During the summer, most of the students at West Beverly were forced to attend summer school after Annie anonymously called the police to report Naomi's post-prom party. During the last weekend of Labor Day, Naomi, Silver and Adrianna hang out at the Beverly Hills Beach club. There, Adrianna runs into an old boyfriend named Teddy Montgomery, a tennis player and new student, while Naomi finds him irresistible. Navid also plans on spending his first romantic night with Adrianna, but jealousy gets in the way. Meanwhile, Annie has spent the summer isolating herself out of guilt for the hit-and-run accident that she committed, fearing that someone will discover her terrible secret.

The twisted Naomi continues her personal quest to destroy Annie's personal and professional life by spreading a false rumor about the existence of a nude photo of Annie, which causes a further divide between Annie and Dixon, as well as Annie's parents who continue to worry about her continuing slide down a dark path. Meanwhile, Liam decides to defy his stern and semi-abusive stepfather and try out with Dixon and Teddy for a spot on the school's surfing team. Elsewhere, Ryan worries about his romance with the manipulative Jen who begins to show off her true colors to him.

Teddy continues throwing his charm and weight around by inviting some of the gang to a day-long sailing trip on his father's yacht. There, more relationship troubles hit them. Dixon tries to move on from Silver by inviting over Sasha to whom he lies about his age to impress her. Navid begins to doubt about where his relationship with Adrianna is heading. Adrianna begins to show more appreciation to Teddy, while he continues to rebuff Naomi's further attempts at flirtation. Meanwhile, Annie, broken and humiliated from the nude photo of her that was posted to the entire student body, commits herself on a hell-bent mission to expose Naomi as the perpetrator. Both Harry and Debbie begin to worry about Annie's recent behavior and try to arrange a sit-down of talks with her. However this only stirs up more tension as Annie becomes more bellicose, refusing to talk to anyone. Harry then confides in Kelly about Annie's behavior - Kelly suspects that Annie's hiding something. Elsewhere, Liam is frustrated and disgusted at Annie and Naomi's continuing vicious feud. Neither one of them wants to associate with Liam anymore, so he confines himself to his garage where be begins working on a dark "project".

Dixon and Sasha continue their whirlwind romance despite his friends advice that he's moving too fast with it. That weekend, Dixon and Sasha drive up to Napa's Wind Country to sample some wine. But on the return trip, a flat tire leads to the discovery of a car trunk full of pornography, and a series of lies that Dixon makes up. Annie's new confident attitude quickly disappears when she realizes that Jasper, a new student at West Beverly, is nephew of the derelict that she hit on prom night. Navid assigns Silver and Gia to interview Jasper for a news piece about his uncle whom was a student at West Beverly, and who left behind a $100,000 inheritance to the school. Annie tries to befriend Jasper who confides in her about how his uncle lost everything, ending up homeless, and of Jasper's uncertainty with it all. Elsewhere, Navid continues to grow insanely and immaturely jealous over Adrianna's friendship with Teddy, with whom she confides about her uncertainty with Navid and of his envy. Elsewhere, Liam finally finds a way to get revenge on the psychopath Jen to make her reveal the truth to Naomi about her seducing him that night of the prom party when he discovers that Jen scammed a fortune out of a French husband that she married for money. But Jen has other ideas to slither out of the predicament she's in.

Both Kelly and Silver deal with the shocking news that their mother, Jackie, is dying of breast cancer. Kelly doesn't want to be sucked back into her mother's bad behavior which continues to persist, but Silver feels differently and wants to re-bond with Jackie. Meanwhile, Navid is devastated when Adrianna tells him that she needs time alone, but she turns to Teddy for attention. Jen continues to manipulate Naomi with her charming personality and manages to convince Naomi to lend her a large amount of cash which Jen plans to use to invest in a race horse. Elsewhere, Jasper rescues Annie from a bad date and the two become fast friends. Also, Harry, seeking to get away from problems at home, accompanies Ryan to a bar for some guy time and attempts to be his wing man when Ryan wants to move on from Jen.

The gang is preparing for the SAT's when Silver disagrees with Teddy's decision to skip college to focus on his tennis career and things grow even more tense when she meets his movie star father, Spence. As a result of falsely accusing her faculty adviser of sexual harassment, Naomi is now required to complete community service and publicly apologizes to her peers for the trouble she has caused. Meanwhile, Liam and his father, Finn, reconnect and attempt to rebuild their relationship as Liam moves in with him. Navid and Dixon host an underground gambling party that results in Dixon quickly becoming out of control with betting and he ends up owing Teddy's father's bookmaker, Mark, a lot of money. Debbie reveals to Harry that her yoga instructor made a pass at her, which forces the two to finally discuss their recent problems. Annie, aware of her parents marital troubles, turns to Liam for support. At the end, Naomi gets an unpleasant surprise when her psychotic and revenge-seeking sister, Jen, returns to Beverly Hills, with her French husband in tow, where they announce that they are the new owners of the Beverly Hills Beach Club.

Adrianna's new romance with pop star Javier continues to blossom, while Navid continues to work up enough courage to tell her how he feels. Jen has taken control of Naomi's finances and puts her on a tight budget, resulting in an instant meltdown by Naomi. Without her credit cards, Naomi is too distracted to realize Liam is in need of support to deal with the departure of his father, so he turns to Annie for comfort. Despite Spence's suggestion, Teddy refuses to end his relationship with Silver, and the two decide to spend the night together. Ivy invites Dixon to spend the summer in Australia with her and Laurel, but the idea doesn't go over well with his parents. Harry and Debbie's problems escalate when she finds out that Harry has been hiding Dixon's gambling issues from her. Meanwhile, Jasper returns to resolve things with Annie.

En el final de la segunda temporada, después de pasar tiempo con Liam y ver su valentía al confesar su robo a sus padres, Annie encuentra el valor para confesar a sus padres sobre su atropello y fuga. Jasper se pone celoso por la cercanía entre Liam y Annie y prende fuego al barco de Liam, lo que lleva a una pelea entre Liam y Jasper. Naomi revela secretamente a Ryan que el bebé de Jen es suyo, y Ryan, enfadado porque Jen no le permite estar en la vida del bebé, conduce borracho y arruina el letrero de la escuela. Dixon e Ivy atraviesan un momento difícil después de que él le cuenta sobre el beso con Silver, pero la verdadera decepción llega cuando descubre que no puede ir a Australia con ella. Adrianna y Navid tienen una reconciliación pública y Adrianna debe decidir si hacer una gira de un año con Javier. Silver decide dejar la decisión de si Teddy puede manejar una relación y una carrera de tenis en sus manos, pero se enfada cuando descubre que su padre intentó sobornar a Silver para que terminara la relación. El episodio termina con Naomi siendo aprovechada por un cierto profesor, y se da cuenta de la desesperación de la situación porque ya lo ha acusado falsamente de acoso antes.