"Pleasure Over Pain" by Al Jarreau tells the story of a past love that ended prematurely and the lingering feelings that the narrator continues to hold onto. The song captures the sentiment of longing and the willingness to endure heartbreak in order to experience the joy of love. The lyrics depict the narrator reminiscing about the moments they shared with their former lover during the autumn nights. They describe the longing and torment they feel in their absence, as they watch raindrops battling against a window pain. Despite feeling trapped and consumed by their love, they express a bittersweet nostalgia for the time they once had together. The chorus reflects on the past love as an "everlasting love" that ended prematurely. The feelings they had for their partner are likened to the scattered stars in the sky, symbolizing the lost potential for their relationship to shine and flourish. Despite the pain and heartbreak, the narrator finds themselves drawn back to their love, choosing to experience pleasure over the pain they endured. The lyrics also emphasize the regrets and missed opportunities the narrator feels. They express remorse for not expressing their feelings and making necessary moves when they had the chance. The song portrays the torment of their unfulfilled desires and a mind that refuses to forget. The narrator's heart is described as a butterfly trapped in their lover's net, revealing the tumult they experience as they struggle with their emotions. The song conveys the desperation of the narrator, praying for their former partner to change their mind and longing for a second chance. The lyrics question whether they have waited too long and express the conviction that if their love were to return, it would be everlasting. The narrator constantly finds themselves in this cycle of hope and despair, uncertain if their attempts to communicate are reaching their former partner or if they are simply wasting their time. Overall, "Pleasure Over Pain" by Al Jarreau explores the complexities of a lost love, the wistful longing for a second chance, and the struggle between the pleasure experienced in love and the pain endured when it ends prematurely.