Miley doesn't like her new room, but doesn't know how to tell her dad. Meanwhile, Jackson puts up with the annoying neighbor TJ to get close to TJ's cute cousin Siena.
Miley is contemplating moving back home to Tennessee but Robby has a surprise for her.
When Robby brings Miley's horse "Old Blue Jeans" out to surprise her, Miley realizes just how home sick Blue Jeans is without enough land to roam on.
When Lilly's mom gets a job in Atlanta, Lilly fears that she will not be able to finish her schooling with her friends in Malibu.
When Lilly loses her new job at the mall, Miley helps her out by suggesting she become the Stewart housekeeper. When Lilly's overzealousness to keep things spotless drives she and Jackson crazy, they devise a plan to get Lilly her old job back.
When Hannah gets a part in an animation film guest starring the best voice over actor in the biz, she ultimately gets fired by the director because her skill level is not up to par.
Miley tries to return home from a Hannah concert in time to celebrate Lilly's birthday but a series of unfortunate events, prevents her from arriving on time. At home Jackson goes to a Laker game and ends up taking Lilly with him to help celebrate.
When Hannah serves as a judge in a singing competition, she is surprised and happy to vote for Oliver who ends up going to the next round. But when the success starts to turn Oliver into a bit of a jerk, Miley must decide whether to continue to vote him.
Miley and Lilly mistakenly believe that Oliver has a crush on the school nurse. When they instead learn that Oliver is secretly dealing with the news of being diabetic, the girls work overtime to keep him away from all things sweet.
When Mamaw drives her old Cadillac cross country for a visit, the Stewarts decide that it's time to get her a new one. After it's been junked, Miley discovers Mamaw's emotional attachment to the car and they must find a way to recreate the car.
Miley thinks that Jackson is responsible for revealing that Hannah sucks her thumb so she ruins one of his dates as payback.
When Miley gets injured at a Hannah concert and has knee surgery, she receives several visitors in the hospital including Oliver who she hears say "I love you" while half asleep.
While aboard the S.S. Tipton Miley loses both the lucky charm anklet her mother gave her followed by her Hannah wig. Now Lilly and Robby must convince her that her luck and talent didn’t come from the jewelry but from her belief in herself.
When Miley tells Lilly and Oliver she's secretly dating Jake again, they agree to help her keep the secret from her father. In order to sway Robbie to appreciate Jake, Miley devises a plan to date one of her band members - but the plan backfires!
Miley stretches herself too thin when she tries to work double duty by attending Hannah appearances and concerts and rushing home to Malibu as Miley in order to serve as Oliver's new co-host on a local radio show.
Jake returns and stuns Miley with the news that he is getting married to her socialite friend Tracy. After failing to talk some sense into Jake, Miley enlists Lilly's help in trying to stop the wedding.