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I have been wondering, reading online and discussing with friends over this German expression for a long time.
I want to know if German speakers, Austrian males especially, feel that by saying "Es tut mir leid" they are expressing guilt and apologizing for a mistake they made.
Is that its only meaning?
Or can it also be used to express with empathy that you are sorry about something that is ABSOLUTELY not your fault? (by that I mean the "I'm sorry" we use in English such as "I am sorry you had a bad day" or "I'm sorry for your loss").

I am wondering if you feel you could react to the following situations by saying "Es tut mir leid, dass..." to express empathy and feelings of understanding towards another person, who might feel sad, angry, frustrated etc...

• Someone's grandma dies, you go to visit the person --> "Es tut mir leid, dass du traurig bist" or "Es tut mir für dich und deine Familie leid"




• Your girlfriend is sad because she had a bad day --> "Es tut mir leid, dass du einen schlechten Tag gehabt hast."




• A friend is down because he was criticized at work and has just told you --> "Es tut mir leid, dass es passiert ist"




• Your sister lost her connecting flight and calls you to complain and express frustration --> "Es tut mir leid, was passiert ist"




• A friend did not pass the most important exam of his Bachelor's degree and now has to wait a year to take the same exam again --> "Es tut mir sehr leid, dass du Pech gehabt hast".

If these expressions are not appropriate would you please let me know what kind of expressions could be used in German to react to them with empathy and understanding?

I want to be able to express feelings in German but I am seriously having a hard time finding the right way.

Short answer:
Yes, just like the English I'm sorry you can use es tut mir leid both for apologizing for something that is your fault and for expressing empathy.

Long answer:

Everyone of your examples is a valid way to express empathy in such a case. There are, however, other possibilities that might - in some cases - be more idiomatically.

In general, when someone tells you about his or her mishap or tragedy, Germans will often react quite automatically with

Oh, das tut mir leid.

(Oh, I'm sorry for that)

A variant of that would be

Tut mir leid, das zu hören

(I'm sorry to hear that)

It might be a regional thing, but I would connect the latter wording to situations where someone is disappointed (like having been to cinema and the movie was bad or an expensive vacation was not nearly as good as expected or something similar).

For a fatality of a close relative the normal phrase would be

Herzliches Beileid

(Sincere condolences)

If the other person is not - or at least not only - sad about what happened but also (partly) upset (which is possible in all above examples except the fatality), it is perfectly acceptable to not pity that person but rather join that person's anger by saying something like

So ein Ärger!

So ein Mist!

Verdammt!

like you would say damn! or sh*t! in English - or, when someone else is to blame (e.g. in your 3rd example the criticism was unfair)

So ein Mistkerl!

(Such a Son of a B*tch!)

Part I:

I want to know if German speakers, Austrian males especially, feel that by saying "Es tut mir leid" they are expressing guilt and apologizing for a mistake they made.

Yes, the expression es tut mir leid is used by German speakers to apologize for having caused a misery. This is irrespective of the speaker's origin or gender.

Example:


„Du hast den Herd wieder angelassen.“ – „Oh, tut mir leid. Morgen denke ich dran.“

Part II:

DOES IT ALWAYS HAS TO BE LIKE THAT? Or can it also be used to express with empathy that you are sorry about something that is ABSOLUTELY not your fault?

The expression es tut mir leid is also used by German speakers when they did not cause the misery themselves, but when they want to express empathy with the other person.

Example:


„Ich bin heute gestürzt.“ – „Oh, das tut mir leid. Hast du dich verletzt?“

It is also appropriate in all five example situations described in the question.

I'd never use "es tut mir leid" for something I didn't do. Sounds like a bad direct translation from English to me. Only exception would be mean / sarcastic remarks: "Wenn du das nicht kapierst, tut es mir echt leid für dich!"

I can see "das tut mir leid für dich", but it still doesn't sound natural to me.

For expressing emphasis, people could as well try to encourage the person and try to lift their spirits. Depending on the situation you could say:

• "Kopf hoch, nächstes mal klappt es bestimmt." (e.g., after a failed test)




• "Morgen wird's besser" / "Schlaf erst mal drüber. Morgen sieht die Welt ganz anders aus." (e.g., after a bad day)




• "Ist natürlich doof, dass der Chef dich kritisiert hat. Vielleicht kannst du morgen noch mal mit ihm reden, oder sehen, dass du die Sachen, die er kritisiert hat, besser machst." (after the boss criticized someone; this shifts the focus from empathy to helping, and may or may not be right for everyone)