Is it impossible to imaginatively simulate what it’s like to be someone with a different gender experience – to understand them empathically? Or is it simply difficult, a challenge requiring effort and dedication? I first distinguish three different sorts of obstacle to empathic understanding that are sometimes discussed: Missing Ingredient problems, Awkward Combination Problems, and Inappropriate Background Problems. I then argue that, although all three should be taken seriously, there is no clear reason to think that any of them are (...) both genuinely intractable and also significant impediments to the kind of empathic understanding we might want. To that extent, the challenge to interpersonal understanding here may be more a matter of skill and work than a hard boundary. (shrink)