The song "Here's That Rainy Day" by Astrud Gilberto reflects on the feeling of disappointment and heartbreak. The lyrics talk about the regret of not saving dreams and wishes for a rainy day, and how love can turn into a cold and lonely experience. The rainy day symbolizes the sadness and despair that comes with lost love. The song captures the feeling of longing for someone who is no longer there, and the realization that love can sometimes bring pain and loneliness. The lyrics express a sense of resignation and acceptance of the melancholy of a rainy day, mirroring the feeling of sadness and regret in love and life. Overall, the song conveys the message that love can sometimes bring about unexpected pain and disappointment, and the rainy day serves as a metaphor for the sadness that comes with it.