Dr. Katz gets the sudden urge to play the board game "Guess Who" with Ben. During the game, Katz sees the reflection of Ben's pieces in the TV screen and guesses correctly, annoying an oblivious Ben. Katz eventually comes clean about cheating, and offers to leave the apartment for a night as self-punishment. But in the process of saying where he'll probably be staying (the Hilton), Ben wants to come along.
Dr. Katz loses his day planner, and enlists Ben's help to find it while he's at work. Katz confides in Ben that the day planner contained chapters of a self help book he was writing. It turns out Ben wedged the day planner under their air conditioner to stop its shimmying.
Dr. Katz installs a new phone system in the office, but it has numerous bugs: When Ben tries to call the office from home, he is instead re-routed to Laura's home. Additionally, the phone calls often cut out without warning.
Ben wins $500 in a lottery scratch-off game and uses the money on an expensive dinner at a five star restaurant, with Dr. Katz and Laura as his guests. In the end, the restaurant bill ends up over his $500, forcing him to rely on Katz and Laura to pay the rest.
Ben wants to make author his full-time job, and for his first book, plans to write memoirs of his life so far. He dedicates the book to Dr. Katz, rationalizing that by the time he finishes the book, Katz will be dead. As with most all job ideas, though, Ben gives up by the end of the episode.
Dr. Katz gets a call from an old flame and patient Sharon Myers, whom he referred to another therapist because he felt unprofessional dating one of his patients. However, he does agree to a drink with Sharon to tell her that he can't start seeing her as a patient again.
Dr. Katz enlists Ben's help in reorganizing Katz's bedroom closet space. Ben schedules appointments for various closet companies. However, the company that Ben chose actually makes Katz's closet worse.
Ben gets the bug to be outdoors and asks Dr. Katz if they could do some camping and biking over the weekend. However, things don't pan out, and they end up staying home as usual, recording their "wild" weekend of pigging out on food and watching TV on Laura's camcorder.
Ben is runner-up in a contest to ride in a traffic helicopter. He hopes something will happen to the winner so he can take their place, and he even practices how he'll behave in the helicopter. But things go according to plan.
A story appears on the news about a balding man in his late forties breaking somebody's mailbox. Ben jumps to conclusions and thinks Dr. Katz performed the crime, and continues to think that, even after the real culprit was arrested.
Laura has been taking many afternoons off without saying where she's going. Dr. Katz and Ben are both naturally suspicious, and Ben sets out to be a detective to find out what she's been doing. He doesn't find anything in his "detective work", though; Laura admits she's been going to traffic school when confronted by Dr. Katz.