Skyrim is a game with a thousand stories. Actually, it’s probably way more than that. We didn’t count all of them. But every player soon finds out that is a massive land with a story around every corner, often too many to even try in one playthrough (especially if you don’t like quest markers on your screen).

Most of these quests are the tame fantasy tropes we know and love. Go find the lost sword, go find the enchanted ghost, go find the other lost sword, go find this mace, it’s slightly different from a sword. You know the drill. But Skyrim goes way beyond these normal quests and serves up all sorts of other stories. Some are amazing, others are rewarding, and quite a few are…too much. They cross a bitter line, either when it comes to morals (even if you are playing a bad guy) or when it comes to how the player feels.

This time, we want to celebrate those “too much” moments, the times in Skyrim when you say “Yikes,” and very often, “I’m not sure I wanted to do that.” We all know the feeling, and in Skyrim, you get to feel it, well, quite a lot. So here are the nasty moments, the controller-breaking moments, the times where Skyrim crossed a line and you needed to take a break, physical or emotionally. Sometimes it’s an assassin mission, sometimes it’s a side quest that really didn’t go as planned, and sometimes it’s a horrible, soul-wrecking choice that you just had to make.

25 The Sacrifice Of Boethiah

Boethiah is a Daedric Prince, so you know she/he wants you to do some ugly stuff straight away. Well, Boethiah sort of specializes in making you do extra borderline stuff. For example, her first task is giving you a dagger and saying, “Hey sacrifice one of your good friends on this magic altar.” Because you are a heartless fiend, you immediately go find a friend and lead them to the altar, where they get strapped in and you use the dagger as you know best. Boethiah then possesses the body and gives you the next task, which also isn’t great. It’s a worrying thing when you have to decide just which of your followers around the world is expendable enough for this ritual, and all you get is some…really amazing armor. Oh. Okay. Time to go find Faendal, we guess. No one misses him.

24 The Final Deal of Hermaeus Mora

Mora is the Prince of hidden knowledge and other tentacly things, so it’s no surprising he wants you to do some creepy things. In Dragonborn, he asks you for the knowledge of the Skaal, which is hidden in the mind of their wise man, Storn. If you want to complete the story, you have no real choice but to offer Storn up to Mora as a sacrifice. Unfortunately, this progress as gross as you may imagine:

Mora rips out his mind with an attack of evil tentacles and leaves him an empty vessel on the ground.

The sadness lasts for about two seconds, until you are ready to go confront your nemesis and end the story. Poor Storn’s fate is almost entirely ignored, except for the nightmares you may experience at a later time.

23 Betraying Rieklins And Just…Everyone

There’s a place in Dragonborn called Thirsk Hall, and if you find it, you discover that it has been taken over by Rieklings, little imps who usually fight you but this time, ask you for some help in getting the Hall back in shape. At first, the quests are cute and innocent, but then they take a darker turn when the Rieklings ask you to destroy the human band that used to occupy the Hall.

You have a choice to help the humans or the Rieklings, but either way, it ends poorly.

You have to wipe out one of them, and in the end, you fight the Rieklings to be chief anyway, so it all ends in slaughter. There’s not much reward, so you sort of feel bad starting the quest in the first place when there’s no happy ending.

22 Telling The Old Alchemist About Her Daughter’s Fate

This one is a short quest but it hits so hard you don’t really want it to exist. In Solitude, there is an old woman alchemist who asks you to find out about the fate of her daughter, a soldier in the civil war. If you agree, you can go ask a captain about her, and find out that she recently perished in a battle.

There is no reward for this quest. It is nothing more than a gut punch right in the feels, and leaves everyone feeling bad.

Then go back to the alchemist and tell her the news. She totally collapses at the news, and tells you that she cannot thank you for the news, but understands what you have done. This quest totally crosses the line.

21 Unavoidable Fates For The College Of Winterhold’s Professors

One of the worst things in a video game is when characters you know fall in battle without you even knowing – and without you being able to do anything about it. This exact thing happens toward the end of the College of Winterhold quest line, when you finally go to confront the evil Ancano in the College center. Here you find that the Archmage of the College, Savos Aren, has literally died off-screen.

It’s a cheap way to speed up the end of the story and annoying because there’s nothing you can do.

In fact, all the professors have been fighting off the screen while you were busy passing out and generally just being useless.  After all, at this point, you may well be more powerful than all the professors combined.

