Oliver has a huge crush on Hannah Montana, but his feelings of love are not shared by Miley. No matter what she does, she can't seem to make Oliver realize that he & Hannah can never be - until Lilly comes up with a plan to burst Oliver's love bubble. Jackson's proud to be the owner of a "Brand New" used car that he bought with his own money, but the joy fades once he learns that this particular kind of car is only driven by girls.

Miley and her friends want to meet Ashton Kutcher at his movie premiere and Jackson and Cooper want to meet the beautiful girls who want to meet Ashton Kutcher. So both Miley & Jackson decide to disobey their father and sneak out. The super-sneaky siblings get a surprising eyeful when they spy their dad at the movie theater on a date. Miley becomes upset because he lied to them by saying he would be at a meeting and she thinks he's trying to replace their mother.

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.

It's Miley's birthday! Robbie is trying to find something special for his little girl. Miley tells Lilly to steer Robbie to the right clothes, but it still doesn't work. Now Miley has to wear a tacky sweater to her birthday party. Meanwhile, Jackson is trying really hard to give Miley a birthday cake and not mess things up (again).

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!

Sick of Amber and Ashley constantly winning the school's charity fundraiser, Miley, Lilly, and Oliver team up to raise more cash than the girls. Jackson needs Cooper's help if he wants to beat Robbie at ping pong.