The song "I Know How To Lose You" by John Hiatt is a heartfelt reflection on the speaker's past mistakes and failures in love. The lyrics reveal a sense of regret and self-awareness about their inability to maintain healthy relationships. The speaker acknowledges their history of losing love and admits that they don't know how to sustain a good thing. They have experienced the pain of losing someone they cared about and have walked away from a promising relationship in the past. They express that despite feeling lost and uncertain about finding love again, they are well acquainted with the process of losing someone. The song also touches upon the speaker's struggles with their own emotional state and self-destructive tendencies. The reference to leaving before dawn, without any words or tears shed, suggests a pattern of avoiding emotional confrontation. They find themselves wearing a facade of emptiness while out in the world, hiding their pain behind a smile and a tip of the hat. The line "You know the story, still I hope for myself" implies that despite being aware of their past mistakes and destructive behavior, the speaker still holds onto hope for finding love. However, they compare this hope to a gambler's expectation of great wealth, suggesting that it may be unrealistic or unlikely. The song portrays a sense of detachment and isolation, as the speaker observes how people on the street don't remember their former lover's name or recognize their pain. The speaker hints at their ability to hide their true emotions from others, putting on a brave face while dealing with the pain and loss. Overall, "I Know How To Lose You" showcases the internal struggles and reflections on love and loss. It explores the speaker's recognition of their destructive patterns and their uncertain hope for finding love again, while revealing the loneliness and emotional hiding they experience in the aftermath of failed relationships.
