Expectations play a vital role in any part of life, not at least in educational practices. This paper discusses expectation in formal music education from a post-pragmatist, deleuzian perspective where expectation is considered neither solely social nor personal, but rather discursive. Music is considered a kind of aesthetic communication in the paper and different aspects of expectation are discussed in relation to music education. The term “possibilism”, borrowed from the Norwegian philosopher Næss plays an important role in understanding how music education should be concerned with training imagination and facilitate for a wider and richer set of expectations in order to help learners become interesting, aware, critical and happy affiliates of music.