Feels Trip

[J.R.S.S.]

To stray from the obvious choices, I'd say the end of Prey.

Spoiler below!

The player spends the entire game trying to save his lover and girlfriend only in the end having to kill her as she was transformed into a horrid thing. At the end of the game, I shook my head with sadness and left my room with a hint of guilt.

And, in a stretch that some would probably disagree with but there are reasons, I would say the entirety of GTA IV leading up to the very end.

Spoiler below!

While the game is full of humor and mindless violence, if one looks at the game as a whole, it's a story of a foreigner trying to achieve the American dream only to be stopped at every corner with death and acts of aggression. He tries and fails, over and over. And then, in the very last act when it seems that he may just achieve his dream, he is forced a decision. A decision that the player doesn't wish to make. Whether his cousin dies (his closet thing he has to family) or his lover (whom he does truly begin to love). One must die, and the player has to pick. Yes, the player can seek revenge on either death but in the end, the realization is there that that character is truly gone.

Then there is the obvious choice of "I Have No Mouth, and I Must Scream" and "To The Moon". Which I need not post any spoilers, for I'm sure everyone here knows already.