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  • Alternative Character Interpretation:
    • It's never really explained which websites on the Deep Web are truth and which ones are lies, and to what extent.
    • Why does the player character never call the cops? Is it because it seems too outlandish for the police to believe, they enjoy the danger, or Lydia doesn't want to get caught by the cops as a sexual predator?
  • Complacent Gaming Syndrome: It's generally agreed that the best way to start each playthrough is to complete both the ChosenAwake and Claffis puzzles first to unlock the second and third deep web wiki pages. The Kidnapper and the Breather don't become active until you have found your first code, at which point it becomes much harder to concentrate on doing the puzzles (especially Claffis), so it's beneficial to get them out of the way early.
  • Complete Monster:
    • First game & The Waiting Room DLC: The Executioner is the sole runner of the Red Room, who kidnaps and tortures innocent people for the entertainment of The Deep Web watchers, with his dungeon filled with medical and acid equipment as well as tapes of his crimes. Taunting his victims and laughing at their suffering while acting as an entertainer to the sick livestream watchers, the Executioner shows himself to be one of the most depraved people on the Deep Web.
    • First & second games: The Doll Maker is a surgeon hosting a website on the Deep Web to sell his products. Buying poor women from halfway houses, the Doll Maker takes them to his clinic and transforms them into "easily manageable toys", amputating their arms and legs in the process. After the transformation, the Doll Maker psychologically tortures them until they accept their new lives, keeping two "living dolls" for himself. The women who suffered this fate are completely aware of what is happening to them, but are unable to move or speak. In the sequel, the Doll Maker "improved" his methods so his victims would last longer and be more obedient. Tracking Clint Edwards after he visits his website, the Doll Maker leaves a living doll with signs of abuse in front of his door and shuts off his energy, then puts a knife against this throat and politely tells him that he hopes Clint enjoyed what he had seen, before threatening to kill him if he doesn't give him a woman from his own apartment complex to be his next victim.
  • Crosses the Line Twice: Despite the nightmarishly twisted tone of the game, some things you find will cross the line from horrifically twisted to hilariously absurd, such as someone confessing to wanting to pee on everything valuable somebody owns and an obvious pedophile being killed on the spot after the hackers get a request from him.
  • Creepy Awesome: The Breather. A creepy masked Serial Killer who breathes loudly and will kill you if he gets the chance. Despite this, he has a hefty fanbase thanks to a cool design and concept.
  • Ensemble Dark Horse:
    • The Breather was so infamous he got to return in the sequel. It may have something to do with him being creepy and cool.
    • In a very dark way, The Dollmaker is this. He is not liked, per se, as much as he is well-received for being absolutely terrifying. In many ways, he is the face of WTTG.
  • Evil Is Cool: The Breather has a rather cool design and his absolute Nightmare Fuel has made him an Ensemble Dark Horse.
  • Fridge Logic: The idea that you can be kidnapped at any time just for browsing the Deep Web implies that there are potential kidnappers literally everywhere just waiting to pick up a Naïve Newcomer, which is either a major dose of Paranoia Fuel... or a giant break of one's Willing Suspension of Disbelief.
  • Funny Moments:
    • Despite the game's dark tone, there's a moment of Black Comedy on the "Black Hat Post" website. The website's premise is that, for a price, hackers can find out information like addresses, passwords, and so on. One person asks them to identify a woman in a picture, seen from the back. Their response?
      "Idiot, you need a picture of the face. Thanks for the free money though."
    • From the same website, some person asks the hackers what is the password of YouTube Let's Player CoryxKenshin. Apparently, it's 'DatBootyDoe7'.
    • "Nude Youtubers" is a canon website in the game you can get into, Good Lordy. They're literally just nude model images with youtuber faces superimposed onto them.
  • Good Bad Bugs: One of the things that makes the game so difficult is that the Kidnapper can attack you while dealing with the Breather and vice versa. When you're holding the door shut to keep the Breather out, the Kidnapper can sneak into your home and catch you on the way back. However, if you look through the door window and turn around to click the doorway to return to your desk at a precise time (specifically just as you reach the highest point in the peeking animation), the Player Character will moonwalk there instead of walking normally. This prevents the Kidnapper's doorway Jumpscare from occuring and may give you just enough time to hide.
  • Narm:
    • The torturer in the Red Room livestream is going for a Mark Hamill Joker impression, which can take away some of the scare factor for some players.
    • Similarly, in the secret ending where you play as the victim, the torturer catching up to you in the end is pretty scary at first, until you realize that he somehow just teleports in front of you onscreen. Must be a really fast guy.
    • In the Waiting Room, one of the Executioner's jumpscares is to punch you in the face. Scary to some, slow and goofy to others.
  • Paranoia Fuel:
    • Much like the creator's previous game Rides With Strangers, the game heavily goes for a very grounded and somewhat believable form of horror, Fridge Logic aside. You spend the game in a quiet and empty house surfing disturbing websites ranging from black markets selling creepy illegal stuff to serial killer confessions, while a strange kidnapper and a serial killer are scouering outside your home trying to get in. Then you hear a chair scrape across the floor while you aren't looking...
    • Though a minor example considering everything else in this game, the fact that you constantly getting hacked by unknown people can be quite tense, especially when it distracts you from someone who may be trying to get into your house.
    • The fact that the deep web actually exists, and some people use it to stalk others. You're not safe from the horrors of the deep web.
    • The hacker blog zeroDay is full of this. Some of the posts describe how easy it is to hack into mobile phones, and how stupid people are for leaving valuable information such as passwords on there. And how people use only one e-mail for every account, and other mistakes people make that makes them easier to hack... It'll definitely make you question just how safe your information really is.
  • Player Punch: If the player doesn't know what a Red Room is, it might give them a nasty surprise at the end.
  • Scrappy Mechanic:
    • The hacking minigame where you type lines of code is less than well-received, to say the least. The issue comes primarily from how little time you are given to complete all of the lines, often requiring you to be both extremely fast and not make any mistakes to stand any chance. To some extent, the constant hacking in itself can be quite annoying, primarily by how frequently it occurs.
    • The whole kidnapping/killing subplot puts a huge damper on what would otherwise be a morbidly fascinating web crawl. Thankfully, version 2.0 added Casual Mode, allowing you to browse at your leisure.
  • That One Puzzle: In order to find the Red Room and complete the game you need to find eight codes hidden throughout the deep web. There are two wiki pages in addition to the one you start with, each of which needs to be unlocked by completing the puzzle on ChosenAwake and Claffis respectively, and you need all three wikis to access all codes. ChosenAwake isn't too much of a hassle, since it is just asks you to click a set of symbols that doesn't change between attempts. Claffis on the other hand can be very frustrating. This page has the appearance of a music sheet and will play a series of notes when you interact with it. You need to pay attention to each note being played and click on the correct ones in the order they were played. Unlike ChosenAwake, this sequence does change if you get it wrong, so better hope you have a good memory or you'll need to write the sequence down somewhere.

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