In this article, we present a new perspective on how to combine inquiry-based, problem-oriented learning with practices in the Humanities. Our particular interest is how the initial phase of finding "the problem" can be undertaken in a conjoint way with students, that is in the form of inquiry-based learning where there are no pre-defined questions set by the teacher. Inspired by C. Wright Mills, we argue that "the imagination" is key to opening up inquiries into problems, for students and researchers alike. Through an outline of what we call "the Humanities imagination" we develop a set of heuristics for stimulating a turn from topics to problems in the context of the Humanities. We show how combining inquiry-based learning with the Humanities suggests both new pedagogical practices, new models (the teacher as interlocutor), and a new balancing of the ecology of the Humanities emphasizing its particular imaginary over its disciplines.