Whats the saddest you've gotten during a Pathfinder game (due to the story I mean not because you lost your magic sword or something?) or other rpg for that matter. And have you ever legit cried due to something really sad in game?
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The saddest I personally got was when a particular game, which had amazing intra-party interaction and plot, ended unresolved due to scheduling issues.
I like to play characters with tragic aspects, so when sad things do happen to them, it actually feels satisfying to have that part of their story interacted with and/or resolved.
In a years-long game of Planescape (before Pathfinder was even a thing), I played a goblin bard that sang laments of his dead tribe, exterminated by adventurers. He was joined by the tribe's guardian spirit, a giant ghost raven that watched over him as the last remnant of the clan. Toward the end of the game he found out which adventurers had done the deed, and he began setting up an elaborate revenge scenario in an old opera house. The raven spirit started communicating its concerns to the other PCs, speaking against this vindictiveness over preserving the tribe's legacy. My character went ahead with it despite protests. Appalled by what had been done, the guardian spirit - in effect the last remaining member of his family - abandoned him. I didn't cry myself, but my character sure did, and another player shed a tear too. :V
I was saddened by a player leaving our game.
There was a great amount of RP going on between this character, and the other player's. It lead to be developing Boreal's backstory and personality significantly more than I did originally.
When she left I was certainly not happy with the death of that interaction.
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Recently, my players met a man who was cursed for profaning a temple to Lamashtu; he was immortally stuck in the temple area, and would die only if he left the temple, attempted to reproduce, or was violently killed.
The man's only companion in the long, long time he was stuck there was a qlippoth. The qlippoth wanted to see him die, but not due to anything demon-related.
They wanted to help the man, but when they refused to kill him, the qlippoth turned on them. When the wizard Dismissal'd his only friend back to the depths of the Abyss, he revealed that he was a psychic, whose psychic discipline was emotional trauma. Insanity, Scarring Depression, Black Tentacles, and he went from speaking in a lilting iambic pentameter to nonstop screaming.
The PCs, for their part, didn't want to kill him, feeling sorry for the man. Unfortunately, their first attack crit (dealing more fire damage than they expected), and when they did knock him out, he fell 15' out of the air and into his own Black Tentacles. I ruled that, due to the nature of his curse, upon death, he shattered into a million pieces, and was probably destined for somewhere in the Abyss.
Everyone was deeply saddened, even beyond all the magic emotional scarring he threw at them.
Yeah. It's when the last game session is played, because the players move away, have life issues etc.
A dryad that had been friends with the PCs for a few months (out of game) appeared out of a tree, said the monsters were destroying her sister's trees, and as the group and the dryad were running towards the grove the dryad fell over, dead.