Jeff tries to fix his heartbreak. Deirdre deals with her daughter’s developing medical condition. Seb outlines the future of Mr. Pickles’ Puppet Time without Jeff. Jeff tries to get Will off pot by giving him a hobby.

Jeff deals with a one-night stand. Jill learns that Jeff has been sending money to someone behind her back and confronts him.

Jeff decides to step out of his comfort zone. Seb tries to get Jeff on board with new changes for Puppet Time, as well as his ice skating show – Pickles On Ice, starring Tara Lipinski.

Will tries to honor his brother in a unique way. Jeff decides to make some changes to Pickles on Ice. Deirdre lets her anger out on Maddy. Jeff tries to convince Vivian to continue with her treatment.

Jeff goes off script and starts to speak more honestly to children on Puppet Time as Seb panics that Jeff will soon have to appear on live television for the National Tree Lighting Ceremony. Deirdre and Scott get a new visitor from Japan – Mr. Pickles-San. The Pickles have Thanksgiving as a family.

Jeff meets the son of his pen pal, an inmate on death row, and decides to help him.

Jeff wonders if he’s having a breakdown or a breakthrough. Will gets into trouble at school. Scott confronts Deirdre about her feelings for Mr. Pickles-San. Seb decides to make a last-minute change to Pickles on Ice while Jeff is away.

Everyone in Jeff’s life deals with the results of the speech Jeff made on national television.