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Dear Dumb Diary is a series of children's books written by Jim Benton (also known as the guy who created Happy Bunny). The books are presented as the diaries of Jamie Kelly, a middle-school girl with a very interesting view of the world.

The books, in a nutshell, are a mixture of Xanatos Gambits, strange events and humour just sailing on Rule of Funny, and frequent deconstructions and parodies of common School Tropes. The main character, the unpopular brunette, is a rather selfish and mean-spirited girl (this goes quadruple for her best friend Isabella), while the so-called Alpha Bitch Angeline is consistently shown to be kinder, smarter and a more supportive friend. The three girls spend their seventh grade year getting into wacky situations, whether it be (supposedly) haunted pants, student-teacher creepy crushes, money-raising schemes or teacher's relationships, often at the hands of a plot built by Isabella. In the end, Jamie learns a valuable lesson (though it may not be the one you'd expect).

As of the 10th book, Jamie has now finished her six years of the seventh grade.

Books in the series (so far):

  • Let's Pretend This Never Happened
  • My Pants Are Haunted
  • Am I the Princess or the Frog?
  • Never Do Anything, Ever
  • Can Adults Become Human?
  • The Problem With Here is That It's Where I'm From
  • Never Underestimate Your Dumbness
  • It's Not My Fault I Know Everything
  • That's What Friends Aren't For
  • The Worst Things In Life Are Also Free
  • Okay, So Maybe I Do Have Superpowers
  • Me! (Just Like You, Only Better)
  • School. Hasn't This Gone On Long Enough?
Tropes used in Dear Dumb Diary include:
  • The Ace: One book's plot is essentially about an Ace showing up: somebody who (by Everyone Looks Sexier If French) is prettier than Angeline, more vicious and destructive than Isabella, and more spontaneously artistic than Jamie. She eventually turns out to be a legendary outcast who rendered her school uninhabitable in a desperate gamble to go somewhere nobody had heard of her and make friends.
  • Alpha Bitch: Angeline... according to Jamie, anyway. Of course, she has no clique, hangers-on or regular friends (until you can count Jamie), is friendly to all the school "losers", shows no concern over her social status, and while an excellent manipulator, uses said power rarely and generally "for good".
  • Berserk Button: Do not make fun of Isabella's name. Or the shape of her head. Actually, don't make fun of Isabella in general.
  • Beautiful All Along: Parodied on two separate occasions. The first time, Jamie and Isabella give a makeover to an unpopular girl named Margaret and as a result, end up becoming Unwitting Pawns in another girl's Xanatos Gambit. The second time, it turns out that the only reason Jamie isn't considered pretty is her unflattering hairstyle.
  • Big Brother Bully: Isabella's two older brothers, although she has gotten more than her fair share of revenge.
  • Bitch in Sheep's Clothing: Angeline shows signs of this before it's revealed that she has Hidden Depths.
  • Characterization Marches On: In the first few books, Angeline was more like a stereotypical popular girl, and Isabella was spacey and awkward instead of cunning and manipulative.
  • Chekov's Gun: Being surprisingly tightly plotted is one of the strong points of the series. It's a good bet that everything is one, and trying to figure out just how some offhand comment or minor event is going to recur and become a plot element is a good part of the appeal to adults.
  • Cloudcuckoolander: Jamie.
  • Cool Big Sis: Carol is technically Jamie's aunt, but she fits otherwise.
  • Deadpan Snarker: Jamie, so freaking much.
  • Diary: Well, duh.
  • The Ditz: Emmily. Poor, sweet, clueless Emmily.
  • Exact Words: When the gym teacher says each group needs to get a plastic baby across the gym without them touching the floor and throwing the baby is not allowed, Isabella uses the rubber snake they've been given to launch the baby instead.
  • Getting Crap Past the Radar: This is a literary form of family entertainment, meaning it's good to read to kids and won't bore the reader.
  • Grotesque Cute: Jamie's drawings sometimes fall into this.
