Hannah Montana (2006)

S3E15 Once, Twice, Three Times Afraidy

Miley is constantly teased by Lilly and Oliver for being single, prompting her to hire an actor to pose as her boyfriend to silence them. However, when the actor bails and sends his less-than-charming, middle-aged roommate in his place, Miley's plan backfires spectacularly. Meanwhile, Jackson struggles to accept that Rico’s seemingly nice gesture might actually be sincere.