In "Misery Loves Cabernet," the narrator reflects on their own romantic decisions by considering how they would advise their great-granddaughter regarding a man they currently find appealing. This introspection reveals a conflict between personal experience and ideal advice, as the narrator grapples with whether to encourage steadfastness or caution when it comes to this man's behavior towards her. The underlying question is about self-awareness and the irony of failing to follow one's own counsel.

The narrator's dilemma highlights the complexity of romantic relationships, where emotions often cloud judgment. By questioning why they don't take their own advice, it emphasizes the importance of recognizing red flags in love and the struggle between desire and self-respect. This narrative ultimately encourages readers to reflect on their own relationships and the wisdom they might ignore in favor of fleeting passion.