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Greg becomes rich and famous...as a writer, a cartoonist and a video game designer.
Greg's always talking about how he wants to be rich and famous when he grows up, and based on a WMG below, he seems to enjoy writing in his journal(s) as the series goes on, so maybe he's developed a passion for writing and drawing in addition to stuff like video games.

Greg has begun to start really loving writing in his journals
Two points back this up. First, Greg spends the first two books complaining about having to write in a journal, especially with the hardcovers having the word "diary" written on them, but later stops. Second, the journals began spanning shorter period of time, the first being a year, the next two being half a year each, and now we have weeks condensed into books. Therefore, one can only assume that Greg has loved to do the thing that annoyed him and is trying to squeeze down every bit of his life on paper.

So on the bright side, Greg in universe may be a fledgling writer.

The book is secretly meant to be an in depth psychological study of how a sociopath sees the world at a young age
It would explain why Greg only shows empathy for himself, the fact that his books are spanning shorter periods of times (he wants every bit of his life to be known to the world), and why bad things keep happening. While one could argue that the Sadist Show tendencies are meant to be played for commentary on suburban American life, statistically Greg's life should not really have that much drama in it. Therefore, one can assume that Greg believes the world is out to get him and is making up or exaggerating real world events.

Helping this guess are the movies, which are far less bleak and show all characters (even ones Greg hates) more positively. It also eases some of the Too Bleak, Stopped Caring reactions the book struggles with if we realize we're meant to laugh at how a self centered person sees the world, like at how we laugh at celebrities prone to Wangst.

Greg is a sociopath
Greg rarely shows empathy for anyone but himself, and almost never feels sorry for all of the obnoxious and/or cruel things he does to people. He also constantly manipulates his family and "friends", especially Rowley, and one gets the impression he only sees them as tools to facilitate his own gratification, for example, he constantly takes advantage of Rowley's childlike mind, tricking him into doing things for him, or taking (or at least sharing) the fall for something that is entirely Greg's fault.Greg also seems to be rather smart for his age, he can read people easily and play on their emotions and personalities. He probably WILL be successful when he reaches adulthood, in Politics or some other field that requires ruthlessness.
  • He has done some nice things, like taking the punishment himself for the Green Blob incident, and trying to play with Manny (though Manny always ruins it by getting Greg in trouble, although they did huddle together in the terrifying tunnel slide at Corny's.) Oh, and he decided to hide the diamond ring so the family couldn't get into a fight over it. As well as that, he's comforted Rowley after a bad breakup, become genuinely angry because a Nice Guy got detention, and is disgusted by two dropouts and their gang stealing thousands of old science projects and papers so they can sell them off to make a quick buck or ruin the awesome Hero Points scheme.

The books are Greg's exaggeration, and the movies are what actually happened.
The books have Greg be less of a Jerkass and makes the tales of abuse even more abusive. He also cuts parts he doesn't like (like getting beaten in wrestling by Patty Farrel). The movies are the true story of what happened. Example: In the book, Greg frightened the little children with a worm. In the movie, Greg says that aliens are going to eat them, and abandons them in a construction pit. IN THE RAIN.
  • Actually, he's more of a dick in the book; in the movie he had a reason to do that (He thought a bully from earlier was approaching)
  • Yeah, he's a much nicer guy in the movies - I'd call the movies the exaggeration.
  • Given how many liberties the films take with the source material - not to mention a glimpse into Greg's diary in the Rodrick Rules movie shows Chirag disguised as Holly, which didn't happen in the book - it's more likely that the books and the films (and the webcomic, for that matter) simply take place in alternate universes.

Manny will grow up to become a Psychopathic Man Child Serial Killer
As of book 6, Manny is starting to show an alarming Lack of Empathy and enough boldness to start openly bullying the other members of his family. He's standing right on the edge of Creepy Child territory, and, in light of this, it wouldn't be all that surprising to see him wind up as a temper-tantrum-throwing, thumb-sucking murderer a few years down the line.
  • The first several books do show that Manny's parents spoil him incredibly rotten, much to Greg's chagrin.

The books are actually complex social commentary on the state of America's educational system.
Yes, a teacher not knowing how "jolly" is correctly spelled and an eighth grader not knowing how to carry in math could both be chalked up to Rule of Funny, but some of the events in Greg's school hit too close to home for many students for it all to be exaggeration.
  • Not just the school system. The entire culture of childrearing of today. Think about how Manny is being babied. And Greg's comments on how Rowley's parents shouldn't give him prizes just to feel like winner. And Susan, the Moral Guardian.

