Oh I’m so sorry to hear that!
That’s so disappointing!
That’s awful! I hope things get better soon.
That must have been terrible/awful!
You must be feeling terrible/awful!
I heard about….; I’m very sorry to hear about it.
I heard about…..; you must be having a hard time!
I heard about…; it must be really hard for you.
I’m very sorry to hear about…; please let me know if I can help with anything.
I’m very sorry to hear about…; is there anything I can do to help?
I’m very sorry to hear about…; if you want to talk about it, just give me a call.