The lyrics talk about falling in love again after not expecting to. The singer ponders on the uncertainty of the situation, questioning how they will know if they are making the right decisions and how they will know if they are truly in love.

Meaning of "(How Will I Know) I'm Falling in Love Again" by Willie Nelson

The song reflects the vulnerability and uncertainty that comes with falling in love again after a past heartbreak or disappointment. The repetition of "How will I know" emphasizes the confusion and doubt that can accompany new romantic feelings. The lyrics suggest that the singer is afraid of making mistakes or getting hurt again, bringing up the question of how to navigate these emotions and make the right choices. It captures the hesitancy and fear of vulnerability that can arise when opening up to love after experiencing pain. Overall, the song portrays the internal struggle of balancing the desire for love with the fear of getting hurt again.