Jillian Beanstalk gives Humphrey Dumpty a crash course in bravery, but will he rise to the challenge and face his fears or crack under the pressure?
A crowd of students inquire on campus to watch Jillian Beanstalk, daughter of Jack from Jack and the Beanstalk, climbing to the top of a very large beanstalk. As Jillian is done excelling, she is then seen carrying a Goose that Laid the Golden Eggs, and a female harp. After parachuting down, everyone was so impressed, even Coach Gingerbreadman claimed she broke a new record. Later, she goes over to Humphrey Dumpty, son of Humpty Dumpty, asking him if he is okay - which then he exclaims that she has to teach him how to brave. After being bribed by some (regular) beans, Jillian agrees to help the boy.
However, through every height in the school Humphrey failed (to hilarious results) and Jillian's annoyance. Outside the high tower of Ever After High, Humphrey faints due to the high height; being shown a lower balcony causes Humphrey to scream and run away. Even he couldn't climb on the very branch of the beanstalk, which he explains he's too scared. Nevertheless Jillian gives the boy encouragement and advice even though she nonchalantly gave up teaching. While Jillian is in a classroom writing, she overhears Daring Charming ask aloud if Humphrey Dumpty is climbing the Beanstalk. Then the scene flashes to Humphrey climbing the stalk when the Stalk is about to break. Opposite him is Jillian, jumping over to Humphrey's side, holding out a hand and a long branch to help, but Humphrey lost his confidence to move.
Jillian quickly pretends being in trouble so Humphrey courageously swings over, saving her. Next, she falls down with Humphrey, hand-in-hand, before pulling her parachute. They both fall down, the crowd cheering both her name and Humphrey's name. Humphrey soon falls off the wall, but he gives them a thumbs-up and they restart the cheering.
- When Jillian Beanstalk's name intro flashes up, it says her parental information, that she is the daughter of Jack Beanstalk, not just daughter of Jack, like Alistair Wonderland was only alone called "Son of Alice" on his doll box.
- This webisode shows Humphrey has acrophobia, or fear of heights.
- Meeshell Mermaid makes her webisode debut.
- Jillian makes her webisode introduction, but not webisode debut. Her webisode debut was in "Piping Hot Beats".