気の毒･悲しい･かわいそう･同情･いたわる･お悔み

Sorry: 気の毒に思う

I feel sorry for him.

I'm sorry to hear that.

I'm sorry to hear about your job.

I'm sorry to hear that you lost your job.

Poor: かわいそう･気の毒な

Poor John.　かわいそうなジョン

Oh, poor thing! かわいそうに

Oh, you poor thing! かわいそうに

That's ...

That's too bad.

That's sad.

That's unfortunate.

Must Have Been: 同情を表す

(過去）It must have been hard/tough (for you).

(現在)  It must be hard/tough (for you). That's hard/tough, isn't it?

いたわる：上手くいくといいね・よくなりますように

I hope things get better (for you) soon.

I hope you feel better soon.

誰かが亡くなった時

condolence　　　必ず-sを付ける

loss  喪失･遺失

I'm very sorry to hear of your loss. Please accept my condolences.

I'm so sorry for your loss.

文語↓

Our thoughts are with you during this difficult time of loss.

Our thoughts and prayers are with you.

You are in my thoughts.

お悔みにひと言加える↓

Is there anything I can do for you?

Please let me know if there is anything I can do.

If there is anything I can do I'm here for you.

If you need anyone to talk to, I'm always here for you.

I will miss him/her.