In season 1, Jeff begins to push back against the limits of the well-oiled machine that is Mr. Pickles’ Puppet Time. Seb begins preparing the show for a life after Jeff. Deirdre grapples with her own personal and professional life issues.
Jeff Pickles decides it's time to talk about death on Mr. Pickles' Puppet Time. His executive producer, Seb, warns him that Mr. Pickles the persona and Jeff Pickles the person need to remain separate. Deirdre punishes her daughter Maddy for not eating her veggies.
Jeff makes a rash decision that could affect the ability of the show to continue. Seb strategizes how to rebuild Jeff's image. The two disagree about how Jeff can repair his family. Deirdre tries to learn more about what's happening while Maddy is at her piano lesson. Jeff's son Will decides to let loose with his new friends.
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.