Siegmeyer of Catarina for BINGO
LITERALLY the only square that matters for him, consider it a mini-bingo.
Siegmeyer of Catarina (that is the Dark Souls 1 iteration for those who were about to Google which one it was) always sticks out to me as one of those delicious victims of good intentions. The entire thing about Siegmeyer is that he's a Quixotic figure, a perhaps not too capable golden hearted man looking for adventure and people to save, but that due to his tunnel vision regarding knighthood, ends up tripping all over himself and lands himself in dire situations.
Poor guy just needs a break, and yet, he forbids himself the break until he accomplishes something, anything. One of the few optimistic figures in Dark Souls 1, a particularly bleak entry in the series in hindsight, who ultimately goes Hollow when he realizes... There's not much he can do.
Purpose is the number one driving force in the Dark Souls universe. So long as you have a purpose, you won't go Hollow, because you have something to strive for, something to aim for, something to achieve, and if you can keep picking yourself up, you can keep trying until you get there. In that regard, I think Siegmeyer represents a player that gives up due to not being able to do anything without co-op.
There's no game over screen in Dark Souls. When you die, you are told "You Died" and then you go back to the last Bonfire you used. You died, but you didn't lose. You don't hit the Retry button or the Continue button, no, you are back on your feet and then you do whatever you want. Dying, failing to succeed, is part and parcel of Dark Souls, but it is not losing. There aren't mutually inclusive. There is a way to lose in Dark Souls, however: You lose when you turn your console off, pop the game disk out, and don't keep trying. The world game will never once change again, and you've effectively gone Hollow in a doomed, stagnant world.
The only way to lose in Dark Souls is when you decide you won't try anymore. It's why Siegmeyer keeps failing so much but keeps showing up nonetheless. At the very end, though, when he realizes he can't do anything without your help, that is when he truly loses, and goes Hollow. And it sucks! You were helping him out with good intentions, but sometimes, there's things that one must do by oneself. Maybe you were taught and instructed and helped by someone else, but when someone else does everything for you... It's natural to lose hope, and the drive that pushes you to persevere.
Siegmeyer embodies this aspect of the world in a way I think is very cool.