Surprising videos, e.g., funny clips, creative performances, or visual illusions, attract significant attention. Enjoyment of these videos is not simply a response to visual stimuli; rather, it hinges on the human capacity to understand (and appreciate) commonsense violations depicted in these videos. We introduce FunQA, a challenging video question-answering (QA) dataset specifically designed to evaluate and enhance the depth of video reasoning based on counter-intuitive and fun videos. Unlike most video QA clips, spanning a total of 24 video hours. Moreover, we propose FunMentor, an agent designed for Vision-Language Models (VLMs) that uses multi-turn dialogues to enhance models’ understanding of counter-intuitiveness. Extensive experiments with existing VLMs demonstrate the effectiveness of FunMentor and reveal significant performance gaps for the FunQA videos across spatial-temporal reasoning, visual-centered reasoning, and free-text generation.