Out of context, “If I help with anything else, I might end up making things worse. Ya know… cause of my flaws.” is a deeply tragic line.

Not a bad idea for a comment thread. Things you say at the gaming table that, when taken out of context, are horribly sad and depressing. Annnnd... Go!

"I can't tell you the number of times I've lost a loved one when playing a game."

"OK. having to kill my greatgrandfather, i did'nt mind too much... But ended up ruining my relatonships with each of my family members one by one? in the same night?"

(i precise, killing the ancestor was not the cause of any of these conflicts.)

"Did you burn down the city again?"

Maybe not sad, but everyone's still hung up on me asking "How big are your balls?" (Another guy found a hall full of carved demon faces and called back to me to ask what to do. I intended my response as more of a "Do you feel lucky?")

"Friends, You're not my friends?! None of you! I have no friend and will never have!"

"When we die for real, it can only be in the most horrific ways possible."

"Eh, don't worry. I wasn't too attached to this life anyways."

I should know better than trusting you by now. It always ends in a betrayal. And yet i keep making the same mistake.

I don't got a particular quote, but there was the time my magical loli was basically insane for the entire campaign.

Not any particular quotes, but depressed actual magical girl made of cloth is a fun thought.