Fairy tales have often been controversial, and today much of the controversy appears to revolve around gender issues. With a focus on gendered appearances and relationships, this article examines Hans Christian Andersen’s ‘Tommelise’ and ‘The Snow-Queen’ as well as Adventures in Fairyland (1853), a book of fairy tales written by one of Andersen’s admirers and promoters in nineteenth-century USA, Richard Henry Stoddard. Depictions of female characters in these tales are varied, with protagonists not always adhering to the feminine beauty ideal. The portrayal of both girls and boys are sometimes influenced by the notion of the Romantic child, which seems to tone down gender differences in descriptions of characters. Some of Stoddard’s fairy tales have a masculinist bias, but on the other hand his tales often go beyond the happily-ever-after ending. Indeed, a few of his fairy tales are remarkably explicit about adult erotic love, physical attraction, and sexual desire. So, when viewed through the lens of gender, both Andersen’s and Stoddard’s nineteenth-century literary fairy tales offer a twenty-first-century reader quite a few surprises and much food for thought and discussion.