Set in the vibrant backdrop of New York City during the very early 1980s, two recent graduates from New Hampshire College, Alice Kinnon and Charlotte Pingress, find themselves struggling as underpaid readers at a publishing house. One evening, they gain access to an exclusive disco nightclub, where Alice hopes to connect with Jimmy Steinway (Mackenzie Astin), an advertising professional using the club to charm clients. However, tensions arise as Jimmy, irritable from being barred from inviting clients, ends up being expelled by his friend Des McGrath, the club manager facing job risks for allowing Jimmy inside.
After Jimmy's departure, Alice heeds Charlotte's suggestion and decides to leave the club with her second choice, Tom Platt (Robert Sean Leonard), leading them to his apartment for an intimate night. The next day at work, a discussion with coworkers about advancing in their careers compels Charlotte and Alice to consider sharing a rent with another girl, Holly (Tara Subkoff), given their financial limitations. They ultimately settle on a railroad-style apartment, despite Alice’s hesitations.
As their lives intertwine further, Alice becomes distressed to discover Charlotte's interest in Jimmy. Adding to her woes, Tom reveals that during their one-night encounter, he was still entangled with his long-term girlfriend, igniting feelings of betrayal in Alice. Meanwhile, Des starts to gravitate towards Alice.
Determined to earn the respect of her peers, Alice battles against the initial lack of support in her decision to champion a book about Buddhism suggested by Charlotte, who had previously dismissed the project. Despite the book's author not being whom he claimed, Alice stands her ground, stating that it is one of the best reads of her life. As Alice faces her challenges, Charlotte, now involved with Jimmy, wrestles with jealousy at the sight of their amicable rapport.
A dramatic moment surfaces at the club when Charlotte calls out Alice's health issue, revealing her diagnosis of gonorrhea. Although Charlotte later apologizes to Alice, her comment triggers unexpected interest from Des, resulting in the two casually dating. Tensions mount as Alice confronts Tom over her health concerns, leading to his admission of passing along herpes as well.
Amidst this tumult, Josh Neff (Matt Keeslar), a district attorney and acquaintance of Jimmy's, invites Alice to lunch under the pretense of discussing a book idea, but it quickly becomes evident he harbors romantic interest in her. Their date reveals more about Josh, who is combating manic depression. Upon her return home, Alice is met with the shocking news of Charlotte being rushed to the hospital for a miscarriage, and Jimmy's impending move to Barcelona for a new job opportunity.
Ultimately, both Alice and Charlotte are faced with the grim reality of layoffs following their publishing house's merger with a larger entity. Weeks later, the group finds themselves exiting an unemployment office with pink slips. Amid this emotional upheaval, Alice celebrates her newfound promotion after reclassifying her book project from nonfiction to self-help. While reflecting on their tumultuous experiences, Des and Charlotte ponder how their spirited personalities clash with the more reserved natures of Alice, Josh, and Jimmy.
As the subway ride concludes, Alice and Josh discuss prospects for the future, leading to a joyous moment as they abandon their character roles to dance to "Love Train," inviting the surrounding passengers to join in their celebration.
