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troperville

Entries 20 and 54 can be considered fridge tear jerkers, because they give us glimpses of the person Alex used to be: a friendly, playful young man with a dry sense of humor and a penchant for making bad movies. Then the Operator comes into his life, hijacks his entire personality, and twists him into a murderous madman.
Tim's emotional What the Hell, Hero? rant to Jay, calling him out on Jay's complete lack of anything productive regarding the investigation, and on making Tim's condition worsen by reappearing in Tim's life. Tim's voice audibly cracks several times, especially when he describes how his life has gone to hell over the past three years, due to Slendy's Laser-Guided Amnesia.
- And on top of that, when he leaves, you can just feel Jay saying to himself, "I'm alone." Any help he might have had from anyone, his last thread of hope in finding someone who shares his pain, whose life has been just as ruined as his, who could work with him to discover more or even to end the malign influence on their lives...all gone. In fact, he appears to be wiping away tears.
- And before all that, Jessica confessing to having the same symptoms as Jay. Both the confession itself, with Jessica clearly scared out of her mind, and then her later disappearance. Once again, Jay finally finds someone who could understand, only for them to be ripped away... only this time he shows signs of self blame for getting her involved in the whole debacle in the first place.
Entry #60 reveals that Tim has experienced the health issues that are currently present in him since childhood. (The medical record that was shown was dated to 1995). Just think about that for a second. This sickness he has been shown to have has been going on for the majority of his life. The line he said in Entry #59 makes this hit home even more. "And I start getting better. And I can hold steady work, I can function like a normal human being for once in my life."
- Entry #60.5 delves deeper into Tim's mental health: the problems he's been experiencing since childhood include insomnia, hallucinations, headaches bad enough to cause him to scream, and the inability to experience pleasure or happiness.
  - We have never, in the course of the series, heard Tim laugh with genuine humor, or seen him smile with genuine pleasure.
  - Not entirely true. In Entry #58, Tim does seem genuinely happy to show Jay the abandoned hospital from Entry #56... then Jay insists on going to the one Brian disappeared in and Tim returns to his bitter self.
Some of Jay's tweets really show just how screwed up his life has become.
- On twitter someone outright asks him— "Why don't you bring someone [into the ominous tunnel]?" His answer: "I have no one."
Totheark's "Observation" entry shows Tim in a moment of possibly suicidal despair.
entry/Entry 61 could be considered one. Seeing Tim so frantic, obviously in pain, and even breaking down sobbing before he wanders off as Masky again is heartbreaking. It's almost as if he realizes it's happening again, and knows he's powerless to stop it.
- Look carefully when Hoody opens the box on Tim's bedside table: aside from the empty pill bottle, it also contains a razor blade. And Tim's medical records indicated that he was a suicide risk. Oh, dear....
  - In Entry #65, right as Tim is taking the pills, you can see a scar on his wrist.
- Slightly less despressing theory: some people use razor blades to cut pills in half, such as when their dosage has been adjusted.
  - Unlikely, seeing as Tim's pills are capsules, not tablets. Either he's self-harming, or he has a death wish.
A brief moment in Entry #63: Jay, while waiting in his car, dials a number only to be unable to reach it. The look on his face suggests it's not the first time, and the talk he has with Tim suggests that it's probably Jessica's number. He's been trying to call her all this time in hopes that maybe, just maybe, she'll pick up.
- He also mentions that it's been a year and a half since she's disappeared. Then he forms an alliance with Tim on the condition that he helps him find Jessica. Despite not knowing her that well, he really seems to care about her very much, and he's had to live with her disappearance for so long with little to no clues.
Entry #64: the Operator is coming towards Tim and Jay, while Tim is incapacitated in a coughing fit and Jay is desperately trying to drag him away. Tim can barely speak, but he manages to tell Jay, "Run!"
- Which makes it that much worse when Jay finds Tim waiting in his car...and Tim only gives him a Death Glare before driving off.
  - The desperation in Jay's voice as he shouts after Tim is palpable. Just when he's found an ally, just when he's making some progress, just when he's close to finally getting some answers...it's all snatched away from him. Again.
Entry #65: The first four minutes or so are Tearjerker meets Nightmare Fuel. The rest of the entry is mostly the former.
- Special shoutout to Tim in the burnt-out hospital, sobbing and having apparently reverted to a five-year-old mentality.
- Even moreso when Tim starts to cough and proceeds to swallow his entire bottle of pills in one giant handful.
- Jay's comment of "I'm not really a trusting person anymore, Tim." The tone in his voice is just heartbreaking.
The subtext to Jay's Twitter post about the woman in ToTheArk's videos: he has been poring over them as much as we have, desperate to find anything resembling a hint about Jessica's whereabouts.
Entry #66: Tim blaming himself for the mess that the Operator has caused for everyone. Also, we find out that Brian was his first real friend. They met in college.
- Tim's body language...the hunched shoulders, the near-quivering as he's back in his old hospital room. He's scared and near-broken. That's some truly great acting right there.
Entry #68 We see Hoodie's sparse living conditions, and it's strongly implied that he is a victim of the Operator too. Its a great humanising moment for the character, and is enough to make you feel sorry for the guy.