German phrase
Das tut mir leid.
Meaning
I'm sorry to hear that
When to use it
Shows sympathy for bad news. It comforts someone after sad news.
Example dialogue
Ich habe meinen Job verloren.
I lost my job.
Das tut mir leid. Ich helfe dir gern bei der Jobsuche.
I'm sorry to hear that. I'll gladly help you look for a job.