The lyrics describe the journey of life as a winding road, where the narrator encounters different experiences and emotions. They hitch a ride with a showgirl, reflect on feeling alone, and question the reality of their past experiences. The song emphasizes the unpredictability of life and the constant pursuit of feeling fine.

Meaning of "Everyday Is a Winding Road" by Prince

"Everyday Is a Winding Road" by Prince delves into the complexities of life, showcasing its unpredictability and the constant changes and challenges that one faces on their journey. The repeated refrain of everyday being a winding road emphasizes the idea that life is not a straight path but a series of twists and turns. The encounter with the showgirl represents meeting different people along the way, each with their own stories and experiences. The mention of feeling alone and questioning the reality of past experiences highlights the introspective nature of the song, where the narrator grapples with existential questions and the meaning of their own existence. The lyrics ultimately convey a sense of resilience and perseverance in the face of life's uncertainties, offering a message of hope and determination to keep moving forward towards feeling fine.