner to snort more cocaine, but realizes he is having a nice time and decides to spend the rest of the evening sober. He kisses Vicky goodnight, and she gives him her phone number.

The next day at Gotham Magazine, Clara reviews the errors in Jamie's previous article and fires him. Megan is sympathetic, and suggests they have lunch together to talk things over.

That evening at Jamie's apartment, Tad answers a phone call from Jamie's younger brother, Michael (Charlie Schlatter). Although Jamie has been doggedly avoiding Michael for several weeks, he refuses to discuss why.

An evening or two later, Jamie attends the fashion show and sneaks toward the front of the runway. When Amanda emerges, he shouts her name and demands she explain why she left him. A security guard throws him out, and he returns to his apartment to find his brother, Michael, waiting on the front stoop. Unwilling to face him, Jamie runs in the other direction and jumps onto the next subway train, heading toward his former office. He hides until Clara leaves for the evening, and then apologizes to Megan for missing their scheduled lunch date. Instead, they have dinner at her apartment, where Megan asks about Amanda.

Drunk, Jamie recounts (in flashback) of meeting Amanda at a bar in Kansas City, Missouri, where he worked for the local newspaper. Attracted by his intellect and ambition, Amanda suggested they move to New York City where she could work toward being a fashion model. Within a few months, Amanda became worried that Jamie would gain fame and leave her, so she insisted they get married. However, she soon landed a modeling contract while Jamie struggled with his novel. Although Jamie believed they were still happy, Amanda abruptly ended their relationship over the telephone after taking a job in Paris.

When he finishes his story, Jamie takes two Valium from Megan's medicine cabinet and attempts to kiss her, but she rejects him. Embarrassed, he stumbles home and finds Michael sleeping in his bedroom. The boy reminds him that Friday marks the one-year anniversary of their mother's death from cancer, and requests that Jamie return home to help their father spread her ashes. Jamie admits that Amanda left him, and Michael wonders if he only committed to the relationship because it was their mother's dying wish to see her children married.

Jamie remembers his final conversation with his mother (Dianne Wiest) on her deathbed, but his reverie is interrupted by a phone call from Tad, who announces that he is at a party with Amanda. Jamie rushes to meet them, but is offended by Amanda's blasé attitude. He doubles over in a violent coughing fit and washes his face in the bathroom. Afterward, he telephones Tad's cousin Vicky, and tells her about his mother. Finally acknowledging his feelings, he begins to cry, and promises to call her back later. Without saying another word to Amanda, Jamie leaves the party and walks home alone. Passing a bakery, he trades his designer sunglasses for a baguette, and contentedly watches the sun rise over the city.