The lyrics express the singer's confusion over why they should cry, sigh, or feel blue over someone who left them alone and broke their heart. The singer questions the value of their love that was seemingly wasted on someone who hurt them, ultimately conveying a sense of resignation and acceptance.

Meaning of "Why Should I Cry Over You" by Frank Sinatra

The lyrics of "Why Should I Cry Over You" by Frank Sinatra reflect the internal struggle of someone grappling with the aftermath of heartbreak. The singer's initial confusion over why they should feel sad or upset over the person who hurt them speaks to the universal experience of trying to rationalize emotions in the face of betrayal. Despite the pain inflicted by the other person, the singer acknowledges that time spent loving them wasn't all in vain, as it was a sincere and genuine investment of emotion. The line "Someday your heart will be broken like mine" conveys a sense of eventual karma or cosmic balance, suggesting that the person who caused the heartbreak will one day experience the same pain. This sentiment can be interpreted as a form of emotional release and closure for the singer, allowing them to move on from the hurt and find solace in the idea of eventual justice. Overall, the lyrics capture the complexities of heartbreak, acceptance, and the eventual journey towards healing and self-realization.