Translation is more than the mechanical act of converting words from one language to another; it is the cultural, emotional and intellectual negotiation of meaning. Especially idioms, proverbs and culture-bound terms carry cultural history and social values that often do not exist in the target language. This creates linguistic and cultural gaps known as untranslatability. This paper examines the concept of untranslatability and the challenges faced while translating idioms, proverbs and culturally loaded expressions with focused examples from English–Hindi and English–Marathi language pairs. It further discusses existing translation strategies and argues that complete equivalence is often impossible; translators must act as cultural mediators who balance meaning, flavour and readability.