History TearJerker / RubyGloom

--->'''Iris:''' Ruby, you ok? Cause, if there’s anything wrong, you can tell us.
--->'''Ruby:''' I’m...afraid.
** Frank and Len’s story about the Monster where his ruby went missing and the Monster tore up towns but never found it.
* [[AC:Broken Records]]
Iris keeps failing to break a record while Ruby accidentally breaks records which causes Iris to break up their friendship.
--->'''Iris:''' [[ArmorPiercingResponse I don’t need you Ruby!]]
** Ruby and Iris avoiding each other. Though it turns out Ruby was helping Iris break a record for the longest time lapse between friends.

--->'''Misery:''' What’s that?
--->'''Len:''' Frank’s sweater, he gets cold sometimes on buses. I guess I don’t need to pack that.

--->'''Iris:''' She’s gone, Ruby’s...gone.

[[caption-width-right:350:You know it’s sad when even [[Pollyana Ruby]] [[OOCIsSeriousBusiness can’t even find a bright side to this.]]]]

[[caption-width-right:350:You know it’s sad when even [[PerkyGoth Ruby]] [[OOCIsSeriousBusiness can’t even find a bright side to this.]]]]

[[caption-width-right:350:You know it’s sad when even [[PerkyGoth Ruby]] [[OOCIsSeriousBuisness can’t even find a bright side to this.]]]]

* Doom Kitty being kicked out of the house by the bunny in "Bad Hare Day" and seeing how sad she is while looking at a photo of her and Ruby in the rain.

[[Ac:Science Fair or Foul]]

[[Ac:Science Fair or Foul

* In “Frank and Len Unplugged”, Frank and Len [[FeudEpisode have a falling out]] and they both go solo. When Frank does his solo show, he can’t bring himself to sing until Len joins in.
** Earlier in the episode, Len finds Frank’s sweater.

* [[DisneyDeath Ruby falling off the train]] in “Last Train to Gloomsville”.

* Most of "Hair-Less".

* Scaredy eavesdropping on everyone talking about how his constant drumming was driving them crazy in “The Beat Goes On”.

* In “Broken Records”, Iris keeps failing to break a record while Ruby accidentally breaks records which causes Iris to break up their friendship.

* “Happy Yam Ween”

AC:

* Venus’s reaction to the destruction of Skullboy’s “father” in “Science Fair or Foul.”
** A small one from the same episode, Poe offering to be a father figure and help Skullboy with his science project but Skullboy already built a robot to help.
* In “Iris Springs Eternal”, The gang looking at the hole where she crashes down.

[[foldercontrol]]

[[foldercontrol]]

--->'''Iris:''' She’s gone, Ruby’s...gone.

* If any moment in the series deserves a spot on this list, it's this, even though you won't really get it until you watch more than the first episode. In Gloomer Rumor, even though it can probably be chalked up to EarlyInstallmentWeirdness, that [[EnsembleDarkhorse Misery]], the character who can shrug off things that would '''break''' most people emotionally and most likely physically, openly weeps at the thought of Ruby moving out. The one main character in the entire series who is used to horrible things happening to her and is able to get past them without any trouble, practically breaks down when one of her friends ''might'' be moving out.
* Most of "Hair-Less".
** Skullboy’s solo in the beginning musical number where he doesn’t know where he come from.
** Skull Boy moving out is the one thing that can make Ruby, the quintessential PerkyGoth, forlorn. And not only is Misery also distraught by this, she actually tries to ''cheer up'' Ruby.
** The others also miss him.
** Skullboy being homesick.
* Doom Kitty being kicked out of the house by the bunny in "Bad Hare Day" and seeing how sad she is while looking at a photo of her and Ruby in the rain.

** Everyone besides Ruby blaming themselves for breaking the Yam Ween chime.
** When everyone draws names for the gift exchange, Poe’s name falls through the vent with Doom Kitty being the only one noticing. When Doom and Ruby find it, [[MyGodWhatHaveIDone she regrets not telling anyone.]]
* Skullboy in general doesn’t have any family and sometimes tries finding out where he’s from.

* Venus’s reaction to the destruction of Skullboy’s “father” in “Science Fair or Foul.”
** A small one from the same episode, Poe offering to be a father figure and help Skullboy with his science project but Skullboy already built a robot to help.
* Ruby being so afraid of the Luna Monster that she retreats back to the house while her friends check on her.
--->'''Iris:''' Ruby, you ok? Cause, if there’s anything wrong, you can tell us.
--->'''Ruby:''' I’m...afraid.
** Frank and Len’s story about the Monster where his ruby went missing and the Monster tore up towns but never found it.

** Frank and Len’s story about the Mondster where his ruby went missing and the Monster tore up towns but never found it.

* [[DisneyDeath Ruby falling off the train in “Last Train to Gloomsville”.]]

--->'''Len:''' Frank’s sweater, he gets cold sometimes on buses. I guess I don’t need to pack that.

* In “Frank and Len Unplugged”, Frank and Len [[FeudEpisode have a falling out]] and they both go solo. When Frank does his solo show, he can’t bring himself to sing.

* In “Frank and Len Unplugged”, Frank and Len [[FeudEpisode have a falling out]] and they both go solo. When Frank does his solo show, he can’t bring himself to sing.

* In “Frank and Len Unplugged”, Frank and Len [[FeudEpisode have a falling out]] and they both go solo.

** Frank and Len’s story about the Mondster where his ruby went missing and the Monster tore up towns but never found it.

* Ruby being so afraid of the Luna Monster that she retreats back to the house while her friends check on her.

* Venus’s reaction to the destruction of Skullboy’s “father” in “Science Fair or Foul.”

* “Yam Ween”