The song "Why Now" by Wynonna Judd explores the theme of second chances in love and the struggles that come with it. The lyrics depict a scenario where the narrator's former lover returns after a long absence, saying all the right things and trying to win them back. The opening lines suggest that the lover had become a distant memory, almost like a dream. However, they have now reappeared in the narrator's life, seemingly realizing their mistake and wanting another chance. The chorus questions why they should let them back into their life after all the time they spent apart and the pain they endured. The narrator reflects on the past, mentioning that they had tried to forget everything and move on but hadn't been able to. Despite the pain and heartbreak caused by the previous relationship, the prospect of being with the person they still have feelings for seems almost worth it. They admit that the pain would be worth it just to have that connection and look into their eyes once again. The narrator implies that the former lover never truly understood or appreciated their efforts during the relationship, only realizing their mistake once they were gone. The repetition of the chorus emphasizes the hesitation and internal conflict the narrator feels about whether or not to give this person a second chance. The bridge questions the expectation that the narrator would wait for their former lover indefinitely. It implies a sense of frustration and refusal to be constantly available for reconciliation. Overall, "Why Now" explores the emotions and doubts that arise when faced with the possibility of reconnecting with a past love. It delves into the complex dynamics of love, the need for closure, and the fear of being hurt again.