With the green light for his new reality show in jeopardy, George caves in to network demands and asks Claire to move in - with some strict conditions.
George has a major crisis of faith when Claire announces plans to convert to Judaism.
As George juggles calls from Doug and Claire, he gets pulled over by a bike cop for a series of infractions. His plates are expired, his license is expired and he's clearly a distracted driver. But it's the digs about his nonchalant driving that really stick in his craw as he heads out for dinner with Claire. Bragging about his skills, he nearly wipes out a pedestrian. The incident leads to a shouting match with the man, Gerry, a producer who brags that he's landed Jack Nicholson for a role in his new movie. Irked about Gerry's success and having to wait for a table at a chi-chi new restaurant, George lies to the hostess to grab an empty table for four. They are seated immediately after he claims Jack Nicholson is meeting them for dinner.
George regrets his decision to hear a pitch from Claire's coveted hair stylist.
When George is asked to appear on a This is Your Life-type show, he is burdened by the discovery that his formerly estranged childhood friend is now a professional killer.
George boasts to Doug and Alan about turning down a two hundred thousand dollar commercial deal for a product he's averse to promoting. But while the notion of shilling an extremely personal body product seems unsavoury, he's happy to demand a fee for an appearance on "Between Friends," a This is your Life-style program that reintroduces people from your past. When George picks up his estranged childhood friend Dave at the airport, his worst fear is that they'll still have nothing in common, which could mean making some bad TV. But things escalate to terrifying levels when, after a scary, turbulent flight, Dave begins to reassess his life and confesses that he's a professional hitman with dozens of kills to his credit.
As George becomes more aware of how different his tastes, references and sensibilities are from Claire's he begins to fret about their relationship. When he solicits Doug's advice, the two men agree that their relationship acumen and insights far surpass women's intuition. Still, it's clear these paranoid feelings have George unhinged. Doug's solution is a cohabitation agreement, a sort of pre-nuptial document for the unmarried, to make sure Claire doesn't clean out his considerable assets if things go awry. Unfortunately, as George indelicately broaches the subject with Claire, she's irate. Well aware of their age and taste differences, she accepts them. Furthermore, if George is so adamant about this foolish contract, she's moving out. His hand forced, George needs to rethink his position fast, before she walks out the door.
Unsettled and miffed about his new domestic situation, George is in the doghouse after he insults Erica the nanny's work ethic, then Claire's intelligence. Doug advises him to buy Claire a gift to apologize. So George pops into the hardware store to grab something. The hardware guy recommends flowers. They're a hit, but he misses the mark again when he suggests caging Bruno the Rottweiler. So off he heads for a better make-up gift before meeting with his broker. But before he can get down to business, Doug drags him to The Communal Mule coffee shop to admire the most beautiful woman in the world. George is overwhelmed. He hits on her pretending he's doing a show about how unhappy beautiful women are only to discover her life is amazing.
After George picks up Claire from an extravagant shopping adventure, his cell phone rings. To his shock, it's the most beautiful girl in the world who he met at a coffee shop and offered a show. He hangs up immediately, claiming it's a telemarketer. Claire is suspicious. George vents to Doug about the call. The previously happy beautiful woman has broken up with her boyfriend and is now despondent and desperate to appear on The Ugly Side of Beauty, the non-existent show he claimed he was producing. To get her to stop stalking him, George begs Doug to date her and leaves for a meeting. George meets with Weldon, a journalist with a pitch about his life as a beat reporter. As George gushes over the idea of corrupt city politics, the beautiful girl interrupts - berating him for dumping Doug on her and lying about the show.
When George and Claire attend the screening of a pretentious art film, it's all George can do not to scream in agony. And when the director approaches them in the lobby afterwards, George can only offer comments on the man's suit. Embarrassed, Claire is effusive and grabs the attention of the director who decides to cast her in his new film, a vérité love story starring him. After hearing the story of the encounter, Doug suggests that in the future, George enlist the universal "f'ed up" in response to people seeking feedback. In most circumstances, they will take it as a compliment. The theory proves true when George meets with Scott and Matt, a pair of extremely stoned up-and-coming writers. Despite their questionable talents, George's words prove encouraging. Now being sued by the most beautiful woman in the world.
Hung-over and plied with Tylenol by his assistant Alan, George is clearly suffering when Doug stops by his office to chat. George regales him with an astonishing story involving Claire's friend Anita,a Swedish supermodel, and Gunnar, her hockey player husband. Apparently despite Gunnar's athletic prowess, he's unable to impregnate his wife and they'd like to enlist George for the assist. Flashing between George's dramatic embellishment of the scenario with Doug and the actual meeting, negotiations and sealing of the deal, George is obviously incredibly pleased with the strange sexual transaction. Suddenly, George is bringing home a murderer for a few days plus has planned a dinner party with their mutual friend Allen, a successful orthodontist.
George takes his kids, Sidney and Abe for a fancy meal where they suggest he trade-in his BMW for a Prius, especially given he is trying to produce a project with an environmentally sensitive film company. Later on in the day, during a shopping excursion with Claire, she asks him to buy a car. Considering a big-ticket purchase like that akin to a serious commitment, George recoils. Doug suggests George draw up a 'pre-purch' agreement, a sort of pre-nuptial that will make the car defer to him if their relationship ends. When Claire hears of the idea she's insulted. To make amends and prove his commitment to her, he offers to drive her kids and their nanny to a birthday party hosted by a film financier. At the party, George wreaks havoc even getting into a shoving match with the clown.
George complains to his agent about his struggles to get a new project off the ground. The agent tells George his ideas are stale and he needs an online, multi-platform approach to be relevant to a younger demographic. George is miffed with his bluntness and the apparent inanity of his suggestions. When George meets with the network executives, they team him with Lewis Weinstein, a kid who is a viral sensation with HeyBully, a virtual way to vent aggravation. George leaves the meeting clueless about the concept and feeling even more irrelevant. Doug's solution is retirement. After all, unemployment has served him well. But Claire quickly puts the kibosh on that, saying he'd drive her crazy and she'd leave him.
