The meaning of the lyrics of the song "(How Will I Know) I'm Falling in Love Again" by the artist "Willie Nelson"

Willie Nelson's song "(How Will I Know) I'm Falling in Love Again" explores the uncertainty and apprehension that come with falling in love again, especially after experiencing past heartbreak.

The lyrics depict the narrator's realization that he is falling in love, despite not expecting to. The line "Never thought I'd fall in love again" conveys his surprise and perhaps even a hint of fear towards vulnerability. He is unsure if it's wise to open himself up to someone new, especially since he doesn't know how it will turn out.

The line "Maybe I'm repeating all my mistakes" suggests a past negative experience with love. He fears that he might be falling into the same traps, repeating the same mistakes that led to pain before.

The chorus, "How will I know if I'm winning or losing," reflects his uncertainty about the future of this relationship. He doesn't know if it will bring him joy or lead to further heartache. The repetition of "how will I know" emphasizes his confusion and desire for an answer to this question.

Despite his doubts and fears, the narrator surrenders to his feelings. He acknowledges that he is "falling in love again," even though he doesn't know what the outcome will be. This encapsulates the song's central theme: love is a risk, and there's no way to know for sure if it will lead to happiness. All one can do is follow their heart and be prepared for whatever comes their way.