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- The Sad, Sad Tale of Chickenfoot, where Chickenfoot talks about his past life with Dib where he was a normal man named Chewie Rodriguez until an accident occurred when the microwave was splashed with water while Chewie was wearing the suit and cooking chicken in a microwave, generating an explosion that "created an unholy fusion of man and chicken", causing him go insane and live all alone in an apartment with assorted Chicky Licky toys that he calls his "friends".
- Bad, Bad, Rubber Piggy doubles as both horror and Tear Jerker worthy because of what Zim does to poor Dib by crippling him horribly by tossing rubber pigs into Dib's past through a time machine, replacing seemingly random objects in ways that cause Dib to have horrible accidents, progressively crippling Dib to the point that he almost dies.
- "WHYYYYYYY?!? MY PIGGIE!!! I LOVEDED YOU, PIGGIE!! I LOVEDED YOOOU!!!!"
- Bloaty's Pizza Hog, Gaz yells at Dib for going off to fight Zim because she "just wants to go out to eat with dad." Considering the situation, this certainly counts.Gaz: ...You just don't get it, do you?
- Bloaty. The poor man is completely miserable, forced to do a menial job and gorge himself on pizza.
- Zim's encounter with the adorable blob experiment in "Abducted." He's kept in an isolated room of a spaceship, who hopes someone will rescue him... only to have ZIM nonchalantly leave? The poor creature is left to cry softly...
- "OH, GIR! GIIIIR! THEY'VE TURNED YOU INTO GROUND BEEF! HOW? WHY?????"
- Officer Squidman telling Zim I Have a Family is a lot sadder if taken at face value rather than for the absurdity that it is. Thanks to Zim, he'll never see them again because he doesn't remember them.
- Dib and Gaz's whole family situation. Their dad is so busy, they only go out to eat together ONCE A YEAR. Which seems sort of funny... until you think about it.
- Though Dib seems to care far less than Gaz, interestingly enough. He was more than willing to miss out on that annual family outing without even a hint of regret.
- Dib finding out Dwicky's been lying to him in "Vindicated!" When you see how he joyfully and rather innocently reacts to someone extending a measure of kindness and tolerance towards him, it starts to kind of hit you just how ridiculously YOUNG the poor kid is, and when his "ally" is taken from him it becomes almost impossible not to see just how thankless and lonely a life he lives in trying to save his own people from extinction.Dib: You don't believe me! You... (builds towards rage, then regresses to pleading, and winds up just staring at the ground in defeat) I thought you were different.
Dwicky: Look, I know you think I lied, and I—I did, but I was only trying to help.
Dib (bitter): Isn't this just great?! While you waste my time, Earth gets one step closer to being taken over! That's my problem right there! My problem is that the human race seems to want to be destroyed!
- The hints to Miss Bitters' past, if you think there's any truth to them. Think about it: the creepy Humanoid Abomination that terrifies her students on a daily basis was at some point a normal person with hopes and dreams who got mutated into her current state by a freak accident. Miss Bitters may be a monster, but if these stories are true, can you really blame her?Miss Bitters: I had a valentine once.
- The ending of "Gaz: Taster of Pork". Ok, Dib deserved some punishment for using Gaz as a test rat for his spell drive (good intentions or not), but not only tricking Dib into believing she was in danger when she obviously was not but also forcing him to clean up Shadow-Hog dookie with his head while he's crying for forgiveness? Not to mention all the horrific (and very graphic) death threats and beatings that Dib took from her while he was trying to help her? No wonder Gaz has a bit of a Base-Breaking Character status.
- Well, there was also the horrible experiments that Membrane most likely did to her during her quarantine. It makes it worse knowing that her dad is the only person she has/shows any value for... and since it kind of was Dib's fault and she already has A LOT of disdain for him...
- Dib taking the punishment of the Shadow-Hog to save his sister. He's genuinely crying at the end and feeling guilty...and yet Gaz ignores this completely and leaves him to his fate.
