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.

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.

Andy suspects Jessica is being shared by twin brothers. Wendy volunteers to nurse Byron back from an injury.

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.

The gang goes out-of-town to a co-worker's wedding and are all put in compromising positions. Jessica and an obnoxious mailroom worker get together, and Andy mysteriously ends up in bed with Byron.

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.

Andy finds his once private office is now to be shared the new Technical Illustrator to Andy's writings, a very timid and somewhat peculiar Byron.

Andy and his friends tangle with a cost-cutting executive named Praeger.

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.

Andy's grandmother also happens to be Byron's girlfriend.

Andy finds yet another officemate named Andy, and meets neighbors who idolize him from his frat days.

After Andy eavesdrops on Jessica's neighbor's therapy session, he wants to date her.

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's gorgeous new girlfriend makes a bigoted remark, and late-night partying becomes Jessica's MO for business success after a good meeting on no sleep.

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.

Everyone arrives at work Monday morning to an awful odor.

Freddy Pickering inherits control of Pickering Industries. But Andy and the gang wonder if Freddy should be in control of anything.

Wendy writes a medieval short story about her relationship with Keith, and Byron unintentionally becomes a pimp.