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Dear Dumb Diary — by Jim Benton
Dear Dumb Diary Series in Order: 18 books
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Let's Pretend This Never Happened
Book - 1
PERFECT GIRLS MAKE PERFECT ENEMIES Dear Dumb Diary, School was okay today. Actually, it was better than okay. Angeline got her long, beautiful hair tangled in one of the jillion things she has dangling from her backpack, and the school nurse -...
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My Pants Are Haunted!
Book - 2
HAIR. BEAGLES. JEANS. IT NEVER ENDS. Dear Dumb Dairy, Anyway, Isabella said it wasn't the makeover that boosted Margaret's popularity and forced us down. It was the pants. She said it wasn't my loud "yahoo" in science that got me switched again s...
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Am I the Princess or the Frog?
Book - 3
LOVE IS IN THE AIR. SO YOU MIGHT JUST WANT TO STAY INSIDE. Dear Dumb Diary, I got another poem today from You -- Know -- Who ... She is the fairest blossom, true, She blooms in any weather. But I must love her from afar. We'll never be t...
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Never Do Anything, Ever
Book - 4
BEAUTY IS ONLY SKIN DEEP, BUT HATE GOES ALL THE WAY TO THE BONE. Dear Dumb Diary, Isabella said that she got the information about this charity online and I could help her collect for it if I wanted to, so as we made the rounds for the clothes, w...
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Can Adults Become Human?
Book - 5
Read the hilarious, candid (and sometimes not-so-nice), diaries of Jamie Kelly, who promises that everything in her diary is true...or at least as true as it needs to be.Dear Dumb Diary,My social studies teacher, Mr. VanDoy, never smiles. I know tha...
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The Problem With Here Is That It's Where I'm From
Book - 6
THERE'S NO PLACE LIKE ELSEWHERE. THERE'S NO PLACE LIKE ELSEWHERE. THERE'S NO PLACE LIKE ELSEWHERE. Dear Dumb Diary, Beautiful glorious news! Today they told us that something went stinkfully wrong with the heating or ventilation system or something ...
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Never Underestimate Your Dumbness
Book - 7
MAY THE DUMB BE WITH YOU Dear Dumb Diary, Isabella is probably right. She almost always is. When I think back on all the things I've seen Angeline do, the one thing they have in common is that they're all dumb. (They're all strawberry-scented, to...
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It's Not My Fault I Know Everything
Book - 8
New York Times Bestselling author Jamie Kelly is back with another hilarious, candid, and sometimes not-so-nice diary!Dear Dumb Diary,I went back and read some of my very oldest diaries. The entries say things like "I eated salad dressing" and "I got...
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That's What Friends Aren't For
Book - 9
Dear Dumb Diary, So now I'm friends with Angeline. This is automatic friendship, and I have to just accept it and make the best of things. See, if I objected, then Aunt Carol might divorce Angeline's uncle, sending both of them tumbling into a ...
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The Worst Things in Life Are Also Free
Book - 10
School's out for the summer, and that means no more Meat Loaf Thursdays, Sunday homework-cramming, or teachers (unsuccessfully) trying to act cool. It also means that certain Mackerel Middle Schoolers have a lot of time on their hands . . . and serio...
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Okay, So Maybe I Do Have Superpowers
Book - 11
Something strange is happening at Mackerel Middle School. Jamie can suddenly and inexplicably understand the weirdest and most mysterious creatures around: boys. And there's only one logical explanation--superpowers....
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Me! (Just Like You, Only Better)
Book - 12
There are more than 5 million Dear Dumb Diary books in print! Bestselling author Jamie Kelly is back with an all-new, all-funny diary! But she has no idea that anybody is reading it. So please, please, please don't tell her. Dear Dumb Diary, ...
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School. Hasn't This Gone on Long Enough?
Book - 13
Dear Dumb Diary is a hilarious hit! Now after 12 books (each covering a month of her life), Jamie Kelly's upcoming diaries have a fresh look and a fun twist. It's Dear Dumb Diary: Year Two! The diary entries are still laugh-out-loud funny -- but this...
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The Super-Nice Are Super-Annoying
Book - 14
Do NOT read Jamie Kelly's top-secret diaries! "Sometimes it amazes me how ingenious I am about everything." --Jamie Kelly We've been with Jamie Kelly through her search for inner beauty, poofy bridesmaid dresses, and desperate attempts to make ...
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Nobody's Perfect. I'm As Close As It Gets.
Book - 15
Whatever you do, DON'T read Jamie Kelly's bestselling diaries! The bestselling Dear Dumb Diary series is a hilarious hit! Now Jamie Kelly's diaries have a fresh look and a fun twist. Dear Dumb Diary Year Two is still laugh-out-loud funny -- but ev...
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What I Don't Know Might Hurt Me
Book - 16
Dear Dumb Diary, Just when I was pretty sure we could let the Student Awareness Committee quietly die a dignified death like some majestic old elephant or the Square Dancing Club, Angeline has to be aware of something. Great. And, of course,...
