Rapunzel notices that Old Lady Crowley never smiles, and decides to brighten her day. She first tries presenting Crowley with some delicious treats, only for them to be rejected. She takes her to get a new hairstyle, but her frown remains the same. She tries to get her to laugh by having Pascal slipping on a banana peel, but she still does not smile.
Rapunzel tries everything from ventriloquism, music, juggling, to "ugly face" impressions, but still Crowley does not smile. Eventually, Rapunzel gives up. For eighteen years alone in the tower, Rapunzel and Pascal had always, up until now, found a way to a smile on each others faces. Hearing the fact that Rapunzel spent eighteen years alone in a tower with complete silence and no one to talk to, Crowley listens and asks her about it. At last Rapunzel sees a way to make her smile. The next day, Crowley finds in her room a pair of earmuffs and a blind with a painting of a beautiful landscape all made by Rapunzel. She shuts the blind and puts on the earmuffs. The sound of silence finally puts a smile on Crowley's face.
- Three of the scenes where Rapunzel tries to make Crowley smile are references to scenes seen during the song When Will My Life Begin.
- Rapunzel and Pascal doing ventriloquism.
- Rapunzel playing the guitar.
- The papier-mâché head.
- The Wilhelm scream is heard when a guard trips on the banana peel.