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After their kiss, Jenna decides she needs a little distance from Ryan, as well as Wilfred. Meanwhile, Wilfred, who is convinced Jenna is cheating on Drew, tries to find the culprit.
Wilfred tries to organize a neighborhood watch in order to keep Jenna from installing a security system at their home.
Ryan realizes he isn't moving forward in his life. Meanwhile, Wilfred falls in love with the dog Ryan's roommate Anne is looking after.
Ryan seeks Bruce's help to get closer behind the secret of Wilfred's existence. However, Bruce asks for something in return and a game of double-crossing begins.
During Ryan's Christmas dinner for the whole Newman family, Wilfred finds a way to trigger a confrontation between them.
Ryan seeks the help of a therapist following his breakdown at a supermarket.
During a walk at night to fight off Ryan's insomnia, a neighbor's actions raises suspicion in Ryan and Wilfred.
Wilfred interrupts Ryan's efforts to organize Jenna's 30th birthday party in order to make him write a book about Wilfred's life.
When Ryan decides to rent out a room in his house to pay the mortgage, Wilfred uses the opportunity to get the perfect roommate.
In order to impress a woman, Ryan enrolls Wilfred in a dog training class.
His sister's new love interest raises Ryan's suspicion.
Ryan becomes friends with the mailman who happens to be Wilfred's enemy.
Wilfred and Ryan try to find Wilfred's original owner.