AbstractTeaching machines to ask questions is an important yet challenging task. Most prior work focused on generating questions with fixed answers. As contents are highly limited by given answers, these questions are often not worth discussing. In this paper, we take the first step on teaching machines to ask open-answered questions from real-world news for open discussion (openQG). To generate high-qualified questions, effective ways for question evaluation are required. We take the perspective that the more answers a question receives, the better it is for open discussion, and analyze how language use affects the number of answers. Compared with other factors, e.g. topic and post time, linguistic factors keep our evaluation from being domain-specific. We carefully perform variable control on 11.5M questions from online forums to get a dataset, OQRanD, and further perform question analysis. Based on these conclusions, several models are built for question evaluation. For openQG task, we construct OQGenD, the first dataset as far as we know, and propose a model based on conditional generative adversarial networks and our question evaluation model. Experiments show that our model can generate questions with higher quality compared with commonly-used text generation methods.