As the episode begins, a small green person in tattered rags flees from a giant and very angry reptilian beast. The escapee, Woebegone, flees into the ponies' garden and is offered a place to hide by them. When the reptile, an alligatorsaur, arrives, the ponies keep Woebegone hidden and berate it for picking on someone so much smaller than him. The alligatorsaur tells them to hope that Woebegone is indeed not there, and then leaves.
Once the threat is past, Woebegone explains that he's bad luck and carries disaster wherever he goes — the beast was after him in the first place because Woe's luck wrecked his village — and that it's best for everyone if he just leaves. The ponies refuse to hear it, both out of hospitality and because his foot was injured when the alligatorsaur stepped on it, and put him up in the nursery to spend the night. That night, the nursery collapses. As nobody gets hurt, the ponies take Woe and the baby ponies to the main house instead. Woe is cajoled into telling his backstory, and starts to explain how he and friends once antagonized a witch near his hometown when the house's wall falls in.
Things keep up like this for most of the night. Once everyone is asleep, Woebegone decides to sneak out before the ponies are rendered entirely homeless. He stops to tuck one in before he goes. The bed collapses. The ponies notice his absence when repairing their home next morning, and head off to find him — over Lickety-Split's objections — since his foot is still hurt.
They succeed in bringing him back, and his bad luck duly follows. To demonstrate the breadth of the issue to his unbelieving hosts, Woe pats a nearby tree and it promptly collapses. It also releases a river of mud from the hole it leaves in the ground, which sweeps Baby Shady away.
This episode contains examples of:
- Agony of the Feet: Woebegone's foot is injured when the giant alligatorsaur steps on it, and it remains hurt and bandaged for the rest of the episode.
- Bullying a Dragon: The mess Woebegone finds himself in started when he and two other kids decided to have fun by bullying a known witch and antagonizing her for no reason. This endeavor, unsurprisingly, turned out very badly for them.
- Cliffhanger: The episode ends with Baby Shady being swept off in a river of mud and going under.
- Disney Death: Played for laughs when the nursery collapses around the sleeping Woebegone. The ponies have just enough time to wonder if Woebegone is dead before he loudly sneezes.Lickety-Split: He's so still! Is he...?
Woebegone: ACHOO!
Lickety-Split: You're alive! - Heavy Sleeper: The ponies turn to be very heavy sleepers, enough so that neither chunks of the roof falling in nor their bed falling to pieces and dumping them on the floor are enough to rouse them. Woebegone comments on the convenience of this when sneaking out.
- Hurt Foot Hop: Woebegone performs a brief foot-holding dance when the alligatorsaur steps on his foot.
- Toxic Friend Influence: He was goaded into bullying the witch by some friends of his. He didn't really want to, since she'd never done anything to them, but was peer pressured into doing it anyway. Much good it did to him.
- Whateversaurus: Woebegone is introduced fleeing from the latest victim of his misfortune, an alligatorsaur, depicted as a very large, draconic reptile.
