En el estreno de la serie de Disney, los temores de Doug sobre los cambios que están sucediendo en la vida lo hacen pensar en cancelar sus fiestas de cumpleaños. El verano está llegando a su fin y Doug está entregando invitaciones para su fiesta de cumpleaños 12 a todos sus amigos. Mientras él va por toda la ciudad, descubre que Quentington (así como sus amigos) han pasado por cambios. La hamburguesa de corneta se convierte en un restaurante francés llamado Chez Honque, Ruffo es rico, una nueva escuela media se está construyendo, Connie ha perdido peso, Patti está siendo educado en casa por las mañanas y Doug necesita un corte de pelo . Tantas cosas han cambiado que hace a Doug enfermo de los cambios, por lo que cancela su cumpleaños. Pero más tarde, Judy le hace darse cuenta de que los cambios nos hacen diferentes de las rocas, y Doug vuelve a su partido justo a tiempo para algunas noticias impactantes de la Sra. Narinas.

Es el primer día de séptimo grado en la nueva escuela intermedia que todavía no tiene un nombre, así que un concurso de estudiantes "Name Your School" es creado por el ex alcalde White quien ahora es el director de la escuela. El concurso provoca una feroz competencia entre Patti y Doug cuando no les gusta las sugerencias del otro nombre de la escuela

Doug y tito llevan sus uniformes Bluff-Scout a la escuela para prepararse para el próximo Shindiggarama. Doug se ríe y concluye que los Bluff-Scouts son "cosas para niños", así que se retira. Doug comienza a pensar que los deberes Bluff-Scout son pueriles y buscan un ambiente más adulto. Doug entonces intenta vivir una vida más adulta hablando y vestirse como un adulto. Una fiesta madura en la casa de Ruffo le hace darse cuenta de que no se está divirtiendo como un adulto porque le importaba demasiado lo que la gente piensa. Doug vuelve a Bluff-Scouts y se divierte en el Shindiggarama, dándose cuenta de que Bluff-Scouts le ha dado muchas habilidades que necesitará como adulto.

Doug cuenta la historia de lo que ocurrió el verano pasado en un campamento deportivo. La familia Narinas tiene curiosidad cuando Doug recibe una carta de Bolivia. La explicación de Doug involucra al verano anterior, donde Doug fue al Campo de Deportes del Oso Mucho con Patti. Mientras tanto, el asmático camarada de Douglas, Leonard, que ha hecho una carrera para escapar de los campamentos de verano, planea otra escapada. Sin embargo, Doug, Pepe y Patti tienen que preocuparse por el próximo partido de baloncesto que tienen que jugar contra un campamento más duro.

Los idos están teniendo un concierto de break-up. Un problema menor es que Doug no tiene dinero Después de la escuela, se detiene por Swirly para un batido de chocolate, mientras que Patti está con Connie y Roger. A continuación, Doug termina trabajando en Craftee Shoppee de su abuela Edna Después de que Ruffo quiere que venda las entradas, Doug se niega a venderle las entradas. Doug quiere ser rico y le dice a Tito que vaya a la tienda, pero casi olvida invitar a Patti al concierto, enfadándola. Mientras tanto renuncia a Ruffo. En la noche del concierto, Ruffo llega con Patti, Doug está en la colina y es encontrado por Patti. Cuando es difícil escuchar la música, Patti se sienta junto a Doug, y el concierto comienza.

Para un proyecto de clase, Judy deja que Doug le preste uno de sus sombreros de Napoleón teatrales después de hacerle firmar un contrato. Doug pierde el sombrero y Ruffo lo encuentra y no lo devolverá a Doug. Con el fin de recuperar el sombrero de Ruffo, le pide a Doug que haga muchos favores incluyendo robar una vaca de plástico. Después de que todos los favores están hechos, Roger todavía se niega a devolver el sombrero. Puesto que Doug no puede devolver el sombrero a Judy, debe sufrir las consecuencias. Después de que Doug le diga a Judy que Roger no le devolverá el sombrero, Judy toma el sombrero de Ruffo.

For a class project, Judy lets Doug borrow one of her theatrical Napolean hats after making him sign a contract. Doug loses the hat and Roger finds it and won't give it back to Doug. In order to get the hat back from Roger, he asks Doug to do many favors including stealing a plastic cow. After all the favors are done, Roger still refuses to give the hat back. Since Doug can't return the hat to Judy, he must suffer the consequences.

After Connie starts a rumour, the students of Beebe Bluff Middle School get into an uproar that Skeeter is really a vampire. Doug and Roger investigate the rumour and soon everyone becomes scared of Skeeter after they see him hanging out with bats. Soon all of his friends avoid him and on the night of his Halloween party, Doug feels guilty for not going to his party without even knowing what Skeeter thinks about the rumour.

When Doug gets tired of being insulted by Roger and his gang, he gets help from Mr. Dink, who provides him with some home movies of the famous insult comedian, Rick Nickles. After viewing these home movies, Doug gets the ability to crack insulting jokes. At first it puts Roger in his place, but Doug soon realizes that he's made a mistake when he makes wisecracks about the people he loves. Meanwhile, the Beebe Bluff Middle School baseball team goes on strike after Chalky is unfair in his coaching.

It's B.L.A.B.A.B.B.A. Day at the middle school, and there are dozens of clubs the students can join. Doug tris to find the best club and thinks that the Brain Team would impress Patti, and make him less average. Doug then takes the Brain Test and in order to be on the school's Brain Team. When he cheats, he ends up on the team but can't handle studying for the Bowl of Brains Quiz Bowl.

