After being left by his wife, Amanda White (Phoebe Cates), the aspiring writer Jamie Conway (Michael J. Fox) tries to cope with the heartache through heavy partying and substance use. His days turn into a blur of cocaine and nightlife as he bounces around New York City clubs. One fateful morning, Jamie awakens late for his job at Gotham magazine, a small publishing house where he's employed as a fact-checker in the non-fiction department. This slip-up leads to a stern warning from his boss, Clara Tillinghast (Frances Sternhagen), emphasizing that he needs to submit his next assignment by the end of the day, or else risk losing his position.
Desperate for focus, Jamie resorts to swallowing painkillers, quickly making the decision to sneak away to the bathroom for a line of cocaine. Even after hours of pushing himself to meet his deadline, he is easily swayed by his friend Tad Allagash (Kiefer Sutherland) to hit up a trendy nightclub. Before going out, Jamie glances at the numerous drafts of a short story he has written about Amanda, contemplating writing her a letter but ultimately leaving when Tad arrives.
At the club, Jamie and Tad run into two women who recognize him as Amanda's husband. They inquire about his relationship status, and Jamie shares their recent split—Amanda's choice to chase her modeling dreams in Paris had proved too much for their marriage. The next day, Megan (Swoosie Kurtz), a concerned co-worker, calls him to ensure he avoids trouble again, but luck is on his side as Clara falls ill, allowing Jamie to escape his tardiness.
As Jamie grapples with his work assignment, he meets Alex Hardy (portrayed by Jason Robarts Jr.), a seasoned and inebriated fiction editor who mentors him over lunch, encouraging him to pursue his writing dreams. However, Jamie finds his thoughts lingering on a mannequin that bears Amanda's likeness. His curiosity leads him to discover that she is back in town for a fashion show, prompting him to plea with Tad for a ticket. In a bid to keep Tad happy, Jamie agrees to entertain Tad's cousin, Vicky (Tracey Pollan), while he goes on a date with a model.
During an innocent outing with Vicky, sparks fly between them. But as old habits die hard, Jamie excuses himself to indulge in cocaine yet finds himself enjoying their time together enough to stay sober for the night, even sharing a kiss with Vicky, who leaves her phone number behind.
The following day brings troubling news—Clara fires Jamie after pointing out the many mistakes in his past work. Battling the aftermath of his dismissal, Jamie receives a call from his younger brother, Michael (Charlie Schlatter), with whom he has been avoiding communication about their family's struggles since their mother's death from cancer.
As he navigates through his chaotic emotions and past relationships, Jamie sneaks into a fashion show where he spots Amanda on the runway. He desperately calls out for her, demanding answers about their broken marriage, only to be forcibly removed by security. When he returns home, he finds Michael waiting for him. In a moment of vulnerability, Jamie shares with Michael about Amanda's departure, leading to a painful reflection on whether he had entered into the relationship to fulfill a promise to their mother.
The night spirals into a flashback of Jamie's fond memories of meeting Amanda in Kansas City, where her ambition and beauty drew him in. Yet, as Amanda chased her modeling career, Jamie struggled with his writing aspirations, culminating in a heart-wrenching phone call where she ended their relationship while she was in Paris.
In the days that follow, Jamie crosses paths with Megan, seeking comfort and connection. After drinking too much, he shares his past with her but is rejected when he attempts to kiss her, leaving him feeling lost. With Michael now at his apartment, Jamie seeks solace in his brother’s visit, as their mother’s death anniversary looms.
When he learns that Amanda is at a party with Tad, Jamie hurriedly goes there, only to feel downtrodden by her apparent indifference toward their past. Overwhelmed, he rushes home, trading his designer shades for a baguette at a bakery, finally allowing himself to process emotions he had long buried as dawn breaks over the city—a moment of clarity and acceptance.
