Julie sets Dr. Katz up on a blind date with Beth, a woman from the Midwest. Eventually, Beth cancels through Julie. Meanwhile, Ben wants to have a tenth anniversary dinner with Dr. Katz, with the anniversary being ten years since Katz and his wife split up.
Dr. Katz brings a bowl of fruit to the office and sets it on Laura's desk. They eventually get rid of it, because it's going rotten and attracting flies. Meanwhile, Ben gets ideas for new careers and hobbies, such as cake decorating, roller skating, and truck driving. He doesn't follow through on any of them.
Ben wants to change his image. He ultimately decides on an earring, though he starts with a tacky-looking "tape-on" earring before going for the real thing. Dr. Katz doesn't approve. However, Ben gets cold feet at the mall and ultimately doesn't go through with it.
While looking for his birth certificate, Ben discovers that Dr. Katz was a hippie back in the '60s, and had an old flame named Sharon Koppleman. This makes Katz nostalgic, and takes his guitar to the office, wanting Laura to humor him by pretending to be Sharon from his old folk music duo.
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.