The narrator contemplates the idea of never thinking about a woman in order to avoid missing her, but realizes that this approach would mean missing out on all the joys and complications of love and relationships. The repetition of "the trouble with never is never never works" emphasizes the futility of trying to avoid feeling emotions.

Meaning of "Trouble With Never" by Tim McGraw

In these lyrics, the artist reflects on the struggle between the desire for freedom and the yearning for love and connection. The narrator grapples with the idea of avoiding emotional entanglements to stay care-free, but acknowledges that the depth and intensity of his feelings for this particular woman make it impossible to stick to this plan. The internal conflict is rooted in the fear of vulnerability and commitment, juxtaposed with the overwhelming attraction and emotional pull towards the woman. By repeating the phrase "the trouble with never is never never works", the artist highlights the unavoidable nature of emotions and relationships, suggesting that trying to shut oneself off from feeling is ultimately futile. The lyrics convey a universal struggle between the desire for independence and the longing for deep connections, underscoring the complexities of human emotions and the inevitability of entanglement in matters of the heart.