The song "When Did You Know" by Jamie O'Neal is about a failed relationship where one person realizes that the other never truly loved them. The lyrics describe the moment when the protagonist realizes that their partner was only playing with their emotions and was not serious about a committed relationship. The song begins by recounting a time when the couple was happy and in love, but the protagonist later realizes that the relationship was never going to last. The lyrics express confusion and hurt as the protagonist struggles to understand why their partner would lead them on. The chorus of the song repeats the question "When did you know it wasn't love, when did you know it wasn't me?" as the protagonist tries to understand when their partner stopped caring about them. Overall, "When Did You Know" is a poignant exploration of heartbreak and the pain of realizing that a relationship is not meant to be. It emphasizes the importance of honesty and sincerity in any relationship, and the consequences of leading someone on with false promises.