After Doug and Skeeter see a commercial for the new movie Targetman, they desperately want to see it. Soon, all of Doug's friends and even his teachers are talking about Targetman. When Doug tells his parents he wants to see it, they don't allow him because it is way too violent and they feel Doug is not mature enough to see it. So Doug tries to be more mature in front of his parents in order for them to let him see the movie, but they still say no. Doug goes with Skeeter to see the movie anyway, only to regret it later on. Meanwhile, Mr. Klotz is in town to visit Roger who also wants to see Targetman, but Mr. Klotz won't let Roger see it, and he doesn't realize why.

Doug complains to Patti about how tough he has it at home. Doug thinks she must have it easy because she is home schooled. Soon, Beebe and Skeeter and Chalky and Roger debate over who has it hardest. So they all agree to switch places for a day. Also, Moo comes to Doug for advice on his brother who is dying his hair, changing his style of clothes and making friends, and Moo doesn't want his brother to change.

Doug complains that Miss. Kristal gives too much homework, and wishes she wouldn't. After Willy tells his dad that Miss. Kristal is a bad teacher, Principal White fires her. So Principal White becomes their new teacher and brings an end to homework. The class is happy that there is no more homework, but soon Willy is the teacher and when he goes overboard, the entire class realize how good Miss. Kristal was.

With a new baby on the way, Doug's family is too busy to have a traditional Christmas and Doug wants one. So Doug and Porkchop decide to have their own secret holiday celebration in his room. But when he later finds the house completely empty Phil phones with news, the baby is born on Christmas Day. Meanwhile, Fentruck tells all his friends how they spend Christmas in Yakestonia.

Doug finds a lost puppy in Lucky Duck park and he decides to keep it until its owner is found. But the puppy proves to be too much trouble at home. The new puppy may be cute, but he isn't like Porkchop and Doug realizes a regular puppy is a lot of work to take care of. When the puppy's owner is still not found, Doug gives all his friends a chance to own him. Meanwhile, Al and Moo calculate the day an alien is schedueled to land in Lucky Duck Park.

It's student counsil elections at the middle school and Beebe, roger and Chalky are all running. Doug meets eighth-grader Guy Graham who gives him a job on the school newspaper as the cartoonist. Guy tells Doug to create a cartoon on the school student coucil election and draw who he thinks should win. When Roger and Beebe get word, they bribe Doug to make him draw the cartoon about them. Meanwhile, Chad Mayonnaise becomes the middle school's new history teacher and Patti now attends school full day.

When the house of Roger's annoying friend Ned Cauphee burns down, Doug thinks is his fault after telling Ned that ""he'll get his someday"". Theda offers to house him while Ned's house is fixed. When Ned arrives, Doug can't believe how well he behaves because he is nothing like that at school. Doug even starts to feel sympathetic towards Ned. But now Ned is off to visit Grandma Funnie with the rest of the Funnies and Doug is worried he'll ruin his grandmother's home.

Miss. Kristal assigns a book report with no rules, she tells the class to use thier imagination. At the same time, Beebe is being filmed for a documentary sponsored by her Dad. This means the book reports will be shown on TV, which makes everyone in the class want to have the biggest and best report in the entire class. Doug decides to show some drawings he drew, but he realizes that it's not exciting enough, so he goes on a search to find a book where he can make a more exciting report. But when he doesn't have an exciting report the night it's due, he either has to present his drawings or nothing at all.

The new snack fad ""Nic Nacs"" is targeted at adults and kids are going crazy to try some. It soon turns into a negative snack that kids are not supposed to have, which just makes all of Doug's friends wanting some. Through Doug's research for an article for the school paper, he discovers that the snack has an unpleasant and temporary side effect. Also, Mr. Dink quits his job at Bluffco and tries to write his own book.

Guy sees a musical and is inspired by it. He tells Skeeter to work on a secret script for a huge drama play for Beebe Bluff Middle School. The play is a love story between Leonardo da Vinci and the Mona Lisa. Doug gets interested in auditioning when he learns Patti gets the female lead, and is in a KISSING SCENE at the end of the play. Doug trys hard to get the male lead, but when Guy gives himself the role, Doug wonders if his work was wasted. But before showtime, Guy gets sick and someone else has to be the male lead.

Doug finds hair in his comb and fears he's going bald, and figures Patti won't want to hang out with him anymore. The gang also is going to meet at the new water park when it opens and Doug doesn't want to go because of his hair. Meanwhile, Patti gets her first pimple. Beebe gets her first nose job and Roger may have gotten his first whisker. Doug lets all these things get in the way of his fun, and later realizes he shouldn't have. Also, Skeeter gets his first failing grade in shop class when his coat rack assignment isn't simple enough, so he is given a second chance to make another simple object.

Doug begins to worry that the new baby Cleopatra Dirtbike will end up being another Judy, and Judy is afraid she'll grow up to be like Doug. So the two set out to shape the baby's personality. When Phil and Theda go out for an evening, Judy and Doug are left to babysit and don't want the other to be left alone with Dirtbike. But when their fighting leaves Dirtbike alone in Mr. Dink's house, they realize they are going to have to co-operate to get her out.

Doug wakes up the morning after the Flounder's Day Picnic to find that Porkchop has packed up his things and is gone. He concludes that someone must have done something bad to him to make him pack up and leave. So he goes to talk all his friends to question them about what happened to Porkchop the day before.

Doug enters a school contest to paint a mural on a new school wall. But when he has to share the mural design with Roger, he's not sure he can do it with him because he thinks Roger can't really draw. Also, Bluffington is in a heat wave and the Sleech twins think it is their fault, so they set out to change the hot weather.

Doug and his friends decide to meet at Funkytown and spend a day having fun, so Judy volunteers to drive him there. But before she drops Doug off, Judy wants to shop at Snord Grupen. After leaving the giant mall, Doug and Judy get lost on the way to Funkytown.