Lola "Lol" Williams leads an ordinary life in Chicago, sharing her world with her boyfriend Chad and a tight-knit circle of friends—Emily, Janice, and Kyle Ross. When they return to school after the summer, Lola learns that Chad has cheated on her, and the couple breaks up, setting off a chain of feelings and decisions that ripple through their group.
Lol and Kyle soon realize they have strong feelings for each other, a realization that comes with its own complications. Chad remains Kyle’s best friend, which makes pursuing something more with Lola delicate and tense. At the same time, Ashley, Lola’s nemesis, keeps flirting with Kyle, adding a layer of friction and rivalry to the evolving romance. Kyle’s musical ambitions, embodied in his band No Shampoo, face resistance from his father, who worries more about schoolwork than the risks and rewards of a budding musical path. Chad’s jealousy over Lola’s evolving relationship with Kyle intensifies the pressure, sharpening the drama within their social circle.
Meanwhile, Lola’s mother Anne, a divorcée, navigates her own tumultuous love life. She continues an on-and-off relationship with her ex-husband Allen, only to discover that he’s sleeping with someone else as well. This upheaval stretches the mother-daughter bond, and Lola senses that she and her mother are drifting apart. A party Lola throws becomes the flashpoint: Anne interrupts it and threatens to pull Lola from a class trip to Paris, leaving Lola grounded and frustrated.
Life takes a turn when Anne meets police officer James and begins dating him. James offers steady, practical advice about reconnecting with Lola, and Anne starts to take it. In the meantime, Lola attends a school presentation and, later, overhears voices in the girls’ bathroom—believing it to be Kyle and Ashley, she is unaware that the noise comes from Emily and Wen. The mistaken belief spurs a confrontation when Lola accuses Ashley of infidelity; Ashley does not deny the accusation because she relishes the discord and wants to drive a wedge between Lola and Kyle.
A major fight erupts between Lola and Kyle. Lola accuses Kyle of cheating, and the pair break up. Kyle’s lies about his grades and smoking pot lead to discipline from his father, who grounds him and destroys his guitar, amplifying the hurt. In a bid to spark Kyle’s jealousy, Lola briefly kisses her childhood friend Jeremy, attempting to elicit a reaction and test the strength of her feelings.
Meanwhile, Lola and her mother slowly begin to repair their relationship, and Anne agrees to let Lola go on the class trip to Paris. On the trip, Emily finally confesses the bathroom incident, admitting it was her and Wen, not Ashley and Kyle. With this truth out in the open, Lola and Kyle reconcile and share a tender night together, deepening their bond.
Returning home, the landscape of friendships shifts again. Chad and Kyle rekindle their friendship, and Chad even gives his blessing to Lola and Kyle’s relationship. Lola stands up for Ashley when Chad insults her, which helps Ashley and Chad become friends again. But Anne’s discovery of Lola’s diary—where Lola had written about sleeping with Kyle and smoking pot—sparks a fierce confrontation that pushes Lola to move out and live with her father.
Over time, Lola and Anne find a path back to each other, and Lola gradually moves back home. Kyle’s band triumphs in the battle of the bands, and his father finally begins to support his musical ambitions. Lola and Kyle stay together, while Ashley and Chad begin dating, and Emily and Wen acknowledge their relationship as well. The story closes with a warm, intimate moment: Anne and Lola laughing together, cuddling, and sharing a moment of renewed closeness as they look toward the future.