Manny is autistic

The whole hot dog issue in Cabin Fever, plus he doesn't seem to be maturing. Not to mention he's young but smart enough to turn off power in the entire house except his own room.

  • Book 7 had possibly shown more evidence, since he's been said to have terrible social skills for his age, and doesn't like playing with other kids and would rather play independently. He also has not one, but almost a dozen imaginary friends. Of course, it's still too early to tell if Manny has autism since many traits between normal and autistic preschoolers are shared and you don't notice any symptoms until later in childhood.

Greg's Dad spent the blizzard in the hotel with his mistress

Dunno, it just seemed odd that he would say he couldn't get home.

Greg (in the movie at least) was the one who wrote on the door

The handwriting on the wall matches up with Greg's. In the book where it shows a cartoon he drew of the incident, this can be easily explained as artistic interpretation. In the movie, however, the only explanation is Greg did it. Perhaps something illicit was brought to the party and Greg imbibed. Under the influence, Greg started to think his brother was a really cool guy and thought it would be nice to write "Roderick rules!" on the door in black magic marker. He has no memory of this event.

Frank (Greg's dad) thinks that Greg is gay and does not approve.

Greg acts really feminine and flamboyant at times; caring for a baby doll as if it were his own child, saying that he'd choose water jazz over swim team, not liking sports and other "manly" things, etc. Perhaps Frank suspects that Greg is gay, and is trying to "stamp it out of him," hence why he throws away said doll without asking, refuses to listen when Greg expresses dislike of sports, tries to send him to military school, and other things like that.

  • This is also backed up by the fact that Frank doesn't approve of the Barbie doll Greg gets for Christmas.
Manny is actually a very smart kid.

He's definitely smart enough to know how to work the electricity in the house and appears to know that his mom accepts "I'm only thwee!" as an excuse. He's simply Obfuscating Stupidity and pretends to not be maturing because he knows that as long as he acts childish and throws tantrums, he'll always get his way. Manny, you Magnificent Bastard.

Manny has OCD.

Think of how he wanted his sandwiches cut JUST RIGHT, and how he wanted his hotdog to have the mustard in a PERFECT LINE.

In The Third Wheel Greg and Holly will be an offical couple.
In the third movie that's what happened so it doesn't seem unlikely.
  • Jossed, Holly doesn't even show up at all.

In The Third Wheel Greg's Date To The Dance Will Be Patty
Somehow, he'll either be really desperate or forced into taking her and will have a hilariously terrible time. As consolation, the author will have him hook up with Holly afterward (in line with the above guess).
  • Jossed, he gets a date, but then Rowley steals it from him. Poor Greg.

In a future movie Bryce Anderson will be the main antagonist.
He is featured in the past three books and the third movie ends with Greg and Holly becoming an official couple. Holly herself isn't part of the main plot in The Third Wheel but it is mentioned that she likes Bryce in that book. Now in line with the WMG that the movies are the true events and the diaries are exaggerated, it could be that in the films universe Greg and Holly where not in good terms in their new relationship, so he didn't write her in his diary at the time. If a movie adaption of The Ugly Truth Cabin Fever or The Third Wheel is made Bryce would probebly be a Romantic Rival to Greg.

Holly & Chirag are actually Emma & Ravi.
Chirag's rivalry with Greg over Holly is actually an example of My Sister Is Off-Limits… though it doesn't explain why Holly is quite a bit smarter than Emma.

The Last Straw was supposed to be the last book in the series.
As with most other trilogies, the book ends on a high note, and the last page says in large text "THE END". Furthermore, the next books try to stretch shorter and shorter timeframes into a 200-page graphic novel. Case in point: The Third Wheel takes place over several weeks, yet is just as long as the first book, which takes place over a year. Perhaps someone at the publishing company saw how well the books were selling and decided to make the author write more.
  • Actually, I do remember hearing about something like this.
  • This theory also explains why Trista was put into the series, only to be jettisoned from it at the very beginning of the next book; Kinney had originally not planned on there being a next book; Trista was likely just put in there so that the series would give Greg a Happy Ending even though he didn't get Holly Hills.
  • Its title certainly would indicate it.
  • That was how the orginal webcomic ended, and since the first actual book came out, the author said there would be more after all of the webcomic is covered. So it was most likely planned the whole time.
  • Continuing with the shorter time frames, it'll go from months, to weeks, to mere days, and then maybe the 22nd book will try to stretch out a 60 minute period into a 200 page book.
  • According to Fun Brain at one point, Jeff Kinney stated the series was supposed to be 5 books long and the last two wouldn’t use material from the webcomic, hinting at the fourth instalment being summer-themed (which still happened).

