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.
In the skateboarding sequence, Gumball and Darwin are wearing their usual outfits as opposed to their skater clothes. This is possibly due to it having been produced by a different production team at a different time.
[At the start of the episode, Richard is on the roof in front of his children's bedroom window. He studies the cordless nail gun in his hand before trying to use it on the shingles. Not realizing that it is upside down, he presses the trigger numerous times, unintentionally shooting the nails skyward. A deflated hot-air balloon plummets behind him, its occupant screaming, but he remains unaware of his error. Eventually, Richard peers into what he believes to be the barrel in an attempt to deduce the problem]
[Startled, Richard yelps, firing the gun by accident. The nail lodges itself in the window frame directly above his sons, as they duck for cover]
Gumball: [Leans outside; Angry] What are you doing?!
Richard: I was trying to fix the roof. [Elated] And you saved me.
Gumball: Uh, no, I just saved my skateboard.
[He points at the board, which is partly covering a hole in the roof. Richard drops the nail gun and picks it up instead]
Richard: Oh, is that what this thing is?
Darwin: Yeah, why? What did you use it for?
[During his flashback, he first uses it as a nail file, reducing his fingers to nubs]
Richard: [Gasps; Ponders] Hmm...
[Next, Richard tries it as a chopping block, and the deck hits his face when he cuts on the nose]
Richard: [Slurred] Hmm...
[At the grocery store, he is entirely naked save for his makeshift censor bar. Felicity screams when she sees him, and he starts running]
Hand Security Officer: Stop right there! [Tackles Richard]
[The show returns to the present]
Richard: I've been using it for that thing Gumball said. Land surfing.
Gumball: [Takes the board] Skateboarding, Dad.
Richard: Yeah, but that still doesn't explain why you own a skateboard.
Gumball: Uh, duh! 'Cause I'm a skater!
[A number of nearby townspeople spontaneously burst into laughter]
Gumball: [Insulted] What? Why is everyone laughing.
Darwin: I'm pretty sure Mr. Dad is laughing so he doesn't feel left out. But the others are laughing because you're clearly a poseur. [Steps away from the window]
Gumball: Oh, oh! [Turns to confront Darwin] What do you mean I'm a poseur?
Darwin: Well, I've never seen you ride a skateboard before.
Gumball: Yeah, there's a lot of things you've never seen me do.
Darwin: You mean like how I've never seen you from profile?
Gumball: What do you mean?
Darwin: Well, like how you always hold your head at a three-quarter angle because you look weird otherwise.
Gumball: I don't see how that proves I'm a poseur.
Darwin: So you're saying you're a skater?
Darwin: [Dubious] So you can skate?
Gumball: [Mumbles; Nods] Yes?
Darwin: So if I were to ask you to do a trick right now with this very board, you could?
[Darwin glares at him, and he grows increasingly nervous]
Darwin: [Thrilled] Awesome! Then you can teach me!
[On the roof, Richard is still pretending to laugh, when the nails rain down on his head. Gumball and Darwin exit from the front of the house, the latter garbed in protective gear]
Gumball: [Gasps] What are you wearing?!
Darwin: What's wrong?
Gumball: Dude, you don't wear safety stuff. You just carry it with you at all times, so people know you're choosing not to wear it.
Darwin: But what if I hurt myself bad?
Gumball: Then you get to feature in Elmore Streams' fail compilation of the week.
Darwin: [Fearful] What if I hurt myself really, really bad?
Gumball: Then you get to feature in Elmore Streams' fail compilation of the month.
Gumball: Don't worry, before you can even get on the board, you need to look the part.
Wear And Tear
[Gumball and Darwin head to Elmore Mall and make their way to Skate'R'us]
Gumball: Skaters wear like, rags, and shoelaces for belts, because their identities can't be bought.
Darwin: Where do they get their clothes from, then? The thrift store?
Gumball: No, from the skate shop.
Darwin: What's the difference?
[They enter the store, then immediately come out again with matching outfits]
Gumball: Everything costs ten times as much.
[Soulless Office Worker passes by in the foreground]
Gumball: [Points at him] Ha! You sad conformist drone!
[Several other skaters leave the shop dressed the same as Gumball and Darwin]
Skaters: [Pointing] Ha! You sad conformist drone!
Gumball: That's right.
[The brothers head to another part of the mall]
Gumball: Okay, now we have to figure out whether you ride goofy or regular.
Darwin: [Checks his clothing] I do feel kind of goofy right now.
Gumball: I'm talking about how you stand on the board, dude. Do you lead with your left foot, or with your right foot?
Darwin: I believe all feet were created equal.
