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Andy's grandmother also happens to be Byron's girlfriend.
After seeing how much charity work Byron, Keith, and Wendy do, Andy and Jessica feel guilty, so they join a program to help prisoners channel their rage with a writing contest. But Andy's "charitible" work becomes more about himself when he discovers the prize is something he covets.
Wendy writes a medieval short story about her relationship with Keith, and Byron unintentionally becomes a pimp.
While working on a manual for a deep fryer, Byron proposes livening it up with a cartoon character. Andy tries to sarcastically shoot the idea down by suggesting a cartoon dog that tells people stupidly obvious facts, but when executives aren't thrilled with Andy's manual, Byron suggests the "Duh Dog," and the idea takes off. Meanwhile, Keith becomes addicted to fried food.
Andy is asked to baby-sit Jessica's nephew, and ends up being blackmailed in the process.
"A grumpy, constantly bickering and fighting elderly couple" clean apartments and seem to respond when verbally abused by "usually meek and gentle little Byron," to Jessica's initial horror. Meanwhile, Andy starts going out with his maid, then gets a lot more than he bargained for.
Freddy Pickering just inherited control of Pickering Industries, but Andy and the gang wonder if Freddy should be in control of anything. Freddy intentionally tries to cause dissension among the group. And he succeeds, to a degree, when he promotes Andy for standing up to him. To get back in his pals' good graces, Andy asks Freddy to include them on a trip, where they learn if Freddy is merely a rich eccentric, or a rich lunatic.
Andy finds out that the reason Wendy moved to Chicago was to pursue her dream of singing, but her career hasn't taken off. When Wendy decides to quit singing and pursue her other dream of marriage and a family, Keith, put on the spot about their relationship, conspires with Andy to help Wendy's singing career.
After Andy eavesdrops on Jessica's neighbor's therapy session, he wants to date her.
Andy and Byron take on the topic of religion and conclude, albeit temporarily, that "life is meaningless." It seems that Byron has become a follower of Zumanism, which worships a giant, stunningly beautiful sheep. In preparing for his sacred rite of passage, he studies with the minister's comely daughter. But sex is prohibited until after Byron's "Zuminion," leaving Byron in an aggrieved state--until Andy encourages him to violate the religion. But there are consequences. Meanwhile, to prove she's not shallow, Jessica tries to ignore the appearance of an otherwise great guy.
Andy and Byron find themselves in a battle to convince Jessica to pick them for a business trip to France, with each promising all manner of both work and non-work related favors.
Twin brothers are swapping Jessica, and when Andy finds out, he contemplates how to tell her. Meanwhile, Wendy helps Byron recover from an injury, and eventually has to play mother as much as nurse.
Andy and his co-workers compete for the finder's fee offered to the person who brings a new writer into the company, which is said to be looking for a "person of color." Although Andy wins the prize, he ultimately loses when he makes offensive comments about the new employee. Meanwhile, Wendy, whose candidate meets with tragedy, tries to make up for the money she lost out on by taking on a task that gives her a new distinguishing characteristic.
