In 1993, a studious and socially awkward teenager from Boise, Idaho, named Brandy Klark, achieves the remarkable honor of being her high school's valedictorian. Following her graduation ceremony, her best friends, Wendy (Sarah Steele) and Fiona, take her to a vibrant party where she experiences her first intoxicating moment. It is at this party that Brandy shares a fleeting kiss with the charming college student, Rusty Waters (Scott Porter), who has long been the object of her desire. Unfortunately, a misunderstanding occurs as Rusty confuses her for someone else. Devastated by this misperception, Brandy vows to explore the complexities of sexuality over the summer with the ambition to seduce Rusty and successfully complete her "To Do List" before the next academic year begins.
To accomplish this goal, Brandy secures a lifeguard position at the local pool, hoping it will bring her closer to Rusty while also allowing her to study along with Cameron Mitchell. Yet, her naivety and keen desire to impress lead her into a series of challenging scenarios. The laid-back staff, led by the enigmatic Willy, put Brandy through a series of initiation tasks that test her resolve. One such task involves cleaning what she suspects to be a prank involving feces, a misunderstanding inspired by the famous Baby Ruth joke from Caddyshack. To her utter shock, it’s not a prank at all, leading her to seek revenge by playfully pushing Willy into the pool, only to discover his own lack of swimming skills. To make amends, Brandy offers to teach him how to swim, marking the beginning of an unlikely friendship.
While navigating her summer journey, Brandy leans on guidance from her supportive sister Amber (Rachel Bilson), her mother, and her two friends. However, her conservative judge father grows increasingly uneasy about their candid discussions surrounding sexuality. Motivated by her ambitions, Brandy meticulously crafts a "to-do list" detailing various intimate experiences she aspires to explore throughout the summer. As she attempts to garner Rusty’s attention, she finds herself entangled in numerous encounters, particularly with Cameron, who starts developing genuine feelings for her. His excitement quickly turns to heartache when he discovers her list, realizing he has been nothing more than a stepping stone in her quest.
As summer progresses, the dynamics shift dramatically when Willy discovers Brandy and her friends indulging in some after-hours antics with a grunge band at the pool. The fallout is swift; Brandy finds herself sent home and faces the consequences of her actions when Cameron confronts her about her list, leading to a painful emotional breakdown.
In the wake of this turmoil, Brandy's friends, Wendy and Fiona, visit her only to stumble across her "scorecard" of sexual encounters. Shocked by her behavior and hurt that she prioritized her lust over camaraderie, they confront her, leaving in anger and branding her a "slut" for her lack of loyalty.
Despite these setbacks, Brandy’s connection with Rusty intensifies when they share a moment of rebellion at a rival pool, but their brief joy is cut short when Willy catches them, resulting in Brandy’s termination from her lifeguard position. Undeterred by the setbacks, she asks Rusty out, leading to a date that ultimately fails to meet their expectations, compounded by an awkward situation involving Brandy's parents.
The tension escalates as Willy arrives at Brandy's house, lip-locked by Amber's (Rachel Bilson) charms while unwittingly trying to separate her from Rusty. When Brandy and Rusty return, they are met with Cameron's rage, triggering a physical confrontation in which Brandy plays mediator.
Through this whirlwind of events, Brandy finally acknowledges the emotional damage her actions have inflicted on those around her, sharing heartfelt apologies and working towards mending her relationships. In a thoughtful gesture, she seeks out Wendy and Fiona for forgiveness, accompanying her heartfelt apologies with a poignant rendition of "Wind Beneath My Wings." This deeply emotional moment catalyzes their eventual reconciliation, rebuilding the bonds they once shared.
Brandy’s pivotal encounter with Willy at the pool further serves as a turning point when he offers her his job contingent on her return next summer, inspiring Brandy to find purpose amidst the chaos. But as time flies and the seasons shift, Brandy and Cameron find themselves back together at Georgetown University. Their reunion elicits a spectrum of emotions, and when they finally give in to their lingering desires, Brandy realizes one last dream. Just as she revels in this newfound intimacy, the reality of her father’s sudden interruption prompts her to confront the consequences of her choices, reminding her that every action comes with its price.