The series will go on for a really long time.
The series will officially end when Greg and Rowley are in college.

Related to the first theory, Greg has clinical narcissism.
He shows quite a few signs of narcissism, particularly as the books go along. They include but aren't limited to:
  • Blaming all his problems on others.
  • Not caring about others except as a method of personal gain.
  • Not caring or taking responsibility when he hurts others.
  • Becoming seemingly unable to process the embarrassment, sadness, or pain of others.
  • Harming others intentionally and only showing signs of remorse or regret when he's punished.
  • Having no real friends, and only caring about having real friends as a way to make himself feel better.
  • Expecting others, particularly his family, to do whatever he wants without contributing at all.

Greg will be in high school by book 10.
I was thinking about how Greg has to have been in middle school for more years than usual by now. But then it hit me: by the end of the 8th book, Greg is probably in April or May of 8th grade. If you think about it, this means that the 9th book will be about whatever happens in the last bit of 8th grade, and the 10th will be high school. Considering the 5th book is about Greg's aging, he's not just going to stay in middle school forever.
  • Jossed, at least for now.

    • Partially lampshaded in book 10: Greg says that he feels like he's been in middle school forever.

    • It's a crazy theory, but what if Greg was held back and just isn't talking about it due to being an unreliable narrator?

      • That would mean that any old classmate who is still his classmate was held back as well.

The series will end on a dark note.
Either with Greg killing his family, committing suicide, or both.
  • OK, that's a bit too brutal for a series aimed at primary-school kids. Maybe something more of Greg running away forever would suffice, but not after leaving his journals at school so everyone can read them and see how much his life sucks (in his opinion.)
  • I for one, would rather personally have him move out of the house.
  • Maybe the ending could make it ambiguous as to whether Greg committed suicide or just ran away.

Greg will at least have one wish come true for him-he gets to date Holly Hills (in the books.)
Because really, the guy's a pretty big jerk, but he does need something happy once in a while. Oh, and it could create an interesting situation-all those things Greg did to help out Heather earlier? Well, Heather could have told her younger sister (a few books later) "Hey, that Greg Heffley is a pretty nice guy-he stops me from getting bored with all the cool stuff he says, and he saves me work, too! Maybe you could try and go out with him? I know that he's a dork, but see how it goes!"

The book will have Susan and Frank Heffley and Mr. Jefferson and Mrs. Jefferson start becoming the only sane people. Holly discovers how much crap Greg has gone through and becomes his girlfriend. Rowley gives Abigail "The Reason You Suck" Speech and Manny is sent to a mental institution and Rodrick is sent to jail for two months.

Frankie is Greg's dad
In the tenth book, at a camp, there is a rumor about a madman named Silas Scratch, and the chaperon (who is about the same age as Greg's dad) says that when he was a child a boy named Frankie discovered Silas's shack and was never the same again. Later we find out the shack is actually a shed and Silas doesn't exist, Greg's dad as a kid discovered the shed and lied so the others wouldn't hog it. And we do know Greg's dad is called Frank. The only difference is the "i-e"
  • Really, it was pretty much confirmed that this was the case.

Frank Heffley is not Manny's biological father
Manny's physical appearance looks completely different from anyone in the Heffley family. So it's possible that Susan Heffley might have had a secret affair.

Greg has ADD or ADHD
I have ADD and I've always thought that he had ADD. He displays a short attetion span and is clearly smart but doesn't work hard.

Rowley is better-looking than he is portrayed
Otherwise, the ease with which he wins the sympathy of girls would be puzzling.

Expanding on the above, Rowley is actually something of The Ace
Rowley is actually a kindhearted, friendly, charismatic and talented kid who is slightly naive for his age due to his sheltered upbringing. Greg just plays up his one negative trait and completely ignores his positive ones when talking about him because he's jealous.
  • I regret not thinking about it myself. After all, he had a girlfriend before Greg did, and after he and Greg "broke up" in book 1, he was the first to find a new best friend.

