Tear Jerker: Ask That Guy with the Glasses

  • His response to "why does Daddy hit Mommy?" is just a little too close to how Domestic Abusers think.
  • It probably helps if you're a fan of the book, but his quoting of the Happy Place George gives Lenny before he kills him is really well done.
  • Poor GPS. She got proposed to, then had her marriage fail, then when she thought they were going back to being friends, got shot.
  • In episode 50, the narrator sobbing pathetically when Ask That Guy leaves after an argument. Ends up surprisingly heartwarming though.
  • Sitting on a Trauma Swing with the halves of his pipe still in both of his hands. You almost want to give him a hug.
    • Especially if you watch early episodes beforehand where he's all calm and collected, seeing him break so bad under the "true or false" question later is incredibly unsettling.
  • There's something really raw about his self-hating "you're a grown man now!" rant.
    • Speaking of self-loathing, a few episodes later we have this:
    ATG: Yes. Yes, you have. What the fuck is wrong with you?
  • Lampshaded example in the second DVD:
    Narrator: Did I ever tell the story about my friend, Chris? Who got on a treadmill? With a skateboard?
    ATG: [smiling and chinhanding on the bar table] No! Tell me all about it!
    Narrator: Um... I didn't ask the question.
    ATG: [still in same tone] You have three seconds.
    Narrator: Well, I-I don't really know what to say...
    *ATG starts screaming and shooting*
    ATG: Ohh, now I can live a blissful life without the narrator. *immediately eats his gun*
    Caption: It's been decided that this ending is far too depressing to be shown on DVD. We present to you this substitute.
    *ATG then crushes a random puppy first, and afterwards sodomizes it with his pipe.*
    Caption: Fuck it.
  • Episode 62's rampant humiliation. Technically he had it coming, but it's still uncomfortable to watch. Not even Critic had to stoop that low.
  • When he uses reverse psychology on all the hipsters telling them to "not shoot themselves" and they all do so, he declares he loves his job, however, when he's then asked the question "Do you love your job?" He suddenly breaks down in distraught tears showing he feels genuinely guilty that he just made a bunch of people commit suicide and declares he doesn't want to live. Then he goes back to being his calm and collected self saying every once in a while he does have a real human emotion, but he'll always kill it with hatred.
  • When they heard second-hand that Rob said (for the given reason or not) that Ask That Guy was only coming back after a long time gone to finish properly with a “finale arc”, the fangirl tears flooded tumblr.
    • His actual death is very Dropped a Bridge on Him (which is heartbreaking in of itself) and just a way to move the site but he goes back to his old location to do the finale episode and actually has affection for it. It's really sad in a nostalgic way.
    • That nobody really talks about it – Doug even still introducing himself as being known as Ask That Guy in cons – is depressing as well.