Artificial intelligence modules can easily hold and interpret massive amounts of data, but are deficient re: nuanced human-humor. The design of this experiment was to create an operating system that understood the classic “joke” known as “That’s What She Said,” (identified in this paper as TARGET/TWSS), which is DEFINED as a sentence without human-sexual content that may be interpreted out of purported context as having sexual implications to the human-listener. The METHOD involved the downloading onto the operating system of episodes of televised humor show The Office with automatic instructions to search for the sentence “That’s what she said,” and its immediate antecedent. The CONTROL was the televised Lifetime documentary From Oxford to Meth, in which no TWSSs or antecedents can be found. The RESULTS included the ability of the operating system to identify the objective TWSS quality of any sentence, for example: “I stayed until it got hard” received a TWSS Score of +6, while “She biked to work” received a TWSS Score of -5. “Meth destroyed this family” got a TWSS Score of +2. The IMPLICATIONS of this successfully-performed experiment are inexhaustible: a Microsoft Word application with the ability to identify a good TWSS as one is typing and sonically alert the writer to this fact with a loud, pre-programmed “That’s what she said”; a TWSS-generating program that can provide up to 2,000 TWSS set-ups per second (and accompanying iPhone/iPad app); and a robotic TWSS-buddy, who follows one around, saying, “That’s what she said,” whenever the moment arises. Dr. Cnutsen and I are confident that this operating system has made great gains in bridging “robot-human-sex-joke-gap,” with eternal, widespread benefits to both technology and the future of man.