Miley's school has arranged a trip to Washington DC. But Lily cannot afford it, so Miley tries to give her the money but she won't accept it. So Miley tricks Lily into thinking a stranger has offered to pay her $500 for her baseball cap, but Lily soon finds out and is upset with Miley.
Hannah must learn to be the role model that everyone expects her to be after she causes a havoc by stating on TV that she doesn't like all vegetables. Meanwhile, Oliver and Jackson become models for a dating site, but it has a catch.
Hannah pretends to date a celebrity she can't stand to get in the news. Jackson thinks that he has to cheat on a test in school. Then, when his answers melted from his hand, all of those answers ended up in Jackson's head; he memorized all of the answers.
Miley gets a chance to rewrite her history with her brother after a knock to Jackson's noggin results in Amnesia. Jackson only pretended to have amnesia to impress Miley. Rico pays Lilly to pose as his sweetheart.
Miley returns from filming a movie and finds that Lilly and Oliver have started dating. There is something about Lilly that Oliver doesn't like and there's something about Oliver that Lilly doesn't like. Jackson gets an interview with a university and lies about himself to the representative in order to have a better chance of admission.
Miley tries to convince Lilly and Oliver that she likes being single, but they keep trying to set her up with dates. When she meets Traci's boyfriend "faux beau" Adam, she decides to use him to fool her friends into thinking she found someone that she likes. Adam cancels at the last moment but sends his uncouth friend Ralphie in his place.
Miley and Oliver become temporary deejays at a teen-oriented radio station after the regular host takes an unexpected leave. Meanwhile, Rico lets Jackson run the snack shack and he hopes that it will lose money and his dad won't be able to sell it.
Miley has restarted her relationship with Jake Ryan but has her doubts about telling her father straight away as she fears that everything she and Jake have been through in the past has caused her father to dislike Jake. However upon witnessing how much Robbie Ray dislikes bad-boy musician Jesse, Miley comes up with a plan to get Jake back in her fathers good books again.
Miley's plan to get Jake back in Robbie Rays good books again worked out much to Miley's pleasure, however little did Miley know that she would begin to develop feelings for Jesse in her attempt to make Jake look good. Miley is torn between who she should choose and who could ultimately be the one for her.
Hannah Montana is taking the teen cruise to Hawaii on the S.S Tipton to her concert. While on the ship she loses her lucky anklet that her mom gave her before her first concert. She thinks because she lost her anklet that's why she is having all this bad luck. The maid, Lydia, finds it in her cabin and as she is giving it to Mr. Moseby London snatches it away. When Hannah sees that London has her anklet she tries to get it back. When she tells London the diamonds are fake London drops the anklet into the ocean. As she is pouting about the anklet her wig is picked up ...
Miley is desperate to keep Lilly and Oliver together after she mistakenly concludes that Oliver is falling in love with her instead. But Oliver was only saying that he loves Miley to practice so that he can say I love you to Lilly.
Jackson agrees to forgive and forget after Miley humiliates him, but she doubts his sincerity once the media finds out something shameful about Hannah. City slicker Rico will have to do more than just tow the line if he wants to win the heart of a country hottie.
Mamaw Stewart comes visiting with her old car, and Miley, Jackson and Robby think it's time to buy her a new one. However, they don't realize how attached she is to the old one. Meanwhile, Oliver forgets his and Lilly's 100th dayaversary.
Oliver becomes an overnight sensation after performing on a TV talent show and the success quickly goes to his head. Miley and Lilly decide that the only way get their old pal back is if Hannah, who will be a judge for the show's finale, persuades the other judges to vote against Oliver.
An apologetic Miley plans to make up for the fiasco that Hannah caused at Lilly's last birthday with a special girl's night out. Unfortunately, she ends up stranded in the middle of nowhere on the big day, which leaves Jackson in charge of keeping an increasingly upset Lilly busy until Miley arrives.
Miley is trying to audition for the starring role of a cartoon duck. But she doesn't know how to make a good impression at the audition. Kyle, the professional voice actor helps her. Rico utilizes fancy restaurant gadgets for decorations. Robby Ray learns to text and bothers Jackson with it.
Lilly leans on Miley for support, when the obsession for perfection causes Lilly to lose her first job. Lilly stays at Miley's house because her mom is going to be disappointed with Lily if she finds out that Lilly got fired from her job.
Lilly's Mother gets a job in Atlanta, but Lilly doesn't want to go there. Miley decides that Lilly should move in with her, but being roommates quickly takes a toll on the girls friendship. Lilly decides to move in with her dad but later on, Miley talks to her and Lilly moves back in with her.
Miley starts to miss her old life in Tennessee. She dreams about blue jeans, her horse. Oliver gets an offer to go on a concert tour, but he won't be able to see Lilly for six months. Jackson thinks that it's time for him to move out of the house.
Jackson likes his new home in his new bachelor pad, but finds out that the place is a crumbling wreck. Miley is having second thoughts of going back to the simple life in Tennessee. Oliver is thinking of giving up the tour to be with Lilly, while Lilly tries to figure out what she will do without Oliver and Miley in her life. Jackson decides to move back in with his family.