Vendler’s :161–173, 1979) puzzle about imagination is that the sentences ‘Imagine swimming in that water’ and ‘Imagine yourself swimming in that water’ seem at once semantically different and semantically the same. They seem semantically different, since the first requires you to imagine ’from the inside’, while the second allows you to imagine ’from the outside.’ They seem semantically the same, since despite superficial dissimilarity, there is good reason to think that they are syntactically and lexically identical. This paper sets out the puzzle and offers a novel solution. Our proposal is that, just as there is knowledge-wh, there is also imagining-wh and that the inside/outside distinction Vendler points to is properly understood as a distinction within imagining-wh. In particular, to imagine swimming from the inside is to imagine what it feels like to swim, while to imagine swimming from the outside is to imagine what it looks like to swim. We show that this proposal is well grounded in both the semantics and syntax of ‘imagine.’ We also argue it makes better sense than its rivals of the data Vendler found so puzzling.