Obvious spoilers ahead, duh.

So, which moment in a TES game got you more emmotionally affected? A death of a companion or anything else?

Here are mine:

Oblivion: In the Shivering Isles DLC, Hirrus Clutumnus' quest made me really sad, finding out the reasons he got depressed after we killed him, seems like one of these cases we have nowadays.

Skyrim: When the Dark Brotherhood members got devastated by the Penitus Oculatus.

Nath Dyer, in Oblivion. His letter and the Primroses he is still holding always affect me greatly. I feel so sorry for the poor guy.

Morrowind: The House Hlaalu mission that requires you collect a payment from Llovyn Andus. He has no money but offers to give you his favorite Guar buddy, Corky as payment. He was devastated and it made me feel pretty bad about myself.

Oblivion: There was a suicidal NPC in New Sheoth (Dementia) that wanted you to push him to his death because he was too scared to do it himself. Going to his home, seeing his place, and reading the note he had written was kinda sad.

Skyrim: The orphan kids that Hearthfire added to the game.

Yeah, that's the one I was talking about, complicated name

Giving the poor orphans daggers was pretty sick.

I have to agree with those two

for Skyrim, talking to Balgruuf after taking whiterun for the Stormcloaks.. the whole conversation gave a real "I thought you were my friend, why did you just stab me in the back" feeling..

Poor guy. RIP!

Also a http://www.uesp.net/wiki/Morrowind:A_worn_and_weathered_note from Morrowind I found in an abandoned shack in Gnaar Mok.

The death of Martin Septim (or Joffery and Barurus if they don't make it after the battle of Bruma) is the only thing I can think of.

The only one that jumps to me is a note on the northern shore of Skyrim written by someone waiting to see their beloveds boat pass by, and the sunken ship not far off shore.

Wow, just wow. I feel ashamed to say that this is the first time reading this, a really excellent piece

I copy that one. Drake has grown pretty fond of the heir.

Loosing someone you've sworn an oath to protect with your life, a dear friend even, not being able to do anything but watch, definitely was a hard blow for the little dragon.

Luckily he didn't loose any of the other Blades though. That quickly would've been the end of his self-confidence otherwise.

I remember some sad moments in Morrowind, too, but it's too long since almost to still remember the details.