How will learning “look” in the future? Everyone learns–and we do so in a creative and emotional way. However, learners’ creativity and emotions are often not explicitly included in the design process when exploring how technology can be used to provide new learning opportunities, which could result in shallow learning. One way to support such learning with technology could be playfulness. The current paper reports on some of our ongoing experiences in recent years using a playful design perspective to develop three educational Artificial Intelligence (AI) prototypes. Tackling applications intended to facilitate freedom, ease, and engagement in learning, the prototypes comprise an intelligent tutoring system, an automatic display tool, and a hand-waving detector. In closing, some lessons learned are shared to inform subsequent designs.