Future books will have some actual Character Development for everyone and good moments for Greg.
Frank Heffley will become less of a Jerkass, Susan Heffley will stop being clueless, Manny will become less of a Spoiled Brat, Rodrick might start heading towards his movie counterpart's personality, and Greg will not only become less of a jerk but will have some genuine, long-lasting Pet the Dog moments directed towards him, and will be subject to more good fortune than misfortune.
  • There might even be a book where he blows the whistle on the bullying problem at his school

The series will end on a light note
  • Combine this with the Character Development and the series could end with Greg being hooked up with a publisher and his books become popular.

The series will have the Heffleys go through a major shake-up or two
  • Greg is diagnosed with cancer and the whole family comes together to help Greg beat cancer.
    • The Ugly Truth had Greg witness his grandfather smoking so there is a chance that he could develop secondhand cancer
  • Or Greg is diagnosed with ADD and ADHD and Gerg reaps the benefits of special education including no homework, and bully protection.

Greg is haunted by a bad luck spirit.
It does everything in its power to make Greg's life as hilariously miserable as possible.

Jokes featured in The Getaway
An obvious one with a Screaming Plane Baby, the Take That! to airline food.
  • Confirmed. Greg is seated with a baby that throws tantrums, and he is displeased when he receives a pack of pretzels as a snack.

The series' final book will involve other characters finding Greg's diaries.
Subsequently, he will have a ton of things come back to haunt him at once, including the water park locker key and the diamond ring.

Greg is planning to sell his journals once he becomes famous
In the first book, he agrees to start writing journals because he doesn't want to waste time answering questions about his childhood when he becomes famous. Sometime after that, he realizes something: why give them away for free when he can make more money off of them? This also explains why he stops complaining about his mother making him write the journals, and why the journals began spanning a shorter period of time: a shorter timespan per journal means more journals, and more journals mean more $$$.

Albert Sandy is just really gullible
There's this boy in Greg's class named Albert Sandy who spouts outlandish claims. The Wiki says he's lying and he might be, but he often says that he heard or read it somewhere or watched a movie, and his claims (like girls don't fart, we only use ten percent of our brains, etc) are often rumors that get passed around on the playground and in other places, so maybe he actually believes those things.

There will be a future book where Greg will blow the whistle on his school's bullying problem and would be rewarded for coming forward but Greg's school faces disastrous consequences
  • It would start with Leon Ricket (from Book 3) attacking Greg on his way home and he is sent to a hospital and he tells him, mom, what happened and the person who attacked him, he even tells her about the bullying that goes on and that this attack would never happen if the school had a "zero-tolerance policy" towards bullying. Greg then tells Susan to tell the principal of Greg's school that they should try a "zero-tolerant" approach towards bullying. Susan then tells Mrs. Mancy the principal of Greg's school and she has Leon suspended for thirty school days (the maximum length a student can be suspended for in Greg's school) and announces that the school will implement a "zero-tolerance policy" towards bullying and that students who are caught bullying others will be suspended, and Greg would have his slate wiped clean and not just reinstated as a Safty Patrol but as the commissioner. However, in the middle Greg begins to see the damage that the "zero-tolerance" approach is doing to the suspended student's grades and tries to lobby leniency for first-time offenders and those to commit minor offenses but fails to. Near the end, this "zero-tolerance" approach has a disastrous consequence when all the bullies cheat on the standardized test this causes the school to scale it's "zero-tolerance" policy way back. the bullies are sent to juvenile detention. The principal would have to face the state board of education and wished she'd listened to Greg. The whole school will retake the test under strict monitoring. The state board of education votes to sanction Greg's school to only give it minimal funding and has to cut all after-school activities and it's summer school program and Greg would ultimately keep his job and says that the "zero-tolerance" approach made everything worse and how it's basically just an excuse to have students suspended, and that if he were to choose between being suspended and getting detention would take detention over suspension any day.
  • You can write a fanfic out of it!

