When Jeannie's baby sister goes on a date with Dave, Jeannie and Jim are determined to follow them and spy on the couple.

When Jim mixes up a drawing with a school application, he and Jeannie hope that the mistake goes unnoticed.

Funnyman Jim explores his struggle to juggle his family, his career, and his food. Plus, he deals with the difficulties that come with being a father.

Jim tries to stop eating junk food and is then faced with his greatest challenge: a child's birthday cake; Dave is hung over and goes with Jim to a kid's birthday party, where he is mistaken as a homeless man.

Jim plans a romantic anniversary that includes a Broadway show and a hotel stay, but the night is interrupted.

Jim and Jeannie agree to dine with Daniel and his father in order to act as buffers; Dave joins the group for a wild night.