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Henry Beckman has a girlfriend who convinces him to move to Chicago to work for her uncle. But his life is sent into a loop when she dumps him, which causes him to lose his job and to be thrown into an apartment with Larry, a man who has his own surreal opinions on life and women. Larry sets up Henry with a new job and life begins anew. Of course, one of the house rules is that every day at four is Happy Hour.
Henry finds a mix CD of love songs and gets details about Larry's one true love, Molly. Amanda is concerned when a doctor in her gynecologist's office cancels a date with her.
It's Larry's birthday and his friends all forgot about it.. all except Henry who got him a lame camping trip as a present.
When Larry discovers that Henry is hanging onto an engagement ring that he had planned to give Heather, he tries to get Henry to sell the ring and buy a wine refrigerator.
When Henry dates a girl named Shauna, Larry warns him to stay away from her. After Henry ignores the warnings he returns to Larry to help him get out of the relationship.
Tina is planning a Thansgiving dinner, and her mother and sister are is planning to visit. Unfortunately Brad makes too good of an impression on his mother-in-law as she puts the moves on him.
Larry and Tina host separate Halloween parties and Brad begs everyone to attend Tina’s dreary party. Amanda and Heather wear identical sexy costumes to Larry’s party.
With Tina and Brad’s rule on the tenants’ association coming to an end, Larry and Henry decide to run against them. Amanda gets bored with her doting husband.
Henry's parents are coming for a visit and he fears they'll be disappointed in him. Larry and Amanda have prejudices against them. Tina gets a job but she doesn't like Brad's excitement over it. Everyone may have to rethink their opinions.
Larry and Brad almost get into a fight in a bar, and Henry calls the police to save them, forgetting that all three are impersonating police officers to impress women.
Everyone likes Amanda’s current boyfriend except for Larry, who gets a ‘bad vibe’ from him. Although Larry always protects Amanda, he goes too far this time and hurts her feelings.
It’s Christmas and Larry’s friends leave to be with their families, however they then decide to stay with him because all flights out of Chicago have been cancelled. However, at the apartment, the only food available is a mail-order ham that arrived for a neighbour who has died
Larry’s T-Shirt business soars in popularity after George Clooney is seen wearing one of his shirts, however the reverse happens with Kevin Federline. Heather then saves the business by changing the company slogan.
