Charles's girlfriend gets him a job at the local paper filling in for the vacationing advice columnist. One of the first letter writers he has to give advice to appears to be Sarah, and the problem she wants advice for sounds quite racy.

When Charles is unsure about what to major in, he gets a visit from his uncle from Brooklyn who tries to get him to quit school, leave the Powells and join the pickle business.

When Buddy is not himself after being dumped by his girlfriend, Charles and Mr. Powell decide to build his confidence back up by sending him to a self-improvement program. However, it gives him too much confidence and he becomes very rude to everyone.