[{"role": "user", "content": "I'm working on a personal memoir and I need to translate a poignant sentence into Italian - could you help me find the best way to express 'I used to be ugly' in Italian?"}, {"role": "assistant", "content": "The translation of 'I used to be ugly' in Italian is 'Io ero brutto.' This sentence conveys the idea that you didn't find yourself physically attractive in the past, but it's a poignant and honest expression of self-reflection."}]