Four months after the first season finale, Ryan is in a mental institution, and has been for the past four months. He hasn't seen Jenna or Wilfred in that time, but, after talking with his therapist (Robin Williams), the two visit Wilfred, whom Ryan still sees as a man; Ryan also learns that Jenna and Drew have broken up. After a couple of visits, in which a wheelchair-bound Wilfred (handicapped due to his accident in the first season finale) and Ryan talk about why Ryan sees Wilfred as a man, Ryan's therapist ups his dosage of pills, and eventually tries to give Ryan electroshock therapy. Wilfred, in the disguise of a man (Brian Baumgartner), and Bear break Ryan out of the mental institution, only for Ryan to realize that the entire mental institution, and the events of the episode so far, are a daydream. Ryan actually has a new, boring corporate job, and the hallucinations he had been having periodically throughout the episode of sitting at a table with co-workers (Steven Weber, Rob Riggle, Allison Mack) and holding a tennis ball are actually his real-life job. Ryan gets up from the table and goes home, where he sees Jenna and Drew embracing, assumed to be still dating, outside of his house. Inside, Ryan goes to the closet, breaks through the wall, and finds the basement where he and Wilfred had hung out during the first season, but everything is boarded up and dusty. He finds Wilfred's will, a task he had been asked to do in the first season finale, which only says one sentence: "Keep digging," a metaphoric piece of advice to Ryan. Ryan then proceeds to clean up the basement, even getting out his bong and putting it on the table, hinting that he will continue to hang out with Wilfred.
Opening quote: "Discontent is the first necessity of progress." - Thomas Edison