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You Can Bet on That
Book - 17
The hilarious and bestselling series from Jim Benton continues! Jamie, Isabella, and Angeline have known each other for a long time. They've even become friends -- whether Jamie likes it or not. But when the trio starts a friendly competition, all...
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Dumbness Is a Dish Best Served Cold
Book - 18
Jamie Kelly is back and dumber than ever in this super-deluxe four-color Dear Dumb Diary special edition! Life at Mackerel Middle School is as dumb as ever -- but Jamie Kelly may have finally found the key to fame, fortune, and fabulousness. Toge...
Series Premise
The core premise unfolds through Jamie Kelly's first-person diary entries, where she chronicles the daily disasters, triumphs, obsessions, and petty grievances of middle-school life at Mackerel Middle School. Jamie pours out her unvarnished opinions on everything from crushes and cafeteria food to teachers, popularity contests, and the unfairness of the universe, often exaggerating wildly or twisting events to suit her dramatic worldview. She promises that everything is "true... or at least as true as it needs to be," which gives her license for hilariously unreliable narration. Plots revolve around school events—science fairs, fundraisers, class elections, visits from relatives, or schemes to gain popularity—while Jamie navigates friendships, rivalries, family quirks, and her own insecurities with a mix of scheming, whining, and accidental insight. Each book delivers standalone episodes packed with absurd mishaps and Jamie's signature snarky commentary, always ending on a note of reluctant self-awareness or grudging growth.
Dear Dumb Diary Series Reading Order
🟡 Mostly Standalone · Start Anywhere
Mostly standalone stories with recurring characters in a shared setting.
The series can be read in any order, as the books are largely episodic and standalone. Each entry focuses on a self-contained slice of Jamie's life with fresh predicaments and resolutions, and the core cast and setting remain consistent without requiring prior knowledge. There's no overarching plot arc or major character progression that demands sequence—Jamie stays perpetually in middle school, dealing with similar tween issues. That said, reading from the beginning offers the joy of watching recurring gags, inside jokes, and subtle evolutions in relationships feel more rewarding, but it's far from essential; kids happily jump around without missing a beat.
Explanation of reading order types
Dear Dumb Diary Series Characters
At the center is Jamie Kelly herself, a snarky, dramatic, occasionally self-centered seventh-grader who narrates with unfiltered candor. Observant, quick-witted, and prone to exaggeration, she obsesses over popularity, crushes (especially on Hudson), and avoiding humiliation while secretly caring deeply about her friends and family. Her best friend Isabella Vinchella is bold, hotheaded, manipulative when it suits her, and fiercely loyal—often the instigator of schemes with her tough exterior shaped by older brothers. Angeline, the beautiful, popular, seemingly perfect girl, starts as Jamie's perceived nemesis but reveals herself as genuinely kind, charitable, and human—leading to a complicated frenemy dynamic that evolves into real friendship. Jamie's family includes her patient mom and dad, plus occasional appearances by annoying relatives like her troll-like little cousin. Teachers, classmates, and minor figures (like crush Hudson or various school staff) rotate in for comic relief.
Setting of the Dear Dumb Diary Series
The setting is the familiar, slightly exaggerated world of Mackerel Middle School—a typical American middle school complete with lockers, cafeterias, gym classes, school buses, and the relentless social hierarchy of tweens. Everyday locations like classrooms, hallways, the lunchroom, and Jamie's home provide the backdrop for chaos, with occasional field trips or family gatherings adding variety. The environment feels authentic yet cartoonishly heightened through Jamie's lens—teachers become tyrants, popular kids become mythical beings, and minor incidents balloon into epic sagas.
Tone & Themes of the Dear Dumb Diary Series
The tone is irreverent, sarcastic, and gleefully exaggerated, full of over-the-top drama and brutally honest (sometimes mean-spirited) observations that ring true to the middle-school mindset. Benton's humor is sharp and self-deprecating, leaning into gross-out moments, petty jealousies, and absurd logic without ever turning truly cruel or dark—it's cathartic comedy that lets readers laugh at the ridiculousness of growing up. The writing crackles with witty one-liners, doodled asides, and Jamie's signature flair for hyperbole. Themes center on the universal pains of adolescence—fitting in versus standing out, friendship's complications, the sting of embarrassment, envy of "perfect" people, family annoyances, and the slow realization that maybe you're not always the hero of your own story. Underneath the snark lies gentle messages about empathy, self-acceptance, and the idea that everyone feels awkward sometimes, delivered with zero preachiness.
In the end, Dear Dumb Diary endures as a wickedly funny mirror to the messy, mortifying magic of middle school, where every disaster feels world-ending until it doesn't. Jim Benton captures the raw, hilarious truth of being a kid on the cusp of growing up—full of schemes, grudges, and secret hopes—with such spot-on wit that readers can't help but laugh, cringe, and feel seen. The series reminds us that dumb days make the best stories, and that behind every dramatic diary entry lies a heart figuring things out, one embarrassing moment at a time. It's the kind of reading that turns reluctant kids into avid fans, proving that honesty—even the brutally dumb kind—is the ultimate superpower.
Books in this series fall into the following genres
Genres
Themes