Help me, guys. A Russian friend's grandmother just died, and I am not 100% sure of how to express my condolences properly. I want to say that I am deeply sorry, but I am very sure that извини or прошу прошение applies to the speaker making a mistake, when in this context I am not asking for forgiveness. I reckon that мне очень жаль would be more correct, but how can I specifically say, "I am deeply sorry for your loss"? First give me a generic expression, then give me others that may more sincere in expressing sorrow for the death of a loved one. Given the sensitive nature of what I am saying, please give specific meaning (connotation, tone, etc.) to what you offer so I will not make a mistake in tone, which must perfectly match what I am trying to convey. Спасибо, ребята!