"Desmond's Big Day Out": Charlie and Pim try to cheer up a suicidal man named Desmond. At the office, Alan's hunt for his cheese takes him into the crawl space.
"Mr. Frog": Famous celebrity Mr. Frog's reputation takes a downward spiral due to his violent behavior, leading the Smiling Friends to rebuild his public image. Meanwhile Glep auditions to become the replacement Mr. Frog.
"Shrimp's Odyssey": Charlie and Pim have their own ways of helping Shrimp. Charlie attempts to improve his life while Pim tries to get his ex-girlfriend to reconcile with him. While this goes on, watchers across the country cast their vote on whether to introduce a new Smiling Friend to the roster — Smormu!
"A Silly Halloween Special": The Smiling Friends hold their annual Halloween party. Pim is tasked by The Boss to gather firewood at the nearby forest but gets lost and hunted down by a demonic entity.
"Who Violently Murdered Simon S. Salty?": Charlie and Pim visit the local fast food joint Salty's. When the owner, Salty, is murdered, any one of the talking mascots are a suspect.
"Enchanted Forest": The Smiling Friends are requested to help the Princess of the Enchanted Forest smile but end up lost in the Enchanted Forest and needing help from a strange man named Mip.
"Frowning Friends": The Smiling Friends get a direct competitor with the new business in town, the Frowning Friends, that makes everyone in town upset.
"Charlie Dies and Doesn't Come Back": On Christmas Eve, The Boss' request for a Christmas Tree ends up killing Charlie and sending him to Hell, which has literally frozen over after Satan becomes depressed with his job.
