The song "Why Should I Cry" by Heather Headley is about a relationship that has turned sour. The narrator used to feel blessed to be loved by their partner but now regrets their decision to be with them because of the pain and heartache they have caused. They long for the love and affection they used to receive but their partner has become distant. The chorus repeats the question of why they should continue to stay and endure the pain. The narrator questions why their heart tells them to walk away but they stay regardless. They cry every day and pray for a solution to their problems. They need affection and therapy to get rid of the pain inside of them. The second verse suggests that the narrator is afraid to leave because they have been with their partner for so long. But they realize that it's time to dry their eyes and move on. They are unsure of what went wrong in their relationship but know that staying is no longer an option. Overall, "Why Should I Cry" is a song about a relationship that has reached its breaking point and the narrator's struggle to move on from it.
