Henry's girlfriend Heather breaks up with him almost immediately after they move to Chicago together, leaving Henry shell-shocked, broken-hearted, out of a job and out of an apartment - all on the same day. He learns the only apartment opening in their building is with Larry, a vain, flashy, yet loveable rogue who agrees to take Henry on as a roommate now that his previous roommate, Brad, has moved in with his controlling fiance, Tina. Larry relishes the opportunity to "build a better Brad" and mold Henry into an image of himself, but Larry quickly learns there are lessons he can glean from Henry as well. In an attempt to get Henry back on his feet, Larry sets him up with a job interview with his best friend, Amanda, who works at a local bank. After a very shaky interview, Amanda agrees to give Henry a job, providing him with another building block to put his life back together. One constant at Larry's apartment is four o'clock martini time, and it's not long before country boy Henry is ordering another round.