Miley, Lilly, and Oliver compete against Amber and Ashley to raise money.

When Paulie The Papparrazzo gets a shot of Hannah and Jackson together, the world thinks Jackson is "Hannah's" new boyfriend.

There is a show called Singing With the Stars, and whoever wins, will sing with Hannah Montana. At school, Amber says that she could win. She then goes into the bathroom and Miley says that she would make sure that Amber didn't win. But then she hears a terrible voice coming from the bathroom and Miley said she WOULD make sure she got in because she wanted Amber to be humiliated on t.v. At lunch, Miley then calls Amber and says that she would be in Singing With the Stars and singing with Hannah Montana. Then Amber says it aloud that she is going to be singing with Hannah Montana on Singing with the Stars and asks everybody if they want to hear her song. Then Ashley starts to sing and she sings horrible. But Amber tells her to stop and she begins to sing. Everybody sees that she has a great voice and then Lilly and Miley come up with a plan to make Amber be humiliated on t.v. At the show, around 2 minutes before starting, Amber confesses to Hannah that when she was little, people made fun of her, and she was feeling really scared/nervous that that would happen again. Hannah decides to go through where Amber is supposed to go through, and she gets humiliated because it makes everything poof up, etc. That was the entrance that Amber was supposed to go through. And that's pretty much it.

After Lilly fails to receive or catch Miley's passes for flag football in gym, Miley and Lilly fight. In order for them to reconcile again, Oliver handcuffs Lilly and Miley together, wrist to wrist, and accidentally loses the key.

Miley gives Lilly a makeover for a school dance which Matt Marshal is taking her to. After Matt stands her up, Lilly takes him to Teen Court.

When Lilly records a song for her mom and sounds horrible, Miley and Robbie Ray doctor the recording. Thinking she is a great singer, Lilly challenges Amber to a sing off.

When Robby and Lilly's mom Heather make plans to go out on a date, Miley and Lilly get so excited, the're sure they'll hit it off and the two of them will become sisters, but all doesn't go as planned when Robby and Heather have a disagreement and the girls argue over whose parent is to blame.

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.

The Stewarts move onto their new ranch home, but Miley and Lilly are aghast that Robby Ray has moved Miley's old bedroom furniture, complete with white bunk beds, pink walls, pink bedding, dolls, a stuffed unicorn and Rainbow Piggy, into their new home, so they set out to make some changes. Meanwhile, Jackson must befriend an obnoxious new kid, T.J., in order to get close to T.J.'s beautiful cousin Siena, who lives next door.

Robby misses the deadline to register Miley for school, but when Principal Luger makes an exception for Hannah Montana, the problem is solved. However, Miley finds that attending school as Hannah attracts much more attention than she'd like. Meanwhile, Jackson is paranoid when Siena asks him out on a date.

Miley convinces Lilly that she should try to ride her horse, Blue Jeans. Unfortunately during her first ride, a snake bites the horse leading to injuries for both, including what could be a fatality for Miley's beloved pet.