[{"role": "user", "content": "I'm having a hard time expressing my feelings to my Italian friend who recently lost someone, and I want to offer my condolences; how would I translate 'I miss Tom terribly' into Italian to let them know I'm thinking of them?"}, {"role": "assistant", "content": "I'm so sorry to hear that your friend is going through a tough time. To express your condolences and let them know you're thinking of them, you can translate 'I miss Tom terribly' to Italian as 'Mi manca terribilmente Tom.' This should help you convey your feelings and offer support during this difficult period."}]