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.