[{"role": "user", "content": "I'm trying to learn some key phrases for an upcoming trip to Italy and I was wondering, how would you say 'You look doubtful' in Italian?"}, {"role": "assistant", "content": "The translation of 'You look doubtful' in Italian is 'Sembra dubbiosa.' If you're speaking to a male, you would use 'Sembra dubbioso.' But in your case, since 'You look doubtful' is referring to a female, 'Sembra dubbiosa' is the correct phrase to use."}]