The phrase "when pretty isn't pretty enough" often reflects moments or situations where external appearance or superficial beauty fails to satisfy deeper needs or expectations. It can relate to themes like self-acceptance, societal standards, or the limits of aesthetics. If you’re referencing this phrase from a specific poem, song, book, or cultural context, could you please clarify? That way I can provide a more tailored explanation or analysis. Otherwise, I can share interpretations or explore the idea in various contexts.