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.