Enigmas and riddles have been used in learning as a means for developing understanding and memory, being learning and amusing a winning binomial from classical time, used by rhetoricians in all times. Riddle collections are common in many cultures and traditions and their didactic value is often emphasized. Applying Pagis’s hypothesis to mythological kenning category, we could hypothesize an evolution/deconstruction of tales and legends into riddles, arguing that, once guessed, some riddles may have been transformed into poetical formulas. Therefore kennings present a conceptual base of similarity and contiguity and correspondences between domains do not depend on a similarity of attributes, but on a similarity of stereotyped associations or schemata. This parallel structure of correspondances is shared also by riddles. Since metaphors and metonymies (kenning constituent elements) play a key-role in guessing, remembering and communicating, this article indicates a teaching-learning role also for these tropes, traditionally seen as complicated and confusing.