Gumball: [Groans] Okay, which foot do you write with?
Gumball: [Sighs] Okay, just let yourself fall forward.
[Darwin complies, face-planting against the floor]
Gumball: What was that?
Darwin: [Picks himself up, injured] I thought that was some kinda skater trust exercise.
Gumball: [Agitated] It was a test to see which foot you would put forward fist, and-- [Face-palms] Okay, do it again.
[He falls on his face a second time, and Gumball sighs]
Darwin: [Muffled] You said "Do it again."
Gumball: Forget it. Come on, let's roll.
[Taking the request literally, he curls into a ball]
Gumball: [Irked] I meant it like, let's split dude.
Darwin: Oh, sorry.
[Darwin stands and, after some straining, manages to bisect his body vertically. Gumball grabs hold of each leg and drags him away]
[Outside, Gumball and Darwin are walking past different shops]
Darwin: So who invented skateboarding?
Gumball: No one really knows the true history. It's origins are clouded in the mystery of many concussions.
Darwin: Dude, it's okay to say "I don't know," or "I'll look it up online later."
Gumball: Of course I know! It all started a long time ago...
[The re-enactment takes place in Victorian Era England. A young boy runs into a blind alley, pursued by some men]
Man: There he is, Lord Hamilton. The ruffian who stole your pocket watch.
Poor Boy: Criminy! I need to find a way to escape from these here gentlemen. Maybe there's something I can use in this alley.
[He spots a plank of wood leaning against the wall, accompanied by four discarded wheels, and the men draw closer]
Man: There's nowhere to run, scallywag!
[His focus switches between the plank and his pursuers]
Poor Boy: Hmm. [Gasps] Hmm. [Gasps] Hmm--
Man: Got ya!
[A shepherd's crook drags him off-screen, where the boy is severely trounced]
Man: Take that! And that!
[Lord Hamilton goes to inspect the aforementioned items]
Lord Hamilton: I say, chaps. I wager one could fashion some sort of vehicle from these.
Man: Capital idea, old boy.
[Later, a number of people are riding around on primitive skateboards]
Man: Good day to you, sir.
Man: Yes, a good day to you.
Woman: Very good day, sir.
Man: Oh, wonderful. Toodle-pip.
[Gumball finishes by humming an excerpt of "Rule, Britannia!"]
Darwin: [British accent] That story sounds like a load of poppycock, m'lad.
Gumball: It doesn't matter, dude. What's important is for you to understand the spirit behind skateboarding.
Darwin: M'kay, what is it?
Gumball: It's a deep and profound philosophy... that mostly centers around ragging on kids on scooters, and people on roller skates.
Darwin: I thought it was about connecting your mind with the street.
Gumball: No, that's what your face is for. But first, we need to get you a board.
All Decked Out
[Now at their destination, the brothers push open the door of Ollie Vendor. It rings a bell overhead, and they step into the center of a dusty, dimly lit room. Around them, the walls are lined with an assortment of skateboards and other paraphernalia]
Ollie Vendor: I've been expecting you.
Gumball: Then why are you not... wearing any pants?
Ollie Vendor: All right, I'm gonna level with you. I was not expecting you. What do you want?
Gumball: For you to wear pants. And a skateboard for my brother.
Ollie Vendor: Hmm... Ah! I think I've just the one. [Pulls a board from a box; Places it on the floor] This one is made of birch and plywood.
[Darwin taps its tail with his foot, causing the deck to flip up and strike his chin]
[The board rolls to the other side of the room and stands on end. A skull adorning the underside comes alive with an evil sounding hiss]
Gumball: Do you have something a little more... flexible?
Ollie Vendor: [Eager] Yes, yes, yes. Of-Of course. [Produces the next board] This one is made of bamboo and the tears of factory workers.
[As soon as Darwin steps on the deck, it breaks in half]
Ollie Vendor: [Collects the pieces] I guess the tears rotted the bamboo. There is... this one.
[When the board is put before Darwin, it appears to glow in the sunlight streaming from a window. A gust of wind rustles his clothing, and he climbs on top. Immediately, he begins to ride around, performing tight circles]
Darwin: Whoa! [Comes to a stop; Whispers] She's the one.
Ollie Vendor: Good choice. It's also a bargain, at only a hundred and ninety-nine d--
[Bringing their business elsewhere, they exit a Dollarama, with Darwin sporting a pink, princess skateboard]
Darwin: Okay, when do we start to skate?
