Standup comic Craig Shoemaker tells the therapist stories of his failed relationships with women (dates, wife etc.)
| Actor | Role |
|---|---|
 George WendtTherapist | Therapist |
 Craig ShoemakerCraig | Craig |
 Courtney Thorne-SmithDeb | Deb |
 Farrah FawcettCraig's Dream Date | Craig's Dream Date |
 Rob SteinbergSteiny | Steiny |
| EEsther AuerbachNana | Nana |
 Harley Jane KozakKaren | Karen |
 Karen LorreMarle | Marle |
 Charlie TalbertNot listed | Not listed |
 Gina GarciaNot listed | Not listed |
| AAndrew StarnesNot listed | Not listed |
 Amanda KielyGirl on beach | Girl on beach |
| KKyle ThomasNot listed | Not listed |
| MMay QuigleyNot listed | Not listed |
| BBrian WagnerNot listed | Not listed |
| KKurt RambisKurt | Kurt |
| BBob FonsecaNot listed | Not listed |
| DDale DudleyBasketball Player | Basketball Player |
| RRick SingerNot listed | Not listed |
| RRobert D. NovakNot listed | Not listed |
| TTony MoreheadNot listed | Not listed |
| BBobby BrewerNot listed | Not listed |
| GGabrielle BeimfordNot listed | Not listed |
| DDebra ColeNot listed | Not listed |