Shakespeare’s works have always been regarded to be the enigmas of the English literature. Although almost all his works are enigmatic, some of his plays like Hamlet and his sonnets seem to be more controversial. A review of the history of critical approaches to the Bard shows that there is an aspect of his works, particularly his sonnets, which has always been ignored by the critics. A reading of the sonnets in the light of de Man’s deconstructive method reveals the mystery to some extent. Paul de Man is one of the most influential critics of the Yale School of deconstruction. Applying his approach to the sonnets shows that they are self-deconstructive. In this article we try to delve into the domain of the sonnets, particularly the procreation sonnets with a de Mannian approach to reveal this quality.