Increasingly, humans communicate through technological devices, such as mobile phones and tablet PC’s. Insights from interpersonal communication are important for developing communication technologies. Certain communication technologies use these insights to mimic elements of human interpersonal communication, or even completely replace the human partner in conversational exchanges. With these developments, computer-mediated communication (CMC) is moving toward human-computer interaction (HCI). At the same time, with increasing knowledge about interpersonal communication and technological advances, HCI is becoming more social and moving toward CMC. Individuals respond socially toward computers. Humans, even experienced computer users, are inclined to treat their computers as largely natural and social and they tend to interact with their computers in affective ways. Nowadays, embodied computers are designed as socially interactive robots. They are not only technological supplementary tools for labor-intensive or hazardous tasks anymore, but gradually become part of our daily lives, fulfilling roles as, for example, pets, nurses, office assistants, tour guides, teachers, and even emotional companions (e.g., Sony’s AIBO robot dog, or MIT’s Kismet). A salient aspect of humanness in robots is the expression of emotions. However, compared to human affective complexity, affective communication of contemporary software agents and robots is still quite simple. The original Turing-Test is text-based but we enriched the communication by applying a virtual human in graphical format, called Tom, capable of speech and facial expressions. Because in mediated interpersonal communication emotions play a salient role, Tom’s communications were affect-laden. Our Turing test took the form of a speed-dating session in which we tested the performance of our Silicon Coppélia software. Female participants were randomly assigned to the virtual human Tom, who was either controlled by our software (HCI) or by a human confederate (CMC). In either case, participants were told that they interacted with a robot to see whether human performance could outdo that idea. Tom could give verbal as well as nonverbal cues. Results obtained with Bayesian structural equation modeling revealed that, even in an enriched version of the classic Turing-Test, participants did not detect differences between the two versions of Tom, which is a nice tribute to the Turing Centenary of this year. Participants did not recognize significant differences in the cognitive-affective structure underlying the emotional behavior produced by our Silicon Coppélia software and that produced by human confederates. We can conclude, as far as the testing capabilities of this experiment go, that we created a humanoid simulation of affect so natural that young women could not discern dating a robot from dating a man.