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my sympathies; that's too bad; my condolences
彼女の話を聞いてお気の毒に思った。
I felt sorry for her after hearing her story.
お気の毒に、事故で怪我をされたそうだ。
I'm sorry to hear you were injured in an accident.
病気の友人にお気の毒にと伝えてほしい。
Please tell my sick friend that I'm sorry.