The books are set in Massachusetts

I know that the books aren't really meant to be set in any specific location. I know that the reader is supposed to believe the stories could happen anywhere. However, the books present some clues to where they take place. First, given the traditions the characters practice (methods of celebrating Christmas, Halloween, and Thanksgiving), you know they live in the United States. Second, in the Dog Days book, Greg says that his dad had to drive four hours round trip to pick up Greg from Rowley\'s family\'s beach trip. This means that the beach is two hours\' worth of driving distance from the beach, so the Heffley family must live on either the West Coast or the East Coast. Third, they have to deal with snow. Heck, the whole premises of Cabin Fever and The Meltdown are centered around bad snow conditions! And, finally, in The Third Wheel, Uncle Gary says he met a guy in Boston, and that\'s where he got his Botson T-shirts from. Now, the only U. S. city named Boston is in Massachusetts, and based on what Greg says about Uncle Gary\'s financial situation, it doesn\'t seem likely that Uncle Gary would make a bundle in someone else\'s business, basically go broke in the process, and then fly somewhere else to find \"a place to stay until he can get on his feet again.\" Massachusetts fits all of the criteria I have described here.

  • This could actually be the case, as Jeff Kinney does in fact live in Massachusetts.

Greg is over-exaggerating things just to make his life sound even more exciting

If you consider that Greg is the Unreliable Narrator of the series who describes the events that'd happened to him and others, this theory would make sense. Think about it, the part in Old School where the pig suddenly stood up and walked on two legs could never of happened, and some of the actions Manny did in Cabin Fever Greg has written about him could've been exaggerated in order to make him seem even more villainous to the readers than what he did in reality.

  • Confirmed. In a Metro interview published around the time of Hard Luck, Kinney wrote, "At first I was afraid kids wouldn't understand the irony and that Greg is a flawed, unreliable narrator."
  • Also confirmed in-universe at the end of The Deep End.

Nasty Pants is one of the Mingo Kids
Nasty Pants chases Greg and Rowley with a stick, just like some of the Mingo Kids. The reason we never see him around Greg's neighborhood anymore is because he now lives in the woods with the other Mingo Kids.

Diary of an Awesome Friendly Kid speculation
  • After Greg and Rowley stop drawing superheroes, they draw comics and come up with Zoo-Wee Mama!
    • We'll also get to see Creighton the Cretin in Rowley's style.
      • Now that the book is out, I can answer my WMGs. Semi-jossed with Zoo-Wee Mama! because while there are new strips, they're presented as being old in-universe and Greg and Rowley don't draw any more. Jossed with Creighton the Cretin, which isn't mentioned at all.
  • The book will be even more of a Random Events Plot than usual. The preview we got had a section header, so I can see the entire book being a series of random anecdotes divided by "the time Greg and I..." headers.
    • Confirmed, although not all of the headers are "the time Greg and I..."
  • The book will have a Call-Back to Rowley being on the student council in The Third Wheel.
    • Jossed. This book doesn't have any call-backs to books that aren't the original or The Meltdown (besides a minor one to Cabin Fever and The Ugly Truth).
  • Abigail will appear in the book.
  • The book will have numerous call-backs to The Ugly Truth. These include Cool Brian, Rowley's pimple, Jordan Jury's party, and the locket at the end.
    • Jossed, although the locket is referenced.
  • The Cheese will return.
    • Semi-confirmed. Although we don't see the Cheese itself, it is mentioned again and the story of Rowley eating it is re-told.
  • "Barmy" is the same grandfather who appeared in Rodrick Rules.
    • Jossed, as there's no evidence to confirm this.
  • The book will inspire a chain of other spin-offs, including more Rowley books and a Rodrick one.
    • Jeff Kinney did say that he wants to write more Rowley books, but no sign on a Rodrick one.
  • A scene from the book will involve Greg telling Rowley about the events of The Long Haul and/or The Getaway.
  • The book will solidify that Greg is an Unreliable Narrator.
    • Confirmed, unless Rowley is an intentionally, even less reliable narrator. Greg sounds like a far worse person in this book than in his own journals.

The movies are what actually happened.
Greg is an Unreliable Narrator, sure. But all his jackassery in the books isn't who he really is. Truth is, he's far nicer than he actually is, but he has so much self-loathing that he thinks he's an unrepentant jerk who lies, manipulates, and uses other people for his own selfish gain. Book!Greg is how he sees himself.

He also amplified the negative traits of his family members, especially his father, Rodrick, Manny, Patty, and Chirag, and also made it seem like Holly doesn't know he exists, nor does he include Angie in his journals because she was so minor in his life. All this reflects his frayed psyche caused by his aforementioned self-loathing.

