Naomi vuelve de sus vacaciones en St. Bart con muchas ganas de pasar tiempo con Liam, lo que les lleva a pasar una velada romantica en su nueva barca hecha por él. Adriana conoce a Gia Bond durante una reunión de Alcohólicos Anónimos y entablan una relación de soporte, que llega a más... Navid y Dixon quieren llevar a cabo un plan para separar a Jasper de Annie sin causar mucho revuelo. Dixon intenta retomar su relación con Silver, mientras ella esconde sus sentimientos para con Teddy. Harry y Debie acuden a una función escolar, dónde el encuentro con Kelly les lleva a entablar una pelea...

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.

Naomi finds out she can now access the money in her trust fund, so she decides to throw a giant birthday party where The Honey Brothers perform a few songs. Dixon, Navid and Liam decide to take Oscar out for a night on the town, but their party ends when Ivy finds a Facebook photo of Dixon doing a body shot off a girl. Annie has an instant connection with Charlie, a guy she meets at a coffee shop, but seems more interested in exploring her relationship opportunities with Liam. Jen is forced to go on bed rest until she delivers the baby and has no choice but to allow Ryan into her life. Silver confronts Teddy about his drinking problem.

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.