The singer struggles with conflicting emotions towards Roxy, questioning whether he's right or wrong in his feelings. He recalls the intense connection they shared when they first met, leading to sleepless nights and deep regret. Despite the undeniable love he feels, there is a sense of sadness and mystery in Roxy's eyes that he cannot decipher.

Meaning of "In Roxy's Eyes" by Timothy B. Schmit

"In Roxy's Eyes" explores the complexity of emotions that come with infatuation and love. The singer is torn between the strong feelings he has for Roxy and the uncertainty of whether pursuing those feelings is the right choice. The reference to Roxy's eyes symbolizes the mystery and depth of her emotions, which the singer struggles to understand. The sleepless nights and regret highlight the internal conflict between following his heart and acknowledging the potential consequences of his actions. This song delves into the struggle of balancing passion with reason in matters of the heart, where intense emotions can cloud judgment and lead to a tumultuous inner journey.