Greg is the Mad Pantser
Notice how Greg was missing in the shot where the principal gets pantsed? Or that Rowley, of all people, was a target for the Mad Pantser? Oh, and the reason he stopped pantsing when chickenpox started going around was to throw suspicion off him.

In "Wrecking Ball," Meemaw's diamond ring will turn up
It was said in Hard Luck that Meemaw's ring was worth millions of dollars. The official synopsis for the upcoming Wrecking Ball says that the Heffleys get an unexpected inheritance. Given The Meltdown's callbacks to earlier books in the series, it seems likely that the next book will make a plot point of of a thread from an earlier book.
  • Jossed, it is not brought up.

Wrecking Ball speculation
  • Someone, most likely Frank or Rodrick, will get injured.
    • Greg gets hurt in a flashback, so semi-confirmed.
  • If the construction goes too wrong, Greg will find another place to stay for a while, such as Rowley's house.
  • The war between the Lower and Upper Surrey Street kids will be mentioned again.
    • Jossed, although we do see some characters from The Meltdown appear.
  • The moving can either go two ways: either the house is miraculously fixed, or Greg moves to a different house on Surrey Street. Status Quo Is God and nothing very big will happen.
    • Yep, even though the house is in no fit condition to live in, they still don't move.
  • Greg and his family will attend open houses.
    • Confirmed! They do attend an open house to find one to buy.
  • Greg has a ridiculous fantasy of what he wants his improved room/house to look like.
  • Some sort of dangerous animal will threaten construction.
  • Gramma or Grandpa will appear in the book.

Where will the Heffleys go after their house was destroyed at the end of Wrecking Ball?
The Heffleys will either move into the house Manny built or Rodrick’s van.
  • The whole thing might get hit with Negative Continuity.
  • The beginning of The Deep End reveals that they moved into Gramma's basement.

Loded Diper is a joke band created to mock Metal stereotypes
Based on what little we know, they are walking Metal stereotypes, complete with Basement-Dweller vibes and songs that are nothing but Insane Noise and Screaming (movies not withstanding). And besides, who would unironically join a serious band named "Loded Diper?"

The series will deal with more mature topics in later books.
Mainly stuff some children Greg’s age can still relate to. (Feel free to add some of your own.)
  • Rowley will come out as transgender, and change her name to something really ridiculous, like Cinderella. Greg will initially think his friend has gone insane, but after Rowley’s mother explains the concept of being Transgender to him, Greg will decide to cash in on it by making himself a girl too. (Bonus points if a girl Greg has a crush on at school also comes out as a trans boy, much to Greg’s frustration.)
  • Frank will develop diabetes from his sugar addiction. Bonus points if he later dies of a heart attack.
  • Frank and Susan will get into a more nasty fight than usual, climaxing with Frank slapping Susan in the face in front of the kids, leading to a divorce. Bonus points if Susan starts to date one of Greg’s teachers, much to his embarrassment.
  • Rodrick and his friends will get addicted to drugs, which may lead to his arrest.
  • The topic of school shootings will come up. Even if one doesn’t happen at Greg’s school, maybe he’ll see one on the news and become paranoid.
  • Rowley getting hit with a dose of reality in the Third Rowley book and realising that his Power of Friendship stuff causes him to be seen as childish.
    • Jossed, still the same naïve Rowley we know.
  • Depression, bonus points if it's Greg or Rodrick.

The final book will be a Distant Sequel.
It will be set ten or twenty years after the events of the original series, and will probably have Greg digging up his old journals and deciding to write a new one detailing his adult life, similar to Diary of a Wimpy Kid: 25 Years Later.

The pig will return.
And he’ll have a legion of intelligent bipedal clothes-wearing pigs that he’s taught his skills to.

Rowley is slightly special needs.
  • As a kid I assumed Rowley was how he was due to Greg telling the story. Maybe Rowley isn't as mature and his parents protective, but Greg is bullshitting stuff like Rowley hanging out with literal 6 year Olds. But then at work a few months ago I saw a book written from Rowley's pov. He mentions his mom bathes/helps him still. And it suddenly explains a lot that Rowley is a little behind on things nd his parents being how they are (I think they are implied to be older too).
    • This troper thinks that it’s just the way the Jeffersons raise Rowley, being overprotective.

Future Awesome Friendly books will finally give Rowley a dose of reality.

