In the vibrant summer of 1980 in Chicago, Illinois, we find Danny Martin (Rob Lowe), a charming restaurant supply salesman, deeply engrossed in a lively conversation with his exuberant and adventurous friend, Bernie Litko (James Belushi). Bernie's latest escapade involves a thrilling encounter with a mysterious woman in an apartment that created a scene worthy of curiosity: a flak suit, a tape recorder emitting the sounds of bombs, and gasoline splattered on the walls. Danny, itching to know about the woman’s profession, learns that Bernie left just before the firemen arrived, leading him to muse that "nobody has normal sex anymore."
As the sun shines above, the friends spend their day enjoying a friendly game of softball in the local park. Among the spectators is Debbie Sullivan (Demi Moore), an artistic director at an advertising firm, who, along with her friends, takes pleasure in picking out the most handsome players on the field. Following the game, they head to Mother's, a well-loved sports bar, where Debbie is disheartened to find out that her boss, Steve Carlson (Robin Thomas), opted not to join their post-game celebrations.
At Mother’s, as laughter and playful banter fills the air, Debbie, alongside her friend Joan (Elizabeth Perkins), watches the interaction between Bernie and Danny, who inadvertently draws Debbie's attention. After a brief introduction, Danny and Debbie retreat to his apartment, the evening taking a passionate turn as they relax to the sounds of his new stereo. However, in a moment of hesitation, Debbie decides against accepting a ride home, signaling a deeper longing that had begun to ignite within her.
Back at her cozy apartment, Debbie reveals to Joan that the rapid intimacy with Danny was fueled by an irresistible physical attraction. The next day at work, Bernie proudly shares tales of his amorous exploits, all while inquiring about Danny’s escapades. Danny describes his encounter with Debbie as merely "fun," but Bernie doesn’t let him off the hook easily, teasing him about his shy demeanor. Their playful camaraderie is soon interrupted by their boss, Mr. Favio (George DiCenzo), resulting in an amusing workplace dynamic.
As days pass, Danny reaches out to Debbie, who attempts to brush off their rendezvous, dismissing it as a mere fluke. Yet, unable to resist, she finds herself back at Mother's with Danny, leading to another night of intimacy and shared secrets, which solidifies their connection. Their relationship deepens as they indulge in delightful adventures – attending ballgames, enjoying leisurely lunches, and wandering hand-in-hand along the river, increasingly abandoning their work commitments.
With Debbie's burgeoning affection for Danny, her boss, Steve, begins to notice the signs of their romance and subtly expresses his interest in her. Concurrently, Joan attempts to check in on Debbie, but is left worried when she can’t reach her due to Danny's increased phone calls, which Bernie suggests might be overwhelming her. When Danny opens up to Debbie about his dream of owning a restaurant, the future appears bright, yet stress looms as work calls take a toll on their burgeoning romance.
As the complexities of their budding relationship unfold, Mr. Favio sets expectations for Danny that lead him to reconsider his commitments to both work and love. Meanwhile, tension arises as Debbie, feeling neglected, grapples with the challenge of balancing her new relationship while maintaining her professional responsibilities. In a moment devoid of understanding, they find themselves caught in arguments about issues big and small, including the expectations upon their living arrangements.
As the holiday season approaches, Thanksgiving dinner transforms into a battleground of unresolved emotions, culminating in a fierce debate about household responsibilities and the specter of past romances. The stress deepens further when, at the office holiday party, Debbie must fend off the lingering advances of Steve, only for Danny to observe the situation from afar, further igniting his insecurities about their relationship.
In a bittersweet reunion at Mother's on St. Patrick's Day, their paths cross once again, only to showcase their growing distance and the emotional fallout from their earlier separation. Danny’s realization that life without Debbie is unfulfilling leads him to a significant decision – he quits his job and takes the plunge, buying a diner he had always admired.
The story captures the ups and downs of love: misunderstandings, the quest for intimacy, and the relentless pursuit of happiness. When Debbie and Joan bike through the park, they exchange friendly banter and happen upon Danny, leading to apologies that illuminate the genuine love and regret that remain. As they plan to meet again, it becomes apparent that their bond, while tested, still may hold the promise of a brighter future together, skillfully weaving a tale of connection, heartbreak, and the hope of rekindled romance.
