Meaning of "Winona" by Matthew Sweet

The lyrics of "Winona" by Matthew Sweet reflect the internal turmoil of the speaker as he grapples with feelings of loneliness and longing for someone he doesn't truly know. The repeated attempts to connect with Winona through a phone call symbolize his desire for communication and connection. The ambiguity of their relationship is highlighted by his conflicting emotions – wanting to keep things from her yet hoping she'll understand. The references to Winona as a movie star or long-lost girl suggest that she is idealized in his mind, representing an unattainable fantasy. The speaker's confusion between what he wants and what he truly needs underscores the complexities of human emotions and relationships. Ultimately, the song captures the universal experience of yearning for connection while navigating the uncertainties of human connection and understanding.