The episode starts with Richard fixing the roof and almost gets himself injured. Gumball and Darwin interrupt him at the right time to stop him from using Gumball's skateboard to fix the roof. Darwin then asks what Richard was doing with the skateboard in which Richard has brief flashbacks of him misusing the skateboard. Richard tries to cover up his misuse by claiming he was using it to "land surf" and questions why Gumball has a skateboard. Annoyed, Gumball declares that he's a skateboarder and the neighborhood begins laughing at his unproven claim. Darwin points out that Gumball hasn't shown to do any skateboarding in the past, causing Gumball to lie about being a professional skateboarder. While skeptical at first, Darwin eagerly asks Gumball to teach him how to skate.
In the next scene, Gumball and Darwin leave to practice how to skate. Gumball questions Darwin's choice to wear safety gear and Darwin explains that he doesn't want to get injured. Much to Darwin's dismay, Gumball tells him that safety gear isn't a good choice to wear and takes him to Skate Shop to "look the part". Afterwards, Darwin asks about the origins of skateboarding and Gumball makes up a story about a poor boy robbing Lord Hamilton and ending up getting captured. In this story, Lord Hamilton discovers a wooden plank near some wheels and gets an idea to create vehicles which would later be known as skateboards. Darwin doesn't believe the story to which Gumball writes off as they go to buy a skateboard.
Gumball and Darwin come across Ollie Vendor, who tries to sell them some skateboards. The first one attacks Darwin, the second one shatters as soon as Darwin steps on it, and the third one is too expensive to purchase. They leave to go to the store to by a cheaper and stable skateboard so that Gumball can teach Darwin how to skate. Gumball tries to make up some tricks but then Darwin believes that Gumball doesn't know how to skate. After Gumball gives a egotistical and over the top response, Darwin takes back his doubt and they continue with Gumball teaching Darwin.
Gumball makes up some more tricks about skateboarding, prompting Darwin to move onto skating by himself. Unfortunately, Darwin ends up skating too fast causing Gumball to admit that he lied about being a professional skater and that he never actually skated before. Gumball then attempts to skate in order to save the now agitated Darwin. This leads to an sequence of Gumball efficiently skating and eventually catching up to Darwin. The scene ends with the skateboard hitting a pebble, causing Gumball and Darwin to trip over it.
Afterwards, Gumball attempts to impress the neighborhood with his new abilities to skate but ends up failing. An irritated Gumball questions what's the point of skating if he can't show it to other people and accidentally hits himself in the face with his skateboard, ending the episode.
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[Episode begins with Richard on the roof with something in his hand; he fixes the roof, but a lot of screws come out, revealing the tool's the wrong way; a man on a hot air balloon screams; he thinks for a second, shakes the tool, and sees what's inside; the camera zooms out, revealing Gumball and Darwin]
Richard: [Screams and accidentally aims at the window; Gumball and Darwin crouch]