20 A Deaf Woman In Her Cellar

During the main storyline, you eventually wind up in the endless cells under Riften. It’s a fun little mission to find an old scholar locked in his prison, but it gets way too tragic when you find Hefid the Deaf, who is in her own little cell hidden away from everything. She endlessly goes on about all the objects near her, muttering, “Inkpot, stone, bucket,” and so on, never stopping. There’s nothing you can do to help her, and trying to interfere in any way doesn’t make a difference. She’s just a lost crazy woman in an old cell, and we really think that’s pushing the limit. It ignores all the good rules of gameplay. After all, you don’t even get a quest from her.

19 The Victims In Windhelm

There’s a famous quest in Windhelm that triggers when you visit a few times. A serial attacker is on the loose in the snowy streets, and you have to solve the mystery of who it is. To avoid spoilers, let’s just say it’s a madman who wants young female bodies to cut apart and so that he can reconstruct the body of his lost love.

You find evidence of his secret experiments in detailed journals around the city, and a hidden room with an altar filled with grisly remnants.

You expect a lot in an Elder Scrolls game, but such a creepy serial slaughterer still managed to catch most players off guard. It feels particularly good if you managed to stop his last crime, but at the same time….gross.

18 Completing The Dark Brotherhood

Okay, we talked about eliminating the famous chef, but this one goes way beyond that, and it’s very spoileryfor the Dark Brotherhood questline. Ultimately, you decide to eliminate the emperor of Cyrodil (after being cheated out of it the first time). The big problem is that he’s actually a really good emperor. He’s an old man doing the best he can in a tough situation, and you’re just an assassin who’s getting some sort of cosmic revenge on the world.

When you finally confront him, he calmly explains the situation and lets you know that he has accepted his fate…

Generally just making you feel like a little child as he sits at his desk and waits for the end. It’s not your best performance, but by this time most players probably go through with it.

17 The Vampire Boss Immunity

The Dawnguard expansion gets a lot of things right, including extra powerful vampires, surprisingly cool vampire hunters, and a ton of crossbows, which automatically improve any game. But let’s fast forward to the end of the DLC, where you fight an ancient vampire with a magical sunbow. Classic, right? But the fight itself is incredibly annoying for players: The vampire himself zips around the room in a cloud of bats, making him really hard to hit, especially for melee characters. But he regularly goes back to his fountain of blood and becomes immune to all attacks, which is an absolute no-no. To prevent him from recovering health, you have to pull out the magic bow, equip the special arrows, and then manage to hit him. If you aren’t an archer, it’s pretty much the worst thing ever.

16 Giving You A Room Filled With Gold…And Madness

Let’s talk about a different line to cross: Giving you carpal tunnel. This particular quest happens in the Dragonborn DLC, which is all around excellent and includes a ton of quests, some of which are pretty hard. One of them has you search for pieces of a map to find a buried pirates treasure and powerful cutlasses, because sometimes Skyrim is extra awesome. But here’s the thing:

You finally find the secret cave filled with loot, and it’s very literally filled with loot.

There are dozens and dozens of golden coil piles lying everywhere, and you have to pick every single one up at a time. It takes forever, but each pile is worth just enough to make it worth it, and slowly drive you crazy.

15 The Necromancer And His Mad Ghosts

Out of so many messy quests, this particular quest is notorious for being one of the most creepy. It’s about a necromancer who settles in a barrow beside a town and starts experimenting. There’s no easy way to say this…he starts taking some of the zombies as lovers. When that isn’t enough, he captures a local girl and turns her into a ghost so he can get another warm embrace…and then he starts doing it again and again. When you find him at last, there’s a ghost in his bed and you feel no remorse whatsoever about ending the entire thing. It’s a good thing you can shout people into walls over and over again, isn’t it? Oh, and make sure you recover those journals of his, because people will, uh, pay for them.

14 Helping Neloth With His Experiments

Good old Neloth! He’s a crazy Telvanni wizard living in a giant mushroom, as they do. You can help him with all sorts of mad experiments, but that’s normal so we’re going to skip by that and head over to the main quest he gives you once he trusts you enough. It’s a seriously messed up story about how he took his old steward and ripped out her heart to replace with a magic volcano stone…just to see what would happen.

What happened was that she became an undying lich of vengeance and started summoning ash spawn to attack her old master.

You have to take care of the problem by heading to her castle and, well, ripping out her heart again, except this time it’s the stone one. At a certain point, maybe there’s just a little too much heart ripping going on?

13 Helping The Crazy Argonian

Well, there are a lot of crazy Argonians in Skyrim, which is sad but understandable, because they are lizard people living in a freezing cold northern land. One of the craziest is in Riften on the docks, called From-Deepest-Fathoms. When you speak with her, she babbles about hearing voices and generally being super insane – and then she asks you to take a magical cube to an ancient dwarven fortress. You want to help her out, of course, so you agree.

Then you find out she was part of a band of thieves trying to steal the secrets behind the ancient fortress.

