请问如何恰当地运用表示同情的英文句子?:.

请问如何恰当地运用表示同情的英文句子?:.
以下表示同情的英文句子在什么情况下用:
1.I’m deeply sorry to learn about.
I’m most upset to hear about.
I’m sorry to hear that.
2.I feel tremendous sympathy for...
Please accept my deepest sympathies.(Very formal expression given to the sufferer.)
I really sympathize with you.
3.Oh!What a dreadful thing to happen!
4.You must be feeling very sad.
It must be tough for you.
It must be hard on you.
5.Poor thing!He must be feeling awful now.
6.Is there any way I can help?
7.I know how it feels!/ I know how you feel.
8.That’s too bad!/ That’s unfortunate.
9.That’s just awful!
10.How terrible!/ How awful!/ How sad!
11.What a pity!/ That’s pity!
12.It’s a sad thing./ What a sad thing!
13.Oh,that’s such hard luck!
以下的对话选以上那些句子补充最恰当?
A:I’m sick to my stomach.I feel vomiting.
B:__________________________________________.
2． A:Yesterday when I got to the theatre,the play had been over.
B:_______________________________________________.
3． A:The bank was robbed last night.
B:_______________________________________.
4． A:My house was burnt down (烧毁)in a big fire.
B:__________________________________________.
5． A:I have failed in the English final-exam.
B:_____________________________________________.

I’m sorry to hear that.
What a pity
That’s too bad!
I really sympathize with you.
It must be tough for you.