The arrival of Maya's old college roommate Erin leads to an incredibly crazy situation. Maya tries to compete with her friend's globe trotting journalistic ventures by spending a night in a sewer in hope of getting her first hard-hitting news story in a year. In the meantime, Erin takes a break from her hectic schedule and has an affair with Elliott. Adding to the craziness is Jack's surprise birthday party, with Nina and Finch supplying his boyhood idols, crazy old Cowboy Pete and his orangutan sidekick. In the end, though, it's Maya who provides the biggest surprise of all.

What starts out as a normal, everyday office meeting turns into a huge enigma when the easygoing Jack suddenly loses his temper for no apparent reason and refuses to talk about it. The gang takes it upon themselves to discover the reason for his outburst, but with every lead they follow, the mystery just gets deeper and deeper. While this is going on, Finch tries to attract a pretty coworker by following Elliott's advice and playing hard to get.

Finch's complaints about doing petty errands bring an unexpected response from Jack- he hires a personal assistant, Kenny. Having his territory infringed on soon becomes the least of Finch's worries, as Kenny threatens Finch violently when Finch speaks up. To make matters worse, no one believes Finch because Kenny is all brightness and sunshine to everyone else. Meanwhile, Nina's attempts to quit smoking backfire in two ways: Nina becomes even more amorous than usual toward everyone, while Maya, mistaking Nina's nicotine patch for a Band-Aid, gets unwittingly hopped up on nicotine and becomes relentlessly hyper.

When Maya's first love John Kenny pops back into town, she becomes as happy as she's ever been, as the two find their old spark back in full force. However, Jack is angry about the whole thing, as he still has not forgotten when he walked in on the two of them fooling around one time. Maya then learns the true horror of the situation- the only reason they were separated in the first place was because Jack had pulled strings to get him into the Royal Shakespeare Company, and she becomes instantly fearful that he will once again begin to interfere with their relationship. Meanwhile, Finch uses a ""tough love"" method to train a new intern while Nina's television appearance is ruined when an old allergy acts up.