What characters journey really bothered you?

Sometimes I’ll read it as a hopeful story and stop the chapter before they get arrested.
If you read it that way it starts as grumpy guy in totalitarian hellscape who hates himself and ends with him having found someone, being enlightened by resistance, and having a will to live.
(Of course the point isn’t to stop there. But sometimes I feel like reading the book again without being too gloomy.)
I think it also helps to understand the context of him writing the book. Specifically his experience as a libertarian socialist in revolutionary Catalonia and the oppression (incl executions and imprisonment) he and his comrades faced from Stalinist factions who treated the anarchists as threats to their power.
- Why 1984 always hit more. Dude was writing from actual lived experience.

At the time, Gollum. Sure he died having retaken the ring but he would have also known that the ring was doomed and above all other things, even his own life, he would have wanted to keep the ring safe. I think it was my first real taste of a character who was completely irredeemable, despite Frodo and eventually Sam offering him kindness and friendship. Was pretty hard ending for a young me to think about that some people cannot be saved.

The Stormlight Archive is all about mental illness so this could literally be any character from that series.

The Realm of the Elderlings series. All books. Most characters.

I'm still addicted to the books though.

I think that's what I must have looked like coming to the kitchen after that scene when I read Winnetou III as a 12 year old.

Robin Swift. I felt equally hopeful and hopeless. Babel sat in my stomach like a painful knot. I haven’t thought about it in awhile but the feeling is still there.

Harry Dresden. His journey has soured me n what for years was my favorite book series.

I requested elaboration
Is this because every time he gets a girlfriend it's only so he can suffer because she immediately dies or suffers a fate worse than death?
- Were any of his girlfriends fridged?

Main character in the Twisted Ones. She left that story as ignorant as she started. I know little about the twisted ones. Why can you get pregnant with a rock? What is the other half, since the children still seem cobbled together? Is it a ritual? What's the source of this power, and what's the purpose of it? Just seems like a bunch of bones and a lady, why go through this? How come Conrad alludes to being extremely old and no one cares or investigates who or what he is? Conrad said he crossed the sea to get to the current location, so how are all these paths connected? Are there portals everywhere? What triggers the shift, or is it one central location? Why was the grandma able to keep them back? What happened to the green book, and if it was so important that Conrad was trying to write it from memory, what was supposed to be in that book? Why did Conrad become one of those things and how does that even work? How do you keep memories when you change forms? WHY DIDN'T SHE BRING ANYTHING TO THE FINAL FIGHT EXPECT THE DAMN DOG!?

It jsut feels like she went to clean up the house, crazy stuff happened, and she just left. Didn't really seemed like she changed or was affected.

Charlie Gordon

Perhaps controversial opinion, but I recently re-read The Little Prince, by Antoine de Saint-Exupéry, and I found the core message to be something of a mixed message. Being responsible for what you domesticate isn't a bad takeaway, but I felt like domestication also extended to friendship and relationships in a problematic way. No spoilers, but it has an ending that can be read as a bittersweet faerie-tale or a deeply troubling message about failure and regret. It meant a lot to me when I read it as a teenager, and now I'm not sure what I think about it, at least not yet.