YMMV / Dear Dumb Diary

• Accidental Innuendo: Jamie comments that if she was a dog and had to choose between the pound and Angeline, she would choose the pound, unless the third choice was to pound Angeline. Obviously she means hitting her, but "pound" can also mean to have sex.
• Alternative Character Interpretation:
  • Isabella: Jerk with a (VERY hidden) Heart of Gold, or just plain Jerk? Or just a strange girl whose friend constantly exaggerates her personality and stuff she did for comedic effect?
  • Angeline: Is she really a Parody Sue Alpha Bitch, or does Jamie just think she is? Later books seem to be on the latter side: Angeline is a really lovely girl, but she can abuse her power when needed and resents being seen as perfect.
  • Many readers have interpreted Jamie's hatred towards Angeline as actually a repressed crush, because Jamie always describes everything about Angeline as very beautiful and perfect in almost every books in almost every single line, but only describes Hudson, her supposed crush as "the 8th cutest boy in school". Jamie also interacts and has heartwarming moments with Angeline way more often. They think that Jamie actually likes Angeline, but she denies it because she doesn't think she can like someone of her gender, so she tries to dismiss her feelings towards Angeline as hatred.
  • Miss Bruntford's incident upon finally eating some of the school meat loaf herself. Was this a genuine medical emergency that made her realize she needed worse food to be served so the school's meat loaf would look better? Or was she already planning to make the food look better by comparison and faked an emergency to get Mrs. Kelly's food to replace it?
• Designated Villain: Angeline, who from Jamie's point of view, is an Alpha Bitch In Sheep's Clothing. Angeline, presumably, is actually a Nice Girl with shades of Manipulative Bitch or Guile Hero.
• Fanon Discontinuity: A lot of readers prefer to believe that this series ended at book 9. This may be due to book 10 focusing on Emmily to the point of displacement for some and Jamie not demonstrating her growing acceptance of and affection for Angeline from the previous book.
• Fan-Preferred Couple: Despite Jamie having frequent Ship Tease with Hudson, There are quite many readers who ship Jamie/Angeline. It helps that Jamie actually somewhat considers Angeline a friend by the ninth book, and she truly likes Jamie as well.
• Iron Woobie: Dicky Flartsnutt, a Stereotypical Nerd with many allergies who's constantly the target of bullying, but is cheerfully optimistic despite it all, seeing the bullying as just a routine that gives him some social interaction. His attitude seems to come from the fact he has a very loving and supportive family at home.
• Jerkass Woobie: Isabella is a cruel bully, but has a convincing Freudian Excuse as her brothers have been treating her just as badly since she was a toddler. What I Don't Know Might Hurt Me strongly indicates that Isabella could be a nice person if she didn't live on constant high alert due to her brother's abuse.
• Les Yay:
  • As stated above, Jamie constantly draws and describes Angeline in angelic terms and seems quite obsessed with her, constantly talking about how beautiful and perfect she is...and how much she hates her because of that.
  • Jamie often talks about how beautiful her art teacher, Mrs. Anderson, is, and admires her in a manner than resembles a Precocious Crush.
• Older Than They Think: Many people assume that this series was based on Diary of a Wimpy Kid due to their similar premise. In fact, the first Dear Dumb Diary book was published in 2004, three years BEFORE the publication of the first Diary Of A Wimpy Kid book. However, the webcomic predates the first Dear Dumb Diary by two months.
• Periphery Demographic: The books are arguably more enjoyable for older readers who can understand the parodic element to the stories. The series also has its fair share of male fans.
• The Scrappy: Most fans consider Hudson a bland, boring character that adds nothing to the story other than being a shared crush. Even his occasional Hidden Depths aren't considered interesting.
• Tear Jerker: Live Each Day to the Dumbest takes a surprisingly emotional look at grief after Jamie's grandmother (her last surviving grandparent) dies. She spends several pages not even knowing what to write, and breaks into tears when Dad tells Jamie that her mom may now always feel like "a little girl that lost her mom forever." Later, as she goes through her grandmother's things, she feels lost whenever she has a question about the past, then remembers she can't ask her grandparents anything anymore.
• The Woobie: Colette, following The Reveal that, despite being incredibly popular during her time at Mackerel Middle School, has quite a rough time at her old school, suffering a number of embarrassing incidents that become legendary even in other schools, resulting in her having no friends and frequently eating lunch alone.
• Woolseyism: In the first book, Jamie notes how to remember to spell "principal" because her principal is old as a dinosaur, as in "paleontology." In the Spanish version, this joke is done with "director" and "dinosaur."

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