Miley's at the dentist, without her dad and it doesn't end well. When Miley insists on going to the dentist without her fathers hand to hold, she ultimately can't go through with the treatment, but doesn't admit it to Robby. Her appearance as Hannah on a popular food show goes completely awry as a result of her swollen tooth.

Miley agrees to go out with a charming boy named Connor for the holidays. Connor's elfin stature and his job helping Santa at the mall, however, clashes with her idea of the perfect guy. The neighborhood Scrooge Mr. Dontzig offers to get Jackson into the college of his dreams, but only if Jackson and Robbie do everything that he asks of them.