- The intro of "The Frycook What Came from All That Space" marks an especially saddening moment for Dib. After spending possibly minutes to hours attempting to explain to his classmates that Zim is an alien and that they do exist, the kids continuously mock him and cause him to have a momentary mental breakdown in front of the entire class. After cooling down, he tries again only to have a large and imposing alien (alter revealed to be another Irken) kidnap Zim interrupt him while stating it came from outer space. Dib tries to use this as evidence to his statements about aliens only for bird poop to fall on his shoulder from the hole in the roof that the alien created. The kids totally ignore the roof and alien and simply start to laugh at Dib for having been pooped on by a bird. Cue a single tear from a heartbroken and embarrassed Dib.
- Dib's Wonderful Life of Doom. Dib enjoys a life of many achievements in technology and the humanities, and defeats the Irkens in battle forcing them to surrender...until it turns out that it was all a simulation ran by Zim. Why? Because he wanted to know who threw a muffin at him in class. Zim could've just interrogated Dib in a more straightforward manner, but he wanted to twist the knife more by making Dib believe his wildest dreams were coming through before tricking him into admitting it.
- Career Day. Dib gets matched up with Bill, a paranormal investigator; sounds like the match made in heaven, right? Except Bill believes in everything but the existence of aliens, dismissing the Galactic Equinox molt as hogwash. Just to rub salt in the wound, Bill believes Count Cocofang, a cereal box mascot, is real, and chases after the poor man dressed as Cocofang while Dib tries desperately to get him to look at the restaurant where Zim is molting through the doors and windows, without any luck. The molt comes and goes, the only hint of evidence being the completely-destroyed restaurant, and Dib loses his chance to not only expose Zim as an alien but to do so to someone who he thought would be interested in the subject!
- From the brief summary of the plot for Enter the Florpus, Zim despairs over the realization that the Tallests had no intention of coming to the Earth. This could also potentially lead to Zim learning the truth about his "mission."
- The ending of Issue 2 can count, with Dib secluding himself in his room once again in order to hide from ridicule after Zim transmits that embarrassing video to everyone in the galaxy. Dib being wrapped up in his blankets with bloodshot eyes and looking like he's about to break doesn't help.
- Also in this issue, Gir has his legs blown off and is paralyzed, yet Zim and Dib both abandon him.
- Then there's also Zim being trapped on the Gargantis Array after Dib denied him a ride, especially after Zim even referred to Earth specifically as his home. Though to be fair, Zim did have it coming.
- Issue 5. At first, Membrane appears to be keeping up with the streak of being a decent parent to his kids... until it's revealed that he built that alternative world machine for Gaz with complete knowledge that she was going to use it to torture Dib AND participated in the kidnapping sequence.
- Taking a look at this issue from Dib's perspective makes the situation, while still the epitome of Black Comedy, freakin heart wrenching. Yes, Dib should have known by now that not only does Gaz have absolutely zero interest in his hobbies but is, in all accounts, an extremely vicious-minded individual with an extremely short fuse if interrupted. Problem is..even if Dib acknowledges and accepts that he has absolutely no one outside of her or Membrane to turn to given his circumstances. Apparently, he'll risk abandonment, ridicule, and horrific punishment trying to find support from his own family before trucking on completely alone.
- Gaz also makes herself out to be kind of a hypocrite here too. She claims that Dib was selfish for trying to get her involved with his interests, but at the same time not only is she never willing to spare him any time of her own vocation but her obsession with video games is at such a violent level that even Dib's obsession with the paranormal can't compare. And another thing, even when Dib chooses (after the fact) to try and do things that she enjoys, she STILL finds some reason to hurt him (beating Dib up because he happens to win a game fairly). In conclusion, Jhonen was absolutely right about this issue making issue 2 look tame to Dib.
- In Issue 12, Membrane's hologram message laments that the only members of the human race he was able to save were his family...except for "poor insane Dib" because Dib still wanted to fight Zim even if he had to do it alone. Even with that logic, it's obvious Membrane made no attempt to rescue his son for his own good, try to look for Dib if he was captured, or even try to assist Dib at a time where it was obvious Zim was the enemy and winning.
- In Issue 21, when Dib and Zim realize that Gaz tricked them, Dib's reaction is to say, "She played us. My own sister totally played us."
- In Issue 43, Dib is so happy that he's managed to beat Zim for the position of leader of the Plim, and starts talking about how he's going to help them improve their society and place in the galaxy... and then the Irkens show up and take over the planet. Worse, this only happens because Dib took down the anti-technology field surrounding the planet.