The Whether Man is the very first person Milo encounters in the Lands Beyond at the beginning of the book who says things multiple times and is sometimes mistaken for being the Weather Man. He lives in Expectations. He is voiced by Daws Butler in the movie version and flies all over the place with balloons with question words on them. Faintly Macabre is his sister. His job is to make people go beyond Expectations and predict whether or not there will be weather. Milo's conversation with the Whether Man gives a small example of just how wacky everybody else in the Lands Beyond is going to turn out to be. Even the Whether Man can't help twisting ordinary words around and giving them new meanings: "I'm the Whether Man, not the Weather Man, for after all it's more important to know whether there will be weather than what the weather will be". The Whether Man brings out the idea of uncertainty and he's the first of many characters to encourage Milo to get away from the end goal of just making sense.
- There is no weather in space, but on Earth there is always weather, therefore here there is no need to predict whether or not there will be weather. This suggests that either he is not making sense because Rhyme and Reason are missing, or this world works differently from our world.
- According to Earth physics, he would need 5,714 balloons to lift him up.
- He believes that knowing whether or not there will be any weather is more important than knowing what the weather will be.