Jonathan is hired by a police officer to erase the hard drive of an S&M club computer to prevent potentially embarrassing information from coming out as the officer has received word that the club is about to be raided. Leah breaks it off with Ray. George is asked to cut back on expensive meals to prevent the Magazine from going under.

Jonathan is hired by Richard Antrem, George's nemesis and boxing foe, to investigate Richard's suspicions that his wife Priscilla, George's ex, is having an affair. Jonathan's insecurities resurface when Stella announces she's not over her first love. George has a new female urologist; Ray plots to win back Leah by penning a comic book.

George worries about remaining “intact” after getting some sobering news from his new urologist, Dr. Kenwood. A bad day for Jonathan gets worse when a pair of S&M henchmen kidnap him. They demand a ransom which calls “GI” George & Ray to action.

Jonathan attempts to repair the relationship between a poet/limousine driver and his wife. Ray has a meeting with Kevin Bacon.

Leah hires Jonathan to help find her new dog, “Little Ray.” Ray joins Jonathan in the search for the dog, getting some inside help. A reflective George heads to the hospital for surgery.

A dermatologist enlists Jonathan to deliver a letter to his intended at an Asian health spa. Jonathan takes Ray to the spa for his birthday, with George and his new chauffeur Vikram in tow.

A mad stalker imperils Ray on the eve of the Brooklyn Comic Con. With the help of Officer Drake, he and Jonathan piece together leads to track down the perp. George decides to make a stand at work. Jonathan has another battle with his nemesis, Louis Greene.