Day 9 - Saddest game scene:
This one's super easy for me.
If you've never played FF6 and plan to, spoilers ahead.
At the change to the world of ruin, Celes ends up stranded on an island with Cid. He nurses her back to health, but gets sick. You have to fish to get enough food to keep him alive. If you do a poor job of this, he DIES. And then Celes THROWS HERSELF OFF A CLIFF HOPING IT KILLS HER. When she jumped off I hit reset and tried again and again until Cid didn't die. I didn't, couldn't believe that him dying was the only possible option, for it was too cruel for my twelve year old self to understand. Thankfully you can save him, but this still is the saddest moment in a video game for me.
Click to view
Second place goes to the entire plot of Drakengaard and Drakengaard 2. God DAMN are those depressing games.