Meaning of "Highway" by Ingrid Michaelson

The lyrics of "Highway" express the bittersweet emotions that come with watching a loved one, likely a child, grow up and become independent. The singer reminisces about the past seventeen years, highlighting the rapid passage of time and the changes that have occurred in their relationship. The mention of the baby's birth weight and how their hands have grown larger than the singer's serves as a metaphor for the child's physical and emotional growth. The repetition of "I'm regretting letting you fly" conveys the singer's feelings of nostalgia and longing for the past, mixed with a sense of guilt or regret for not being able to hold onto those precious moments forever. Overall, the song captures the universal experience of parents watching their children grow up and move on, while grappling with mixed emotions of pride, love, and a longing to hold onto the past.