Humor processing is quite an innovative area in intelligent agent technologies. In this chapter we present the results of our work on a multiagent joking conversational system, which is able to use humor during non-constrained conversations with humans, in reaction to their particular emotional states. Thus, this work combines the areas of humor processing, emotiveness analysis and dialogue agent technologies, being the first one to do so. We first describe the background of our study, including state of the art of research in the field of humor-equipped agents. We describe our multiagent system's general construction and algorithms of each constituent agent, i.e. a chatterbot, a humor generator and emotion detector. Two evaluation experiments: user-oriented and automatic, showed that the humor-equipped system was evaluated as more friendly, making users feel better and was generally more likable than a similar system without humor. These results are discussed and some ideas for the future are given.