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 go to Oliver's head, 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 see him giving her candy. When they learn that Oliver is secretly dealing with the news of being diabetic, they 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.

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 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 to 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.

Lilly and Oliver decide that they need to fix Miley up with a boyfriend so that she’s not the third wheel when they all go out. Miley instead takes matters into her own hands and “hires” a date to get Lilly and Oliver off her back.