Ryan attempts to have a dinner party with Jenna, Drew, and his co-worker, Amanda, whom he begins dating.

Amanda appears odd around Wilfred, and after Wilfred and Bear ruin the dinner party, Amanda reveals that she discovered her Grandfather's two dogs consuming his deceased body, causing her fear of dogs.

After several weeks of dating, Ryan tells Amanda that he loves her, and they decide to move in together.

Afterwards, the company that Ryan works for loses all its investors, and his boss commits suicide.

Ryan and his mother go on a road-trip, against her doctor's orders, after her cat, Mittens, passes away.

Jenna's career becomes a joke after her freak-out on live TV goes viral, and Wilfred finally convinces Ryan to come clean to her.

Meanwhile, when Wilfred becomes jealous of the attention Jenna gives to the other neighborhood dogs, he accidentally pushes Drew's hunting shotgun over, which shoots Drew in the leg, days before his and Jenna's wedding, and Ryan offers to host the ceremony in his backyard for them.

An impromptu road trip leaves Wilfred, Ryan and his family in peril.

Wilfred and Ryan are confronted by shocking existential questions about life and love.