Miley repeatedly tries but fails to gently tell Robby that she's dating Jake Ryan again. Soon her dad winds up believing she's trying to hide something from him.  Now, to make Robby thankful for Jake, Miley pretends to date her bad boy band mate, Jesse, but gets in over her head, so it's up to Robby, with help from Miley's late mother, to help her navigate the predicament.

Miley is desperate to keep Lilly and Oliver together after she mistakenly concludes that Oliver is falling in love with her instead.