[{"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 say 'A me manca terribilmente Tom.' This translates to 'I miss Tom terribly' and conveys your feelings of loss and sympathy."}]