The later books are less down-to-earth than earlier ones because Greg's actual life became better.
The exaggerations started when Greg ran out of real things to write about. As the time progressed, Susan became less controlling and didn't meddle in his life much, Manny outgrew most of his quirks, Rodrick mostly left him alone, etc. But as his life got less shitty, at the same time it became significantly less interesting to write about. So, either because he still hoped to sell his journals or because he liked writing them just so much, he started to fill the duller episodes with imaginary adventures. Also, since his family members no longer committed actions as remarkable as in the first journals, he started to make them up himself, based on his family members' personalities as he remembers them. Obviously enough, he mostly remembers their most distinctive traits - thus, Flanderization occurs.

Rowley is smarter than we think.
In his third book Spooky Stories, the characters in the story Ghost Friend as a similar dynamic to Rowley and Greg. Does This Remind You of Anything? comes into play when you realise that this implies that Rowley is secretly aware of Greg’s treatment of him, and may be exaggerating Greg’s jerkassery in Awesome Friendly Kid to make him look more awesome and friendly.

The series will eventually have a crossover book with Dork Diaries, and it'll be one big allegory for their real life Fandom Rivalry
Whatever the main plot ends up being, the general concept would be that Nikki and Greg end up meeting each other while in a predicament, and they decide the best way to fix their problem would be to work together to reach a common goal. Everything that arises between them in the process draws parallels to a difference between the style of both series's. They eventually get along despite this, and ultimately become true friends with An Aesop about how friends can come in the most unlikely places if you focus on your similarities instead of your differences.

The cover of the book will show Greg and Nikki drawn on 2 separate paper scraps in their respective styles, giving each other a Disapproving Look. The back cover will do the same, but with Greg and Nikki happily reaching out of the edges of their paper scrap to hi-five each other. The title will be a fusion of both series's titles and fonts. Possibly "Dork Diary of a Wimpy Kid: Tales of a Not-so-overdue Crossover".

As for the actual book pages, they will appear as though someone tore pages out of Greg's and Nikki's diaries in large chunks and taped them into a generic empty diary in chronological order. This will cause the story's POV to swap between Nikki and Greg at regular intervals, possibly every in-universe day. And yes, this does mean we get to see Nikki drawn in Greg's style, and vice-versa.

The final book in the series will be a Distant Finale, similar to the finale of Arthur.
It will show what became of Greg and everyone else as they grew up, and the final page will be of a now-adult Greg writing the first book, showing all the books were an autobiography about his middle school years.

There will eventually be a book all about Greg ending up in outer space somehow.
It seems like no series can become a Long Runner without eventually having an installment that takes the story to space. The Wimpy Kid series is on it's way towards being one, so why not? A few possible ways this could happen:
  • Greg takes a trip (either with his family or on a school field trip) to a NASA launch station for fun/educational purposes. He gets lost and ends up in a rocket that's set to launch. The crew doesn't find him until they're already in orbit, and Greg must accustom himself to his new environment until they can get him back to Earth safely.
  • A downplayed, but more realistic scenario: After learning a few things about astronauts, Greg gets it into his head that he can become rich and famous as one. He signs up for a summer camp centered around teaching/training young teens for that career path using ultra-realistic simulations.
  • An even more realistic scenario: After learning a few things about astronauts, Greg gets it into his head that he can become rich and famous as one. The rest of the book details Greg and Rowleys attempts at schemes and plans that would "prepare" them to be sent on space missions the second they're old enough for it.note 

The movies are actually heavily modified versions of Greg's diaries that Greg rewrote as an adult
In the future, when Greg becomes rich and famous, he decides to get his diaries published for everyone - but there's a problem. When Greg re read his diary he realized how extremely unlikeable he is and he doesn't want people to read his books and see him as a huge loser and selfish jerk who can't a date during his youth. So what does he do? He modifies and edits and rewrites his "diaries" to make himself look good while making other people look bad. He heavily changed names to make sure they don't sue him and exaggerates the worst traits out of people such as Patty to make himself seem sympathetic. He also created Relationship Upgrade to Holly to show that he was always The Casanova (and later married as an adult) but also gave an Adaptational Jerkass to Heather so Holly doesn't find out he had a crush on her sister and get mad over it. He also gave an Adaptational Nice Guy to his entire family due to either him eventually coming to good terms with all of them and not wanting the diaries to break his relationship with them again or he doesn't want to be seen as The Woobie who's boastful about how rich he is as an excuse with coping with his childhood issues.

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