The lyrics describe a situation where the narrator's partner is coming home late, clearly feeling guilty about something, and unable to meet the narrator's eyes. The narrator reflects on their own past mistakes and how they have seen the same guilty look in themselves many times.

Meaning of "I've Seen That Look On Me (A Thousand Times)" by George Strait

The song delves into themes of regret, mistakes, and forgiveness in relationships. The narrator acknowledges the flaws within themselves and how they have passed those on to their partner, teaching them how to cheat. Despite this, there is still love and a sense of understanding towards the partner's actions. The repetition of "I've seen that look on me a thousand times" highlights the cyclical nature of mistakes and how they tend to repeat themselves in different forms. Ultimately, the song explores the complexities of human behavior, secrets, and the difficulty of breaking patterns of betrayal.