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!

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.