Wilfred begins to feel betrayed by Ryan when he decides to befriend the mailman, so the sensitive canine does everything he can to prove to his friend that the stranger that visits the home nearly every day is not to be trusted.

Ryan is unable to shake off his distrust for the new man in Kristen's life, which results in a number of strange encounters between the two men as they attempt to get to know each other for the sake of the woman in their lives.

Ryan begrudgingly agrees to team up with Wilfred to find a worthy birthday present for Jenna, which results in the two delving into questionable territory to ensure they get her the best possible gift.

With a forceful push from Wilfred, Ryan goes on a sudden crime-fighting spree around town due to a fit of sleeplessness that has him making drastic decisions that put his safety and questionable sanity in extreme jeopardy.

Ryan decides to turn to progressive psychotherapy to better understand a past trauma that has haunted him his entire life, but he finds that the revolutionary new method is not quite what he hoped for.