Gumball: Well, first you have to learn the tricks. Here, [Taps his head] then here, [Pats his chest] and, uh, here, [Points to his eyes] then... here. [Points at his teeth]
Darwin: Then here? [Raises his foot]
Gumball: No. Then... here. [Touches his nose]
Darwin: I have to smell the tricks?
Gumball: Uh... yes.
Darwin: You know what I smell right now? Garbage!
Gumball: Oh, well maybe it's, uh, garbage collecting day.
Darwin: [Slyly] That means they'll be collecting you.
Gumball: M-My garbage, you mean.
Darwin: [Wavers] Mm, yeah.
Gumball: [Confused] Wha? Wh-What are we talking about here?
Darwin: I'm saying it looks to me like you don't know how to skate!
[Feigning offense over the accusation, Gumball proceeds to make repetitive gasping sounds while gesturing with his arms in an exaggerated fashion]
Darwin: Hmm. I doubted you for a second, but it's obvious from this over-the-top reaction that you can definitely skate! Come on, teach me some tricks!
[Gumball and Darwin go to a skate park. There, Darwin is watching as his brother silently mouths words]
Darwin: And that's called a... mute air?
Gumball: Yes, and the next trick is called the hospital flip. [Hurls his skateboard straight up]
Darwin: Why is it called a hospital-- [Gets hit by the falling board] Aah! [Bitter] Right.
Gumball: Moving on, the next one is called riding fakie. [Gasps] Look over there!
Darwin: Ah! [Turns around]
Gumball: Oh man, you just missed me riding fakie. That was awesome.
Darwin: Okay, so show me the dark side grind again.
[Gumball rubs his board against the seat of his pants]
Darwin: Uhh, I think I'm ready now. Can we just move on to the part where I actually skate? [Rides away on his skateboard] Come on! Teach me to ollie!
Gumball: Uh-uh I don't think you're ready yet.
Darwin: [Laughs] What do you mean? I'm already doing it.
[His speed increasing, he heads toward the park's exit]
Gumball: [Anxious] Uh, yeah, and you're going a little too fast.
[The path leads him onto a steep downhill street]
Darwin: [Giggles; Realizes his predicament] Oh. Uh, where are the brakes on this vehicle?
Gumball: [Shouting] Dude, jump!
Darwin: [Screams] It's too fast! Save me!
Gumball: I can't!
Darwin: I thought you were an expert in skateboarding!
Gumball: Ah-ah-ah, I said I was an expert in skateboarding, not an expert skateboarder. There's a subtle but important difference.
Darwin: What do you mean?!
Gumball: [Inhales sharply] I'm a poseur, all right?! I never skated because I'm scared of hurting myself, okay?!
[Darwin crosses his arms, scowling at Gumball as he rolls out of view. Gumball starts to run after his brother, then looks at his board and groans. Following a moment's hesitation, he makes the decision to ride]
Darwin: HELP ME!
[Gumball races to rescue Darwin, displaying an impressive amount of proficiency in the process. Up ahead, Darwin is incessantly screaming and panicking while trying not to fall. Coming to a staircase, he barrels down it by sitting on the board]
[Before long, Mr. Small comes alongside him on roller blades]
Mister Small: Come on, jump! I'll catch you.
Darwin: [Eyes his bright yellow and pink outfit] Ew.
[He resumes screaming, and Mr. Small collides with someone on a scooter. Meanwhile, Gumball continues his pursuit by vaulting over Coach Russo's head, after which he dodges between Tina's stomping feet]
Doughnut Sheriff: [Blows a whistle] Stop in the name of the law!
[Gumball leaps through Doughnut Sheriff's mouth hole, and, upon clearing a few more obstacles, catches up to Darwin]
Gumball: [Holds out his arms] Dude, come on!
Darwin: [Shakes his head] Mmh-mnh-mnh-mnh!
[Jumping onto Darwin, Gumball then manages to hop back onto his own skateboard with his brother in tow. Together, they avoid several other hazards, and the street finally levels out, allowing them to catch their breaths]
Gumball: [Chuckles nervously] Did you see that?! Dude, I can skaaa--
[The wheels suddenly strike a rock, launching them both forward. Back at home, Gumball is outside with his skateboard, surrounded by the same townspeople as earlier]
Gumball: Let's see if you're still laughing after this.
[He attempts a trick, but fails, and the crowd walks away laughing]
Gumball: [Does a kickflip] There! Come back! Come back! I'll do it again.
[When he flops a second time, the others leave in laughter once more]
Gumball: [Lands another trick] Aw, come on! If you can only skateboard when people aren't looking, [Picks up the board] then what's the point in skateboard--
[Gumball slams the board onto the sidewalk, and it rebounds directly into his face]