Giving bad news: I'm afraid I've got some bad news for you…
I'm so sorry but…
I'm sorry to have to tell you that …
I know this isn't what you want to hear but…
I'm afraid to inform you of …
It is my unfortunate duty to tell you that …
I really feel bad to have to say this, but …
I really don't know how to say it, but …
Responding to bad news:
I'm sorry to hear that…
You must be feeling terrible …
That's awful!
Too bad!
Poor you!
Please, accept my deepest sympathy.
Anytime you need to talk, just call me …
If there's anything I can do, just let me know…