Due to the traps, she was the only one who survived, and the knowledge she stole drove her crazy. It’s pretty dire, but you do get a sweet permanent bonus out of it.

12 Sheogorath’s All Too Real Insanity

Sheogorath is the Prince of Madness, so his quests usually involve some strange things. But Skyrim’s version is unusually dark and hard-hitting. You go into the mind of Pelagius the Mad, an ancient emperor who was, well, mad. Sheogorath is reigning there with a dinner party and several quests for you to do. But the quests are particularly horrible, because each involves a factor that makes Pelagius crazy. In one, he is a child haunted by nightmares you have to fight. In another, you have to intervene in an endless duel that represents paranoia. It’s all weird and a little too private, and you wonder what good it will do, because this guy died a long time ago. At least you help him out, but the creepy journey is what sticks in your mind. That, and the strange dinner party.

11 Striking Down The Only Good Dragon

Skyrim is about destroying dragons. Duh. But there’s one exception. That is the ancient dragon is Paarthurnax, and he is the sort of master over the Greybeards, teaching them how to shout. When you finally meet him, he talks about how wrong the dragons were, and how he has spent thousands of years trying to make amends (oh, and he trains you too, so you get extra powers). Then you join the Blades, because the story makes you, and they order you to destroy him.

The super sad part is that if you go through with it, Paarthurnax agrees and says he will fight you in a noble duel as his final sacrifice.

Well, there are the feels, right on time. Many players actually stop the Blades quest right there because they refuse to do it.

10 Making Forbidden Legend Too Hard

Forbidden Legend is easily one of the best quests in Skyrim. You find an old book and complete several quests to seek out long-dead brothers who were all incredibly powerful wizards. One of the first brothers is part of the College of Winterhold story, and he’s a pushover, which may give you the wrong idea. You see, the problem is that another of the brother is a magical teleporting ghost with the Unrelenting Force shout.

Most character builds have a huge problem with this — because being incapacitated throughout a boss fight is no way to build a game.

When you fight him, he has a habit of disabling you for long seconds at a time by shouting you into a corner and ending you with attacks, no matter how powerful you are. In the final stage of the quest, he does the same thing all over again, but much harder.

9 Everything About The Soul Cairn

Gamers like to know where they are going. It’s the general rule, that you don’t confuse people too much. But the Soul Cairn crosses the line and then goes to the bathroom on it, because this place breaks all the rules. There’s no clear map, everything looks the same, and you can follow vague glowing towers for hours before you realize you are going in circles. It doesn’t help that there are a bunch of quests and unique spells in the area, because that actually gives you a reason to not have fun. This place makes you feel horrible, and that’s just not cool, Bethesda. The only good thing we can say is at least this place lives up to its name and story, because you really do feel like a lost soul by the time you are done with it.

8 Cursing You With Annoying Zombies

When a game gives you an ability, it shouldn’t drive you crazy at the same time. Unfortunately, the raise enemy skill does just that, as all necromancers have quickly found it. Normal enemies, when resurrected, follow you around and endless go “mmmmmmehhhhhh,” especially when you think you are in a dark corridor all alone. Named enemies are even worse, because when you raise them they repeat their few lines over and over and over again. It quickly makes the skill worse than anything in the game, especially when you find they don’t so much attack your foes as much as they just stumble around moaning. Nope, it’s too much. We will just summon atronachs from now on, thank you very much.

7 Dealing With The Greatest Chef

There is a famous chef in Skyrim, and if you seek out all the dialogue options you can find multiple people murmuring about how exciting this is. You can even find his servant out in the wilderness, hunting for rare ingredients. It’s a fun little side story, until you join the Dark Brotherhood and carry out their various exterminations: One of the most important in the final quests is hunting down the chef, known as The Gourmet, and eliminating him so that you can take his place.

There’s even a bonus if you hide his body in a nearby lake and make it look like an accident.

It’s one of the darkest quests because he’s just a famous chef who brings yummy joy to people everywhere, and you only see him as a means to an end. Hey, assassins, what did you expect?

6 Betraying Your Friends To Power A Sword

The Daedric Prince Mephala has been known for making you do creepy stuff, long years before Skyrim ever came out. But her quest in this game really crosses a line: Here, you can find a partly-possessed child of a Jarl who has been listened to a secret voice from behind a locked door. Sure, it drives the kid insane and that’s not cool, but the worst happens when you open the door and find a powerful Daedric sword with amazing life leech…and a hideous catch.

To fully power up the sword, you have to hunt down people you have befriended and who will follow you, and sacrifice them to the blade.

You have to really, really want this sword to complete the quest, and it’s pretty clear what sort of person you are by the end.