There are different ways in which imaginings can involve the first-person. I can imagine skiing down a mountain, looking down the slope, the wind whipping me in the face. I can also imagine myself skiing down a mountain from the outside, adopting the point of view of a spectator watching myself fly down the mountain. I can also imagine that I am someone else entirely, say Angela Merkel, skiing down a mountain. How can we best characterize the content of such first-person imaginings? I look at two existing accounts: one proposed by Francois Recanati (2007a, 2007b) and the other proposed by Dilip Ninan (2008). I will argue that, although I think Recanati is correct in adopting a property-based theory of the content of certain first-person imaginings, the account lacks the resources to model the rich and distinct types of first-person imaginings that we can have. I then turn to Ninan’s (2008) account which makes substantial progress and contains a number of insights essential to characterizing the content of imagination, but I argue it misconstrues the imagining from the inside vs. imagining from the outside distinction and conflates the content of distinct imaginings. I then propose a new account that re-construes the imagining from the inside vs. imagining from the outside distinction and is able to accommodate the various ways in which imaginings involve the first-person.