Jackson and Lilly toy with the idea of going out together, while Miley thinks of ways to nip their romance in the bud.

Miley is riding high when she begins Drivers' Ed, but she comes crashing down to earth after she learns that the class is not the easy ride she thought it was.

When Miley insists on going to the dentist without her father's hand to hold, she ultimately can’t go through with the treatment but doesn’t admit it to Robby. Her appearance as Hannah on a popular food show goes completely awry as a result of her swollen tooth.

When Miley asks for a raise on her allowance, Robby decides to teach her about fiscal responsibility.

Miley agrees to go out with a charming boy named Connor for the holidays. Connor's elfin stature and his job helping Santa at the mall, however, clashes with her idea of the perfect guy. The neighborhood Scrooge, Mr. Dontzig, offers to get Jackson into the college of his dreams, but only if Jackson and Robby do everything that he asks of them.

Lilly holds a yard sale to raise money for a class trip to Washington, D.C., and Miley gets a man to buy Lilly's hat for a thousand dollars. Miley helped her even though she didn't want her help. Miley and Lilly reconcile when they stumble into a White House press conference with Miley mentioning that Lilly is more of a sister than her best friend. Meanwhile, Rico hires Sarah to work at Rico's because he knows it will annoy Jackson, but then realizes that he isn't happy with Sarah.

Miley, dressed as Hannah, blows a movie audition with director Rob Reiner on purpose to make Oliver feel better about not getting into a band. Meanwhile, Rico destroys Jackson's ventriloquist dummy, and therefore Rico is forced to act as the dummy for a birthday party.

Hannah is on a talk show and says she doesn't like carrots and books and her fans have no choice but to do likewise.

Robby becomes close friends with Hannah's new choreographer, making it hard for Miley to get rid of him. Oliver doesn't like his new bossy girlfriend and gets Jackson's help to rid himself of her.

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. Robby clashes with Rico.

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 at school after Mamaw takes over as the lunch lady.

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 get out of going to prom with the school nerd and when the chance comes for her to record a duet with David Archuleta, she uses it as the perfect excuse.

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, middle-aged 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.

Miley runs into Jake Ryan in Las Vegas. She's shocked to learn that he plans to marry Traci, so she plots to stop the wedding. Meanwhile, Rico tries to disrupt Jackson's date.

Miley and Oliver become temporary DJs 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 agrees to go steady with Jake again, but she worries that all of the times she complained about Jake might have turned Robby against the young man. When she learns that Robby dislikes Jesse, a troublemaking teen guitarist in Hannah's band, Miley hatches a plan to make Jake look great.

Miley's scheme to get Jake back into Robby's good graces works out beautifully and she believes that they are headed for a happy ending. Things change, however, when Miley realizes that Robby misjudged Jesse's true nature and she now finds herself drawn to the handsome musician.

Miley is desperate to keep Lilly and Oliver together after she mistakenly concludes that Oliver is falling in love with her instead.

Hannah reveals something embarrassing about Jackson in an interview and while she tries to make it up to Jackson he appears to do the same thing to her, or did he?

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 to 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. (Due to negative feedback, the episode was re-edited from the original titled "No Sugar, Sugar" that aired in some countries.)

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 to 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. Robby 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.

Hannah assumes that she will take to voiceover work like a duck to water. Jackson is tired of Robby treating him like a child. Rico outfits the Surf Shack with high-tech equipment.

When Miley accidentally gets Lilly fired, Lilly becomes the Stewarts' housekeeper.

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 finds 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.