In my dissertation, I develop a novel approach to thought experiments and literary learning. It’s novel primarily because, unlike many prominent approaches, it has us refrain from advancing theories, from giving logical analyses, and from explicating. We are, instead, to proceed in a way inspired by Wittgenstein’s writings. We are, that is, to clarify words that give rise to problems and to clear those problems away. To clarify words, we may compare language games in which figure terms like “thought experiment.” (...) Thereby, we might see that the concept these terms express has a family resemblance character. To clear away problems, we may describe how such a concept, if not illuminated, yields philosophical problems about thought experiments and literary learning. -/- After I develop this approach, I bring it to bear on two problems, and I achieve two main results. One problem concerns the nature of thought experiments. It is: Why do we have trouble explaining what we know them to be? I find that, despite appearances, we have no such trouble. Central to this result are two claims about thought experiments. One is that imaginings aren’t common to them. The other is that our unreflective concept of them has a family resemblance character. -/- The other problem concerns stories in works of literary fiction. It is: How could we possibly learn about the world from them? To solve it, you might claim that we learn by performing thought experiments, and then appeal to a theory of them. I find that you’d risk explaining the wrong thing. That is, you may well explain only how we learn—not how we do so from literature itself. Central to this result are three claims, which concern how these stories differ from thought experiments. They differ, I claim, (i) in how we count imaginings as experiences of them, (ii) in how free we are to interpret them, and (iii) in how complex they may be. This done, I’ve twice taken my novel approach and achieved results. (shrink)