Caroline in the City (1995)

Episode Overview

Del has enlisted Caroline and Annie to voice his latest promotional video. However, when he arrives to pick them up, they must first present a puppet show about menstruation to the boss. While Annie is in her office, Caroline rummages through Richard's desk for a highlighter and stumbles upon his divorce papers, which leads to an angry confrontation over her breach of privacy. Annie quickly grabs the papers, but when they inadvertently get sent down the mail chute, she and Caroline must navigate the unfriendly mail room staff to retrieve them. Meanwhile, Richard and a surprisingly enthusiastic Charlie perform the puppet show for Mr. MacDermott, who reveals he’s only doing the animation as part of his community service. Caroline later finds out that Richard's divorce papers are two months old and he hasn’t signed them, meaning he’s still technically married, prompting her to confront him.