Drawing upon Nel Noddings' contention that, if children are to be happy in schools, their teachers should also be happy, this paper tries to explore a way in which the obviously intimate but seemingly conflicting connections between students' and teachers' happiness can be understood from the viewpoint of Stanley Cavell's reading of J. S. Mill. Mill's conceptions of desire and pleasure are examined as a means of liberating the above connection from existing prioritization: that is, teachers' or students' happiness comes first. The pursuit of happiness for both teachers and students is discussed, in the hopes of illuminating alternative images of teacher education.