Leo gets a job as a dispatch rider and more than meets his match in new prankster-loving boss Kat. Pam invites Peggy over for dinner now that they are 'virtually in-laws', with the catering to be provided by Tony's cafe. James, however, is distracted when Anji presents him with some life-changing news and Tony finds himself having to improvise a rather more modest repast. When Charlie gets thrown out of his lodgings, Pam plays trans-Samaritan and offers him Leo's room. Judy and Leo go on a double date with Jackie and Dean... and Charlie. If Dean had a ton of questions to ask about Judy, he has a whole lot more when he discovers that Charlie is trans too.