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https://static.tvtropes.org/pmwiki/pub/images/ruby_gloom_skull_boy_and_friends_reuniting.png
It's more than okay
To be part of this fray
From this group I won’t stray
It's called the family.

There's always a Bright Side.

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    General 

  • Ruby Gloom herself has a very optimistic and wholesome attitude, and is really The Heart and Team Mom of her friends. She'd do anything for them, and they'd do anything for her as well.
  • In the show's run it's hard to predict, but it's very hard not to melt when Misery does her characteristic giggle.

    Season 1 
https://static.tvtropes.org/pmwiki/pub/images/ruby_gloom_and_doom_kitty.png
"Will you ever forgive me?"

Grounded in Gloomsville

  • Scaredy saving Ruby from falling off the cliff despite having a fear of flying.
  • Ruby and Scaredy’s relationship in general.
  • The ending sketch that tells how Iris first met Squig.

Doom with a View

  • Doom Kitty jumping into Ruby’s arms.
Missing Buns
  • Skullboy doing Ruby’s laundry since she does nice things to everyone.
Unsung Hero
  • The "Train Wreck" song, written by Frank and Len as a lullaby just for Misery. When they begin playing, Ruby and Iris look confused and even a bit annoyed... then it starts to work. Just the fact that Frank and Len took the time to compose and write a lullaby to help Misery sleep is super charming.

Quadra-gloomia

  • Through repeated head trauma, Frank and Len inexplicably see moments of life through the eyes of Misery, Iris, and Doom Kitty. Then they see Ruby's perspective, and realize she was helping all three of them out, and without seeking acknowledgement. They appreciate how kind she is, and then realize she has an obvious crush on Skull boy. The experiences inspire Frank and Len to write their song about their friends.

Bad Hare Day

  • Ruby apologizing to Doom and them making up at the end.

Happy Yam Ween

  • Most of the episode, where the true meaning of the holiday is friendship, and they all decide to have fun in the end.

Once in a Blue Luna

  • Ruby becomes scared of the Luna Monster and later hides inside the house so the others go to comfort her.

Time Flies

  • Poe’s relationship with his ancestor Paco.

Misery Loves Company

  • When Misery is stuck on an ice flow...again. She does only one think to help cheer herself up. She sings a certain lullaby written by two of her friends.
    Misery: "~Is your ship sinking? ~Did you know that's arsenic you're drinking?..."
  • Malady and Malaise willingly separate so that the Ice Age they cause when they're together doesn't ruin Misery's anniversary party.
  • This exchange:
    Ruby: Let's really get this party started, Misery. Things are no fun without you.
    Misery: Gee. That's the nicest thing anyone's ever said to me.
  • Despite the fact that their mere existence is capable of causing an ice age, Misery clearly loves and cares about her cousins. She admits to Ruby that the surprise of the two of them was a nice one, and makes her rare Signature Laugh.

Sunny Daze

  • Misery leaves to visit her family while the area becomes so hot, everyone hides in her room until she returns and they all welcome her back with a hug.
  • Ruby almost confessing her love for Skullboy until Iris interrupted.

Broken Records

  • Iris saves Ruby from falling down a well, sacrificing her chance at making a Gloomsville record. Also them making up right after.

    Season 2 
https://static.tvtropes.org/pmwiki/pub/images/99190e0b_28e9_46f3_8c84_d499ee64b4f0.jpeg
"Skullboy, it’s you!"

Gloomates

Tooth or Dare

  • Scaredy’s friendship with Milli.

Hairless the Musical

  • Look on The Bright Side.
    • And it’s sung again when Skullboy cheers up Ruby when he reveals he’s leaving.
  • Even though it’s also Tearjerker, "Bummed Out" where Ruby and the other miss Skullboy.
  • When Ruby starts to feel down, Misery of all people tries to cheer her up. Ruby admits to her that being "The Happiest Girl" isn't always easy, so Misery offers to try taking over the role (and quickly fails). Ruby then tells her not to worry, and their ensuing duet "Dark & Dawn" is basically them reassuring each other that they're content with who they are.
  • Skull Boy realizing he misses Ruby and his friends, and choosing them over a life of fame.
  • Skull Boy realizing Ruby and his friends are his family.
  • Skull Boy and Ruby’s reunion, everyone reuniting with Skullboy, and the accompanying song:
    It's more than okay/To be part of this fray/From this group I won’t stray/It's called the family
    • The fact that the Whites were the ones to finally convince him about staying with his friends.
    • Who does Skullboy hear right before the reunion? Ruby.
    • Everyone’s huge smiles. They practically wished he would come back which was something they all thought would never happen. So seeing him again after so long is refreshing.
    • Scaredy is flying to Skullboy instead of running like he usually does.
The Beat Goes On
  • When Scaredy goes missing, Frank and Len consider canceling the show because it wouldn’t be the same without him.
Forget Me Not
  • The gang trying to get Skullboy’s memories back.

Frank and Len Unplugged

  • Before Frank’s show, Frank and Len tell Ruby to tell the other one some advice.
    Len: Ruby, can you tell Frank to have a good show? And-and tell him even though I can’t be up there with him. I’ll be there in spirit.
    Frank: Ruby, Can you tell Len…(To Len) Thanks buddy.

  • Frank and Len making up.

Disaster Becomes You

  • Very brief, but Misery’s happiness at remembering the one male member of her family that wasn’t killed by quicksand.

Last Train To Gloomsville

  • Ruby and Skull Boy exchange the longest hug between them in the series. They get really nervous about it afterwards too.


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