Sixteen-year-old Charles Cummings (Jon Cryer) is deeply passionate about photography, and one morning he sets up a shot on a San Francisco pier. His focus shifts abruptly when an arguing couple crosses his path. Frustrated, he reminds himself of his aversion to capturing people in his frames. Once they leave, he resumes his pursuit of the perfect shot of the harbor.
Upon arriving home, Charles meets Ken (Jeffrey Tambor), his mother’s newest boyfriend, leading to a sarcastic exchange. His mother, Joan Cummings (Ann Wedgeworth), encourages Charles to be more respectful to their guests. Later that evening, while developing his photographic negatives, Charles discovers a striking image of a woman—Laura Victor, played by Demi Moore—who was part of the couple's altercation. Captivated by her beauty, he prints large enlargements of her face to adorn his bedroom wall, but his attempts to identify her yield no results.
Charles’s older brother, Leonard (Peter Frechette), visits to introduce his fiancée, Susan (Elizabeth Daily), and invites Charles to join them in the North Beach district. Although underage, Charles uses Leonard's ID to sneak into a nightclub where he discovers Laura, the woman from the pier, performing as the lead singer of a band. He eagerly starts snapping photos of her, but a confrontation with the bouncer ends with him being escorted out, where he absorbs the name “Laura Victor.”
The next day, Charles is determined to see Laura again, slipping away to return to the club, where he witnesses her in another argument with her boyfriend, Scott (Scott Getlin). Amid their tumult, Laura convinces club owner Jake Lewis (George Wendt) to give her band another shot. Charles, hidden behind the bar, is captivated and decides to follow Laura when she leaves for an aquarium. He shares his photographs with her and offers to expand her portfolio, but she is too preoccupied with her own struggles to show interest.
Displaying his charm, Charles devises a plan to uplift Laura's spirits by taking party guests from Leonard’s bachelor celebration to watch her new band perform at Jake's club, preventing the venue from being empty. Subsequently, Laura pays a visit to Charles's high school, offering her gratitude and inviting him over for a photography session at her loft. As they spend time together, Charles brightens Laura’s gloomy mood by taking her on his scooter to iconic San Francisco locations for photos.
Eventually, however, hunger strikes, leaving them with just fifty cents. Disguised for the occasion, Laura leads Charles into a wedding reception to indulge in some free food. Their jovial spirits catch the attention of Gus Sosnowski (Hamilton Camp), the bride's father, who demands payment for their expenses or threatens to involve the authorities. Cleverly, Charles manages to convince Laura to perform for the guests, photographing her during a magical ballad that mesmerizes everyone, including Gus.
Afterward, Charles is even more impressed by Laura's talent and suggests she incorporate more popular songs into her setlist. However, once he drops her home, she is once again bereft about her career prospects and asks him to leave. In a moment of inspiration to aid Laura, Charles spends his savings intended for a photography career in Milan on advertising space across 150 taxi cabs to promote her image. Despite the enthusiastic reception from the public, Laura receives absurd inquiries regarding "escort services."
Upon confronting the reality of the situation, Laura is furious when she sees an ad showcasing her, alongside the message, "Laura Victor She's the Best! 555-1012." She pulls Charles from class, urging him to rectify the situation immediately. He attempts to explain his motivations, but she storms off in anger. Later, as she learns about the six thousand dollars Charles invested, she feels guilt for her outburst. In the meantime, he leaves her a heartfelt note to express his remorse.
In a twist of fate, that night, Jake visits Laura with a report detailing how Charles's campaign has sparked a surge in interest, ultimately leading to her re-hiring at the club. Thrilled, Laura agrees and performs to a packed house, capturing the attention of a record executive. However, amidst the celebration, she realizes that Charles is missing. Leaving a note for him, she is unaware that her brother has secured it for safekeeping.
At Leonard and Susan's wedding, Charles, as best man, discovers Laura's note tucked inside the ring box. Unable to contain his feelings, he interrupts the ceremony to reveal Laura's affections for him. Later that day, he rushes to her loft, where they share an emotional embrace, and she thanks him for paving the way to her record deal. Yet, when Laura mentions she must leave for Los Angeles the following day and terms him her "best friend," it sparks discontent within Charles. Hurt and confused, he reads her note aloud, which ends with "I love you," interpreting it as a sign of deeper feelings.
As emotions run high, Laura is taken aback by the misunderstanding. Just as Charles seeks a goodbye kiss, she surprises him further by beginning to undress. He calls his mother to announce that he won't be returning home that night. At the airport the following day, Laura reassures Charles about his future, stating that many women will adore him, sealing their experience with a passionate farewell kiss. Although he doubts he will love again, the journey with Laura has granted him renewed confidence, inspiring him to finally act on the affection from his classmate Mona.
