This research paper explores the application of John Bowlby’s Attachment Theory to William Shakespeare's sonnet, "Shall I Compare Thee." By combining a literary analysis approach with insights from psychology, the study seeks to uncover the emotional bonds and attachment dynamics within the sonnet. Through the identification and classification of attachment styles using Bowlby’s framework, the research examines how these styles influence the relationships between characters and contribute to the complexities presented in the sonnet. Additionally, the study investigates contemporary readers' emotional engagement with the text by exploring potential correlations between attachment styles and reader perceptions. The significance of this research lies in its unique integration of psychological theory within literary analysis, opening avenues for further exploration of attachment dynamics in classical literature. This interdisciplinary approach bridges the gap between psychology and literature, enhancing our understanding of attachment theory and its application in understanding human connections and emotions depicted in literary works.