"Waterproof Mascara" by Sheryl Crow explores the struggles of a single mother trying to protect her son from heartache and disappointment, while also dealing with her own emotional scars from past relationships.

Meaning of "Waterproof Mascara" by Sheryl Crow

The song delves into the complex emotions and responsibilities faced by single mothers, addressing the desire to shield their children from pain while grappling with their own vulnerabilities. The lyrics convey the mother's deep concern for her son, exemplified by her reluctance to introduce him to new relationships for fear of him getting hurt. The mention of waterproof mascara symbolizes the need to hide tears and emotions behind a façade of strength, underscoring the theme of resilience and protection. Through poignant reflections on love, loss, and parenthood, the song underscores the sacrifices and challenges faced by single parents, highlighting the importance of strength, love, and perseverance in raising a child in a broken relationship.