  • Hair of Gold: Angeline.
  • Hot for Student and Hot for Teacher: The Squick inherent in these tropes is lampshaded in the third book.
  • I Have Brothers: Parodied (and taken Up to Eleven): "She has brothers" is basically Jamie's reasoning behind why Isabella is an Ax Crazy Manipulative Bastard.
  • Jerkass: Isabella.
  • Jerk with a Heart of Gold: Jamie and (possibly) Isabella.
  • Kids Are Cruel: Or at least very shallow. The characters ARE in middle school where reputation is everything and can be destroyed over the smallest things.
  • Lethal Chef: Jamie's mother (except when she's making hors d'œuvres).
  • Literary Agent Hypothesis
  • Manipulative Bastard:
    • Isabella, almost to the point of parody.
    • In much quieter (but equally effective) fashion, Assistant Principal Devon and his niece Angeline have their moments.
  • Mind Control: In two books, some way to control people's emotions and attitudes through scents is plot-significant, and seems to go a bit beyond Jamie's fertile imagination. A common early example of Jamie's imagination is her momentarily falling under Angeline's "evil spells", with descriptions almost bordering on self-Foe Yay.
  • Mystery Meat: Apparently, this is all the school cafeteria serves on certain days.
  • Nerd Glasses: Isabella. Don't mention them.
  • The Nicknamer: Mike Pinsetti. This is eventually revealed to show Hidden Depths: he's one of the most poetically inclined boys in that grade.
  • Parody Sue: Angeline, though the sixth book shows that she could also be considered a Deconstructed Sue. The first couple of books may be one of the more complete subversions of the Canon Sue trope in literature. Jamie starts out obsessing about how Angeline is so obviously a Mary Sue (not by trope name) and how every little thing that happens is clearly all about Angeline. In fact, Angeline's only real relevance in the early plots is actually caused by this obsession. She only has the narrative spotlight because the protagonist is constantly throwing it at her.
  • Popular Is Dumb: Averted by Angeline.
  • Precious Puppies: This eventually becomes a plot point.
  • Punny Name: Hudson Rivers.
  • Running Gag: The Mystery Meat, Wheretheheckistan[1], Jamie's mother's horrible cooking, Jamie's hair, Angeline's apparent Sueness, Isabella doing horrible things to her older brothers, etc.
  • Rule of Funny
  • Shallow Love Interest: Hudson Rivers exists so Jamie and Angeline have a guy to fight over. He eventually proves to be even more shallow than that, when it turns out he has a crush on (and would be a decent match for) Isabella.
  • Sitcom Arch Nemesis: Angeline thinks of Jamie and Isabella as friends and either isn't aware of their scorn for her or just ignores it. It takes Jamie eight books to realize this.
  • Stalker with a Crush: Jamie, toward Hudson Rivers.
  • Suddenly Always Knew That: Almost a Running Gag. At the end of a book where a skill is plot-relevant (speaking a foreign language, playing guitar in a band, maintaining an automobile), it tends to turn out that Angeline had said skill the whole time and didn't bother to mention it.
  • Take That: The Whisker Brothers, a three-boy band whose lyrics seems manufactured to make a middle school girl like them. Sounds like The Jonas Brothers.
  • Toilet Humour: Recurs. In particular, Jamie's dog Stinker is a magnet for this type of joke. As often as not, Stinker's bodily functions even drive the plot.
  • Token Evil Teammate: Isabella has no trace of empathy and a very utilitarian concept of friendship. In fact, it's safer not to be her friend because -- well, it's safest not to be anywhere near her. She is still unquestionably a True Companion.
  • Uncatty Resemblance:
  • Unreliable Narrator
  • Vitriolic Best Buds: Jamie and Isabella are type 2, Jamie and Angeline are type 1.
  • What Do You Mean It's Not Awesome?: The series practically runs on this.
  • X Must Not Win: The instance of deliberately sabotaging one's own campaign to split the vote shows up in one book (it works perfectly... and still doesn't turn out at all the way it sounds).
  • Xanatos Gambit / Batman Gambit: Once per book.

Notes

  1. Jamie's catch-all term for any country that she doesn't care about
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