In the premier episode, Larry jokingly refers to his wife Cheryl as "Hitler", offending his manager Jeff's conservative Jewish parents. Since Jeff cant go to the movies with Larry, Cheryl sets Larry up with a friend of hers. But a bunch-up in Larry's trousers results in many misunderstandings.
Larry and Cheryl enjoy their bowling double-date with Ted Danson and Mary Steenburgen, but it ends badly when Larry accuses the bowling alley of misplacing his sneakers. Later, Ted gets the wrong idea about Larry when he goes shopping with Mary at a downtown department store.
A bizarre chain of events finds Larry having dinner with a porno star (Bob Odenkirk). The party turns out to be one disaster after another when Larry breaks a lamp, is forced to take off his shoes, loses his watch, gets lost along the way, and has to do the dreaded "double goodbye". Meanwhile, Jeff undergoes emergency surgery and asks Larry to go to his house and retrieve his porno collection so Suzie doesn't see it.
Larry gets in a tense, heated fight with Cheryl, So to make up for it, Larry's secretary suggests that he buy Cheryl a present to make up for it. After having lunch with Richard Lewis and helping out a blind man, Larry spots the perfect present for Cheryl - a bracelet. Unfortunately, Richard Lewis is also coveting said bracelet.
Larry holds an elevator, and is denied his doctor's appointment. Of course, this causes him to miss an appointment with Diane Keaton. Cheryl hires an interior decorator who also happens to be Diane Keaton's, but the decorator wont give Larry Keaton's phone number.
Cheryl gives Larry an ultimatum - bury the wire in the backyard - or else! But the permit the city gives Larry requires six signatures from his neighbors, and that means having to be nice to them at all costs - or else.
Jeff buys a '57 Chevy and insists that Larry take it for a drive. At a stop sign, Larry mistakes the honking horn from an AAMCO commercial for the car behind him and yells at the other driver, who then hits the Chevy and speeds away. Luckily, Larry meets an antique auto mechanic at a dinner party who says he can fix Jeff's Chevy.
Thanks to Larry's manager, Jeff, Cheryl is up for a part in "The Vagina Monologues." Meanwhile, Larry runs into an ex, who asks him to attend a survivors-of-incest support group with her to lend moral support while she deals with her past.