The plot is about King Dedede and Tuff suffering from toothaches and having to see Dr. Yabui about getting their cavities filled, despite both of them being very squeamish about it. Dedede eventually orders a Monster (Hardy) to do the job anyway as usual since he doesn't want to see Yabui, but he is just as scared about it, if not more. Hardy treats everyone, and puts a drill near Tuff's cavity, but doesn't drill the tooth. It just scares off the things that caused the cavity. Dedede wanted his cavity fixed another way, so Dedede fled from Hardy. Hardy went crazy when he realized that Kirby has no teeth, and ends up being blown away, so Dedede ends up at Yabui's screaming his lungs out when he gets the treatment the hard way.
Spoiler alert: The following section contains plot-specific details.(Skip Section)
The episode starts with Chief Bookem having his cavities drilled, but he doesn't want to have them drilled. Escargoon has a toothache as well. Kirby puts his hand by his mouth and it makes him look like he has Toothache. Escargoon is having his tooth drilled. Then, Yabui starts to pull them out with a pair of giant pliers, but Dedede suggests that he gets it with the drill. Honey, Spikehead and Iroo begin to laugh at Escargoon. But Tiff says to them, "You don't know what the pain's like.". Kawasaki, Gus and Len are also waiting patients. Len uses joke teeth to fool the dentist into thinking he's got toothache. Once Escargoon comes out, they go to Tuggle's grocery store. King Dedede takes things that have a lot of Sugar in them. (The Japanese version has Candy, Chocolate, Caramel, Cookies, Cinnamon rolls, and Melon bread.) Escargoon is concerned about his Majesty's teeth. Dedede thinks that his servant's just jealous because he can't eat all the things he likes. Escargoon asks Tuggle if the toothbrushes are in front of him. The cappy shows him many toothbrushes, including a toothbrush with a rounded disk like tip. But King Dedede thinks that people get cavities by using toothbrushes. In Castle Dedede's dining room, Tuff finishes his tea and then is about to go to bed but Tiff tells him to brush his teeth. When it's tooth brushing time, Tuff brushes his teeth for a few seconds. Once he heads off to bed, Sir Ebrum and Lady Like find that Kirby is still brushing his "teeth".
The next day, both the King and Tuff wake up with cavities. They are sent to the dentist's office. They start arguing about who goes first when Yabui walks out and claims that Dedede has to go first. Dedede tries to escape but Yabui presses a button chaining Dedede to his chair. Yabui then prepares his drill. Dedede gets so scared that he somehow breaks free. He sees a jar of painkillers and eats them all. The pain of the cavity suddenly goes away. Dedede happily walks out of the office feeling better. Tuff goes with him. Later that day, however, the pain returns. Dedede gets so frustrated that he calls NME and orders a dentist monster, Hardy. Hardy, however, does not use numbing, and chases Dedede around the castle. Dedede runs into Tuff and Hardy grabs him instead. Tuff screams in pain, but in few seconds he leaps out, cavityless. It then chases after Dedede. Dedede asks Kirby to fight the monster. Kirby sucks up the monster's drill and becomes Tornado Kirby. Kirby easily blows away the monster. The next day, everyone happily watches Dedede having his teeth drilled.
End of spoilers
Changes in the dub
The wine bottle on the table when Kirby, Tiff, and her family are all eating dinner was airbrushed out in the 4Kids dub along with all the cups of wine's color texture being changed from red to a dark orange possibly to resemble another drink. Oddly, when King Dedede and Escargoon are eating dinner after seeing the dentist, the wine bottle and the cups of wine are left unedited.
The little signature on the poster on the bottom right corner behind King Dedede when he's in Dr.Yabui's office sitting down was airbrushed out but the signature can be seen a few scenes before.
The boss germ's voice differentiated in the Japanese and English versions. In the original Japanese version, his voice sounded rough. In the 4Kids dub, his voice is played in both regular and low pitched tracks at the same time.
When Tuff says that Escargoon should've brushed more often, everyone there laughs at that comment except Tiff. However in the 4kids dub, only Kirby, Tuff, and Honey can be heard laughing.
At the very beginning of the episode, when Chief Bookem is sitting down in one of the seats in Dr.Yabui's office, one can clearly see a poster which looks like a diagram of the interior of a cappy on the wall behind him. But in the next scene, the poster isn't seen at all when it shows everyone in the room and then the poster appears again in the next scene.
Because of how scared young children are at meeting the dentist at first, this episode was removed from the original showing in the US (although it was meant to encourage children to brush their teeth and go to the dentist if they have a cavity). It aired 95th in the US, after The Thing About the Ring.
On the Kirby TV Channel, A Dental Dilemma was the only episode so far to have a scrolling credits instead of one that changes slides.
In the Japanese version, there is one part where Lady Like says that if Tuff goes to Dr. Yabui, then she would buy a CubeGame for him. The CubeGame could possibly be a pun based on the console called the Nintendo GameCube, with the words switched.