I can't reveal mine due to spoilers but one of the guild missions was probably my saddest moment.
Spoiler \The ending of the questline about a certain group people in a certain little mead hall?
If so then same here
If not then the questline about a certain group people in a certain cave outside Falkreath/Dawnstar?
If either of these is what you picked then I thought they were really sad too. If not then I have absolutly no idea what you're talking about and haven't expierenced it yet.
On another account, I found a group of Thalmor escorting a Talos Worshipper, who had his hand's tied, throught the wild. Being a Thalmor hater and beliver of Talos (well my character is, well I personaly hate the Thalmor) I walked straight up the the unrightful prisoner, untied him, gave an axe, snd procceeded to help him beat the mother _______ ____ out of those _______ Talos hating Altmer pieces of ____.
But after the fight I looked for my fellow Talos worshipper and I finally found at the bottom of the waterfall we were fighting next to. I tosssed the Thalmor Justicars down the waterfall and left the axe I gave him, to show that he died fighting for his religious freedom.