The positive effect of humor can be increased through the delivery of user-personalized humor in naturalistic settings. In AGENTS, psychological models of humor and its’ everyday functions will be of use when attempting to create a top-down approach of humor that can be modeled to match each user’s preferences, fostering more natural and positive interactions with users. The end-goal of this process will be the implementation of user personalized humoristic interactions in the context of a multi-party interaction scenario with a card game involving more than one human and more than one robot. This is expected to lead to better interaction outcomes and increase the value perception of the robot, by contributing to greater user’s task enjoyment, engagement, and positive emotions.