[{"role": "user", "content": "I'm writing a story about a character named Tom and I want to describe his past appearance to my Italian readers, can you help me translate the sentence 'Tom used to be ugly' into Italian?"}, {"role": "assistant", "content": "The translation of 'Tom used to be ugly' in Italian is 'Tom era brutto.' This sentence accurately conveys that Tom was ugly in the past, and it's the perfect way to describe his previous appearance to your Italian readers."}]