Miley tries to keep a relationship from forming after learning that Lilly secretly has a crush on Jackson and that Jackson secretly has a crush on Lilly.

Miley gets herself into a pickle with the law when she comes up with a scheme to use Hannah Montana’s celebrity status to get her driver’s license after failing her initial test. Meanwhile, Rico stays at the Stewart house.

Miley goes to the dentist by herself to prove to Robbie that she is brave enough to do it. But when she ultimately chickens out at the dentist’s office and doesn’t tell Robbie, her swollen tooth ends up causing trouble when Hannah makes a guest appearance on a popular cooking show.

Miley asks her dad for more money, and gets it. But now, she has to keep herself from spending it on stupid things.

Miley accepts a date with a cute guy who is considerably shorter than she is, but she ruins their evening by inadvertently referring to the difference in their height. At home, Jackson and Robby try to impress their neighbor so he will write a letter of recommendation to help get Jackson accepted to Robby's alma mater.

Miley lies to help Lilly raise money so that she can go on the class trip to Washington. Meanwhile, Rico hires Sarah in order to bug Jackson.

Miley decides to intentionally blow an audition Hannah Montana has for a movie with director Rob Reiner on purpose to make Oliver feel better about not getting to perform at the school dance. Meanwhile, Jackson uses Rico as a ventriloquist dummy after Rico destroys Jackson’s original puppet. (Special Guest Star Rob Reiner)

Miley gets herself into another fix when Hannah makes a bad comment about carrots while being interviewed on a TV show and her fans stop eating them. Now she has to find some way to fix things up before the situation gets worse. Meanwhile, Jackson and Oliver are disappointed when they find out that they were chosen to model for different reasons than they originally thought.

Miley’s decision about whether or not to fire Hannah’s new choreographer is complicated when she discovers that he and Robbie have become friends.

Miley has to face up to a lie that she told in order to show Jackson that what he plans to do is wrong when she learns that he plans to cheat on a test.

Jackson’s memory loss seems to be the perfect opportunity for Miley to change their relationship for her benefit. Meanwhile, Rico forces Lilly to pretend to be his girlfriend while his cousin Angus is in town in exchange for his help with her math.

Miley and Jackson have to figure out a way to get things back to normal in their school after Mamaw takes over as the cafeteria lady.

After returning home from shooting a movie for a month, Miley secretly discovers that Lilly and Oliver are dating. But when she asks questions to try to get them to tell her to her face that they are dating, she ends up accidentally causing them to breakup. Now she has to try to convince them to get back together. Meanwhile, Jackson lies at a college interview to try to make a better impression.

Miley has to choose between keeping a promise she made to go to prom with the school nerd or recording a duet with David Archuleta. Meanwhile, Robby tries to get Jackson to enroll for college. (Special Guest Star David Archuleta)

Lilly and Oliver won’t stop giving Miley a hard time over the fact that she doesn’t have a boyfriend, so she decides to pay an actor to pretend to be her boyfriend so they will leave her alone. But when the actor she paid backs out and sends his not so attractive roommate to fill in, Miley finds herself in a bigger mess than the one she started out in. Meanwhile, Jackson has a hard time believing that Rico’s act of kindness is genuine.

When Hannah goes to Las Vegas she discovers that Tracy is getting married to Jake Ryan. The question is can she stop the wedding?

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 in 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.

While on the deck of the S.S. Tipton, Miley loses the charm ankle bracelet that her mother gave her and when things start to go wrong, she is sure its because she lost her lucky charm. Meanwhile, Jackson opens a large package after Robbie forbids him to do so, and he suffers the consequences.

After landing in the hospital because of a skiing accident, Miley hears Oliver say I Love You. Assuming he was saying it to her, Miley tells Lilly and they concoct a plan to remind him of his feelings for Lilly.

Miley has an interview as Hannah and says something about Jackson and in order to get Jackson to forgive her she has to take her to Tracy's party, but at the party things get a litte crazy.

Robbie and the kids trade in Mamaw's old rust bucket for a regal new convertible. They are unaware, however, that Mamaw is extremely attached the decrepit car she calls Loretta. Rico is forced to play peacemaker, when Lilly and Oliver's constant quarreling drives his customers away.

Miley and Lilly find out that Oliver has diabetes, and they try to play food police at Traci's birthday party....

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. Robbie and Jackson must fight the law, when Jackson keeps receiving tickets for traffic violations that he didn't commit....

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 auditions to be the voice for a cartoon duck, but it doesn't go well. Jackson is tired of Robbie treating him like a child. Rico outfits the Surf Shack with high tech equipment.

Lilly leans on Miley for support, when the obsession for perfection causes Lilly to lose her first job.

Miley offers to share her own room with Lilly after Lilly's Mother gets a job in another state, but being roommates quickly takes a toll on the girls friendship.

Miley starts to miss her old life in Tennessee. Oliver gets an offer to go on a concert tour, but his joy is dampened when realizes that he won't be able to see Lilly for six months. Jackson decides that it is time for him to leave home.

Jackson makes himself at home in his new bachelor pad, but quickly find out that the place is a crumbling wreck. Miley mulls over the idea of going back to the simple life in Tennessee. Oliver contemplates 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.