Talking Teddy / Principal Interest.Talking Teddy: When Theodore gets to pick the TV show, his bear recommends Talking Teddy TV Fun Time. Unable to stand any more of the bear, Alvin convinces Simon to do something about it, so Simon comes up with the idea to program it to obey Alvin with the help of a keyboard that he created. The next night, Theodore seems a little upset by the change in his Teddy. While Alvin abuses his control of the bear, Simon tries to dampen Alvin's actions. After Simon wants to end the charade, Alvin steals the keyboard, hides it, and continues to take advantage of Theodore, much to Simon's displeasure. Finally Simon, unable to stand it any more, rewires the bear once more in order to teach Alvin a lesson. Once he succeeds in freaking out Alvin, Simon convinces Theodore to donate Teddy to a daycare program. In the end, Theodore returns with a new and improved Talking Teddy.
Principal Interest: The Chipmunks' new year at school starts, and Alvin immediately develops a crush on the new principal. However, to get past the principal's assistant, who is none other than Brittany, Alvin misbehaves on purpose and throws his classes into chaos in order to get summoned to her office. Tired of his attentions, the principal suspends him, but once home Alvin drives David crazy, who then meets with the principal to beg her to take Alvin back. Alvin sneaks in, believing that they are going on a date, only to discover that the principal is already married to another man.