the tool tells him to LAUGH at his jokes, and he laughs, and he expresses his shock at actually laughing "naturally" at something so unfunny.
Yeah, so would it work if The Tool told him to actually find the jokes funny?
maybe, the update with Ansom and Stanley would argue no... or maybe his duty compelled him to not relax but humor his overlord. AFAIK orders can only impact your physical actions and reactions, not how you feel about them
sex may boost unit production or improve stats based on the participants. (someone else said something similar on another thread, sorry for plagarism) Maybe Stanley should have Sizemore and Maggie to, cough, collaborate to increase caster pop rate. maybe get jack to fool around with wanda a little. maybe get all four to have the first four way caster link up