Al ver a Annie besándose con Ethan, Naomi decide tomarse la justicia por su mano y vengarse de Annie por haberla engañado. Los alumnos se quedan pasmados cuando se enteran de que Ryan se ha enrollado con una alumna, Kimberly, y de que ahora se ha pedido una baja. Kelly regresa tras su visita a Dylan y va a ver a Ryan para preguntarle si las acusaciones son ciertas.

Navid y Adrianna fantasean sobre su futuro. Cuando por fin les cuentan a los padres de Navid que han decidido pasar el resto de su vida juntos, estos no reaccionan como ellos esperaban. Silver y Dixon se adaptan al nuevo instituto de Silver, mientras los Wilson intentan adaptarse a tener a Naomi viviendo en su casa. Naomi convence a Annie para que salgan de dobles parejas con el amigo de Liam, pero la cita termina de una forma totalmente sorprendente. Cuando aparece su hermana mayor, Naomi no se imagina hasta qué punto Jen va a provocar un cataclismo en Beverly Hills.

Adrianna y Navid anuncian sus planes de boda a sus amigos, pero éstos no reaccionan como ellos esperaban. Para apoyar a sus amigos, Naomi, Annie y Silver organizan una fiesta de regalos para Adrianna, mientras Dixon, Ethan y Liam le organizan a Navid una despedida de soltero en un club de striptease. Ahora que ha vuelto a la ciudad la hermana mayor de Naomi, Jen, deciden vivir las dos juntas, y tratan de convencer a su escandaloso padre de que les permita recurrir al fondo de Naomi para mantener su lujoso estilo de vida. Ryan y Jen se encuentran por casualidad en el Peach Pit y mantienen una conversación llena de mentiras que los lleva a quedar para cenar juntos.

Liam, Dixon, and Ivy learn that Naomi and Jen will be attending a horse race to watch the racehorse that Jen bought with Naomi's money, and the three of them devise a crafty and very complex plan to finally reveal the truth to Naomi about her evil sister. Ryan also tags along with Jen to the races, and inadvertently learns how Jen acquired the racehorse used to win the race. Meanwhile, Annie and Jasper sneak out to go on a Saturday date even though Harry and Debbie have grounded her for her growing misanthropic attitude. Navid wakes up in the hospital after his "accident" with no memory of who pushed him down a flight of stairs. Adrianna visits Navid and following her conversation with him, makes a life-changing decision about her addiction to pills. Elsewhere, Silver and Teddy bond over the loss of both of their mothers and unexpectedly get close to each other.

Ryan encourages Naomi to press charges against Mr. Cannon and prepares himself for the consequences. Oscar decides to set his sights on Naomi and unknowingly helps her with the case against Mr. Cannon. Ivy decides to tell Dixon she slept with Oscar. Navid and Silver attend the Achievement Awards dinner while Annie, Teddy, Liam and Ian attend The Undies, an anti-achievement ceremony at the Beach Club.

Teddy begins to feel more comfortable in his own skin and decides to visit a bar in West Hollywood where he soon realizes he forgot his wallet and is forced to turn to Ian for help. Annie is ready to take her relationship with Charlie to the next level but is mortified when his friends catch a glimpse of her in lingerie. Now a single father, Ryan turns to Debbie for help and the two end up hooking up. Navid deals with the fallout of having turned his father in for employing underage girls in his pornography business by turning to Silver. Adrianna is oblivious to Navid's situation due to her new found fame.

Navid and Dixon convince a music producer to shoot a music video at Shirazi Studios. Adrianna's suspicions are confirmed, and she tells Silver about her plot for revenge. Emily distracts Annie and tries to get close to Liam, but her plan backfires. Teddy leans on Silver for support. Meanwhile, reality producers follow Adrianna and her friends around trying to shoot a pilot, and Naomi is surprised by her reaction to a nerdy lab partner who helps her out.