When Poe breaks his leg, he spends his time looking through his telescope. He uses it to spy on his new neighbour and notices that whenever one of his friends goes into the house to visit him, they don't come out. Poe starts to believe that his new neighbour is a psychotic killer and now he must save his friends before it's too late.
Frank and Len are trying to find a singer for the band they're making up for the up-coming "Gloomapalooza" concert, without any success. But then, they find out that Misery has a great singing voice. Problem is, she can only sing good when she's asleep. Meanwhile, Skull Boy interviews Poe, who claimed to be at the very first "Gloomapalooza".
It's club day in Gloomsville and everyone has made up their own club, except for Skull Boy who can't think of a club that really suits him. Then he meets a group of skeletons who love to play jazz and he decides to form a jazz club. But whenever Skull Boy tries to introduce the skeletons to his friends, they disappear and Skull Boy's friends start thinking that he made them up.
A little rabbit appears on Ruby's doorstep and everyone thinks he's so cute. But then, Doom Kitty sees the rabbit stealing stuff from the house. But when she tells the others about it, they think she's just jealous. Now, Doom Kitty must find a way to prove to everyone that the so called "cute little bunny" is nothing more then a dirty, rotten little thief.
The big holiday Yam Ween is upon the gang and things aren't going so well. Ruby has a lot of stuff to prepare for the holiday, while Skull boy tries to show everyone the true meaning of Yam Ween, but nobody will listen to him. Also, when the gang pulls names out of a hat to decide who to give a gift to, Poe's name isn't drawn and he feels a bit left out. (From: http://rubygloom.wikia.com/)
Skull Boy puts on a magical hat that makes him talk like a Shakespearean actor which makes Iris and Misery fall in love with him. In fact, they love Skull Boy so much that they won't stop stalking him. Skull Boy then goes to Ruby and asks her to help him figure out a way to make the other girls leave him alone. But then, Iris and Misery see Skull Boy spending a lot of time with Ruby and they start thinking that she is what Skull Boy likes in a girl and they both start acting like Ruby. (From: http://rubygloom.wikia.com/)
The two Mr. White ghosts are fed up with Boo Boo pulling pranks on people instead of scaring them. So now they try to teach him the right ways of being a ghost. Meanwhile, Ruby tries to help Scaredy Bat overcome his fears and Skull Boy tries to act more civilized after burping rudely in front of Ruby. (From: http://rubygloom.wikia.com/)
Ruby and her friends camp out in the woods in search for the legendary Luna monster, a creature who comes out every blue moon. While they wait, the gang starts telling stories about the Luna and they all start getting scared, especially Ruby who won't admit that she's scared because everyone thinks she's really brave. (From: http://rubygloom.wikia.com/)
Skull Boy and Poe use a time machine to travel back in time to find Skull Boy's ancestors. Instead, they meet Paco, a small budgie who belong to the great poet, Edgar Allen Poe and is a great descendent of Poe. They take Paco back with them to their time and Poe starts to have fun with him. But then, Ruby and Skull Boy find out that if they don't send Paco back to his time, Poe will cease to exist. (From: http://rubygloom.wikia.com/)
Ruby's friends have made it to the finals in a big game show, thanks to Skull Boy, who believes that them winning is because of his good luck charm. But when Skull Boy loses his charm, he loses his confidence as well. Now, Ruby and the others must now try to convince Skull Boy that he doesn't need a good luck charm before the game show starts. (From: http://rubygloom.wikia.com/)
Misery's cousins come to visit to celebrate the 7th anniversery of when Misery was rescused from an ice flow. (The cousins are shown to have caused the first ice flow Misery was in, because during a flashback scene, Misery was waving to the cousins, who were getting buttermilk, for help.) But during their visit, the whole house starts to get really cold until everything freezes up. Misery tells everyone that this always happens when her cousins are together and the only way to stop the cold is to seperate them. Now, the gang is trying their best to keep the cousins separated.
When Misery goes up North to visit her family, Gloomsville gets hit by extremely hot sunlight. The gang realizes that the only way to get rid of the sun is bring Misery back. Now, Ruby, Skull Boy and Iris go through an underground cave that will take them up North and try to find Misery before Gloomsville literally burns up.
Ruby tries to help Iris break a world record, but every record Iris tries is already broken by Ruby. This starts to make Iris jealous and she decides that she doesn't need Ruby's help and goes off to try to break a record on her own. The others fear that this might end their friendship, so they try their best to get Ruby and Iris back together.