In this paper we explore how future smart environments can be given a sense of humor. Humor requires smartness. Entering witty remarks in a conversation requires understanding of the conversation, the conversational partner, the context and the history of the conversation. We can try to model interaction smartness and how to use it in creating not only witty remarks, but also to create humorous events. Smart sensors and actuators, embedded in our environments and our wearables allow us to make changes to a digitally enhanced physical environment. Witty remarks in language can have their counterpart in witty events in digital environments, including social media environments with their own communication characteristics. Sequential and parallel juxtapositions of incongruous and contrasting events invade our communication and, in addition, can be expected to emerge or to be created in digitally enhanced physical environments too, accidentally and intentionally.