In the late 1990s, when Sonny seeks to redefine his long-term relationship with Chester, the painfully introverted cartoonist begins sleeping with sex workers and discovers an unexpected new form of intimacy.
| Actor | Role |
|---|---|
 Dan BeirneChester Brown | Chester Brown |
 Emily LêSonny Lee | Sonny Lee |
 Andrea WerhunDenise/Yulissa | Denise/Yulissa |
 Noah LamannaSuzo Jones | Suzo Jones |
 Chris SandifordCain | Cain |
 Ely HenryCecil | Cecil |
 Rebecca ApplebaumLaura | Laura |
 Ehren KassamMiles | Miles |
 Ishan DavéReed | Reed |
 Stephen KalynCarl | Carl |
| HHannia ChengAnne | Anne |
| JJamie WhitecrowAngelina | Angelina |
| LLisa SmolkinWendy | Wendy |
 Lea Rose SebastianisKitty | Kitty |
| DDusty LeeJolene | Jolene |
 Becky JohnsonTina | Tina |
| KKitoko MaiAmanda | Amanda |
| RRubie MagnitudeMandi Moulin | Mandi Moulin |
| TTanya CheexPatience | Patience |
| DDainty SmithCeline | Celine |
 Becca Willow MossJulie | Julie |
| DDot StarkeyOther Angelina | Other Angelina |
| DDesiree Das GuptaWoman on the Street | Woman on the Street |
 Sabrina SaudinHeidi | Heidi |
 Kris SiddiqiRick Wiggins | Rick Wiggins |
| CCappyMo | Mo |
 Connor SmithComic Fan | Comic Fan |
 Kaitlyn Chalmers-RizzatoCallie (voice) | Callie (voice) |
 Rodrigo Fernandez-StollMandi's husband | Mandi's husband |
 Willow AstburyMandi's daughter | Mandi's daughter |