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Fanciful series about an aspiring writer who imagines alternative life scenarios while working for a big company.
Andy and his co-workers compete for the finders fee offered to the person who brings a new writer into the company, which is said to be looking for a "person of color".
Andy suspects Jessica is being shared by twin brothers. Wendy volunteers to nurse Byron back from an injury.
A business trip to France is at stake as Andy and Byron jockey for Jessica's favor, with Andy promising to care for her cat, which he loses.
Byron has become a follower of Zumanism, which worships a giant, stunningly beautiful sheep. Meanwhile, to prove she's not shallow, Jessica tries to ignore the appearance of an otherwise great guy.
After Andy eavesdrops on Jessica's neighbor's therapy session, he wants to date her.
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.
Freddy Pickering inherits control of Pickering Industries. But Andy and the gang wonder if Freddy should be in control of anything.
Andy sleeps with Jessica's cleaner causing Jessica to replace her with an old married couple recommended by Byron.
Andy is asked to baby-sit Jessica's nephew, and ends up being blackmailed in the process.
While working on a manual for a deep frier, 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.
Wendy writes a medieval short story about her relationship with Keith, and Byron unintentionally becomes a pimp.
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 into writing.
Andy's grandmother also happens to be Byron's girlfriend.
