Oliver comes to visit Lilly and shows her a picture of Jake cheating on Miley. They try to keep this news from Miley, but when Miley says she wants Jake to come to visit, they decide to tell Miley the truth.

Robbie's feelings are hurt when Miley starts spending less time with him.

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.

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.

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.

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.

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 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.)

Amber and Ashley are up to their old tricks again, only this time Miley and Lilly devise a plan to give one of the girls a taste of her own medicine. A persnickety pooch named Oscar drives Robby and Jackson batty with its constant barking.

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.

After Lilly embarrasses her at a Hannah Montana concert along with added pressure from her "Hannah Friends", Miley decides to lie to Lilly and tell her that the birthday party for Kelly Clarkson that they were going to was called off. Miley attends the party as Hannah but must cover up her lie when she lands on the front page of the news. Jackson meets a beautician named Nina at work who asks if she could use him to practice on. He's more than happy to oblige the pretty lady, not knowing that it's one of Rico's pranks.

Lilly's pride takes a hit when she's forced to wear her awful-looking glasses right before a skateboarding contest. Hoping to help, Miley convinces her friend not to worry about her appearance and to go ahead with the competition. Miley refuses to take her own advice, however, when it's her vanity that's damaged. Jackson wishes Rico would disappear when he realizes that his new raise depends on Rico's opinion of him.

Hannah meets her idol, Isis, who inspires her to change her image to keep fresh. Hannah does this to impress the Sunshine Girls after being named Role Model of the Year. Meanwhile, Jackson befriends Rico.

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.

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.

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?

Uncle Earl comes to visit and expects Miley to help him become a rock star.

In an auction hosted by Donny Osmond, Hannah is up for bid in a special "Date with Hannah Montana" prize. Ray Romano makes an appearance at the auction, although Hannah doesn't know who he is. After a bidding war between Hannah's crush Johnny Collins and Rico, she has to take both on the date together.

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 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 adores her new beau, Josh, but is unsettled to learn that he despises Hannah Montana. After spending their whole date trying to get Josh to change his mind about Hannah, he decides to attend a Hannah Montana concert, but only if Miley will go with him. Sparks fly when Jackson meets a new girl who actually likes him for himself. Unfortunately, there are even bigger sparks between Jackson and Cooper, once Cooper realizes that Jackson's dream girl is his little sister, Olivia.

The Stewarts are having a busy week. Hannah Montana is about to perform for the Queen of England and the Queen's granddaughter; Jackson is in his school's volleyball championship; and Mamaw Ruthie is in town on a surprise visit. But when Mamaw only spends time with Jackson, Miley believes that Jackson is Mamaw's favorite.

Miley & Lilly play matchmakers for a Hannah Montana fan named Becca. The object of Becca's affection is Oliver & the girls manage to get them together. Oliver wishes that they would have stayed out of his love life when Lilly and Miley find out something upsetting about his new squeeze. Jackson learns why the chicken crossed the road... to get away from spoiled Rico and his demands!

A sneaky photographer takes a picture of Hannah and Jackson, causing everyone to think that Jackson and Hannah are a couple. Meanwhile, Oliver has a school assignment with Sarah and he finds himself liking her.

The Stewarts' nasty neighbor gets Miley and Jackson to look after his equally nasty niece. Robby gets the flu and Roxy has to look after him.