This paper aims to analyse the spiritual transformation of the Dreamer/Narrator on his way from a sinful nature to divine virtue in medieval dream poem Pearl by the Gawain-poet. At the beginning of the poem, the bereaved dreamer is grieving for the loss of a girl, most probably his daughter and mourns for his lost “pearl”. He cannot comfort himself by any means and fails to surrender to the divine will as a consolation. As a typical aspect of the genre, the dreamer, then, sleeps and finds himself in a vision where he meets the “Pearl Maiden”. The maiden looks like his pearl, yet he notices that she has been transfigured. She marks that she lives blissfully as a queen in the New Jerusalem now as one of the brides of the Lamb. Through a theological argument, the Pearl Maiden intends to teach him divine values and make him abandon his worldly desires to which he is too loyal. After this peculiar experience, the dreamer wakes up and realizes that he is also transformed into a person who can now comfort his intense grieving by submitting himself to heavenly virtues. In this light, the paper examines the way the dreamer in Pearl changes his perspective from a penchant for worldly desires to a total heavenly conduct under the guidance of the Pearl Maiden.