Questions convey information about the questioner, namely what one does not know. In this paper, we propose a novel approach to allow a learning agent to ask what it considers as tricky to predict, in the course of producing a final output. By analyzing when and what it asks, we can make our model more transparent and interpretable. We first develop this idea to propose a general framework of deep neural networks that can ask questions, which we call asking networks. A specific architecture and training process for an asking network is proposed for the task of colorization, which is an exemplar one-to-many task and thus a task where asking questions is helpful in performing the task accurately. Our results show that the model learns to generate meaningful questions, asks difficult questions first, and utilizes the provided hint more efficiently than baseline models. We conclude that the proposed asking framework makes the learning agent reveal its weaknesses, which poses a promising new direction in developing interpretable and interactive models.