In this post we discuss the evolution of the relationship we have with our computational companions, and look to better understand the application of emotional sensing technologies. Having an interest in the intersection of design and artificial intelligence exposes you to a lot of interesting concepts and tools that seem appealing and relevant at first glance, but it is only when you start working with them you start asking deeper and more meaningful questions about their application and value to the end user. This was the case with emotional sensing technologies, like those offered by the popular emotional recognition service provider Affectiva, which offers tools for recognizing the user’s emotion based on a image of their face. As a technologist, you are first attracted by the how and it’s only after you become comfortable with the intricate details of it’s inner workings that you start questioning the why. It was only after having learned and made systems that could satisfactorily classify emotion given some text or an image of a face, that I started questioning how these could be applied. It is only recently that I have realized their significance and applicability; this realization is the starting point of this post. The concept of the computer was devised in the 19th century by an English mathematics professor named Charles Babbage; this concept was appropriately named the Analytical Engine, highlighting its purpose of performing and outputting mathematical calculations. This concept was finally realized around 1943 and found application in the area of trajectory calculations for military purposes. Users tended to be highly trained professionals who would interact with the computer using punchcards detailing explicit instructions for the computer to follow. An exploratory study of human-computer relationships is reported which utilizes gaming techniques. Attention is given to the conceptualization and measurement of human reactions and interactions; an attempt is made to investigate differentials between human-human and human-computer relationships.