In a quintessential American high school setting, an artistic and sensitive teenager from the wrong side of the tracks harbors a crush on the most popular girl in school. Despite their differences in social standing, he is determined to win her heart. The young man, an outsider with a penchant for drawing, is befriended by a tomboyish girl who harbors her own secret love for him. As he confides in her and leans on her support, she aids him in his pursuit of the unattainable girl, all while dealing with her own emotional turmoil.

As the protagonist works on his ambitious plan to sweep the popular girl off her feet, he neglects the budding connection growing stronger by the day with his loyal friend. Meanwhile, the popular girl struggles with the pressures of her own social circle and is increasingly drawn to the sincerity and earnest affection of the boy from the lower social echelon. The protagonist's quest leads to a pivotal decision to spend his college fund on a perfect date in an effort to impress his crush, raising the stakes on his romantic gamble and testing the limits of friendship and true affection.