A filmmaker sets out to make a new project in order to figure out how he's screwed up every relationship he's ever had.
| Actor | Role |
|---|---|
 Elias KoteasJake Klein | Jake Klein |
 Jennifer Jason LeighSheryl | Sheryl |
 Virginia MadsenBeth | Beth |
 Jane SeymourJoanne | Joanne |
 Mike VogelActor Jake | Actor Jake |
 Gia MantegnaSarah | Sarah |
 Tanner BuchananSammy | Sammy |
 Liana LiberatoRain / Young Joanne | Rain / Young Joanne |
 Cynthia MurellPersephone | Persephone |
| LLauren LakeLaurie | Laurie |
 Shasi WellsVenus | Venus |
 Annie MonroeActor Jocelyn | Actor Jocelyn |
 Christina GranceAphrodite | Aphrodite |
 Kevin MilesCool Party Guy | Cool Party Guy |
| KKevin RailsbackYoung Jake | Young Jake |
 Ron GilbertMitch Klein | Mitch Klein |
| KKerry SteinGrandfather | Grandfather |
 Meredith SalengerMom | Mom |
 Susan TraylorJoceyln | Joceyln |
 Kelly PendygraftActor Beth | Actor Beth |
 Yetta GottesmanJ Date Woman | J Date Woman |
 Googy GressRichie Madden | Richie Madden |
 Mara LuthaneVera | Vera |
 Christian MadsenGrip | Grip |
| DDonna BryceActor Mom | Actor Mom |
| BBill BryceActor Dad | Actor Dad |
 Brooke NewtonSummer | Summer |
 Annie McCain EngmanCrafty | Crafty |
| JJason WeissParty Guest | Party Guest |
 Chris SpinelliParty Guest | Party Guest |