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Characters / Dillydale-Less

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Note: This page only showcases original characters from the series. For characters from the cartoon it's based on, see The Mr. Men Show.

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    One Calamitous Date 

Mr. Toil

Miss Calamity's co-worker and rival, a nerdy and highly intelligent accountant who started off as a bully to her, before eventually mellowing out and becoming her friend.

Mr. Chair

Miss Calamity's chauvinistic, aggressive, tyrannical, and lazy (former) manager. Although later artworks show that he has changed for the better, in One Calamitous Date, he's a massive Jerkass and the Big Bad. At end of the story, he was revealed to be Mr. Toil's long-lost father.

  • 0% Approval Rating: NOBODY at Miss Calamity's workplace likes Mr. Chair. Even Mr. Toil, who initially sucked up to him, admits to having a disdain for him, and flat out turns against him towards the end of the story. He also has earned contempt outside of work due to his horrible personality in general.
  • Abhorrent Admirer: He is attracted to Miss Calamity, despite the fact that she can’t stand him.
  • Bad Boss
  • Big Eater: Downplayed. While he's never really seen eating enormous amounts of food at once, he's a Fat Bastard who indulges in junk food and gets extremely impatient when his food takes a long time at restaurants.
  • Big Ol' Unibrow: A combination of Type I and Type II.
  • Berserk Button: Getting his coffee wrong.
  • Big Bad: Of “One Calamitous Date”.
  • Break the Haughty
  • Brooklyn Rage
  • Butt-Monkey: Due to his jerkassery, he’s the unluckiest one in the cast.
  • Deadpan Snarker
  • Dirty Coward: When confronted by a sea monster, Mr. Chair pushes Miss Calamity and a random fisherman into his path and takes off.
  • Dirty Old Man: He’s at least middle-aged, yet fawns over women much younger than him.
  • Cool Old Guy: After his Heel–Face Turn and Character Development, especially towards his grandchildren.
  • Even Evil Has Standards: He was horrified when he believes he ran over Mr. Just. He's also disgusted by domestic abuse.
  • Fat Bastard
  • Fat Idiot
  • Formerly Fit: Used to be a skinny guy, but is now obese.
  • For the Evulz: His petty torment of Miss Type (amongst other employees) seems to be based around this.
  • Guttural Growler: His voice has been mentioned to sound very deep and raspy.
  • Hair-Trigger Temper: He has some rather frightening anger issues.
  • Hates Everyone Equally: He's a miserable person who doesn't seem to get along with anyone. At least this was until character development when he started to show love to his family, especially his grandchildren.
  • Hate Sink: Starts as this initially. Subverted after he goes through a Heel–Face Turn.
  • Hidden Depths: Has an interest in movies and dogs.
  • Huge Guy, Tiny Girl: The huge guy to Miss Type’s tiny girl.
  • Hypocrite: He makes fun of an employee's weight, despite having a large gut, something that he put upon himself anyway from a horrible diet. He also calls Miss Type “ugly” despite being old, balding, and conventionally unattractive.
  • I Was Quite a Looker: Was thin and had a full head of hair when he was younger.
  • Jabba Table Manners: He burps loudly during his dinner with Miss Calamity, and then moments later gets drunk off wine.
  • Jerkass: In One Calamitous Date, big time.
  • Jerkass Realization: He eventually started to realize how horrible he has been all these years, and attempts to redeem himself.
  • Jerk with a Heart of Gold: Finally started to mellow out eventually, and seems to genuinely love his grandchildren.
  • Mean Boss
  • Must Have Caffeine: Without caffeine in his system, he can throw a rather nasty tantrum if you do so much as get him the wrong coffee.
  • My God, What Have I Done?: Is visibly horrified when he runs over Mr. Just.
  • Pet the Dog: A quite literal example in that he has a soft spot for dogs. He even eventually gives his grandchildren a puppy for Christmas, to try to be on good terms with his family. There's also a very minor moment in the "One Calamitous Date" story where he gets Miss Calamity something to eat for lunch, and even apologizes for making her drop her phone in the ocean.
  • Pointy-Haired Boss: Incompetently lazy, and compared to Mr. Toil and Miss Type, he's not much in the brains department.
  • Politically Incorrect Villain: He has a shallow attitude towards women, and uses "retard" as an insult.
  • Psychopathic Manchild: He throws temper tantrums like a three-year-old when he doesn’t get his way and childishly complains when he’s bored, to the point where he makes pre-development Mr. Toil look mature by comparison.
  • Sensitive Guy and Manly Man: The manly man to Mr. Toil's sensitive guy.
  • Sir Swears-a-Lot: He swears the most out of the other characters.
  • The Slacker: Despite being, well, an office manager, he's barely even efficient in his job and mainly just forces his secretary to carry out his own work. Really, the only tasks he does himself is hiring, firing, and bossing around employees.
  • Trademark Favorite Food: Coffee and soda. He gets rather irritable if he's deprived of either of these.
  • Villainous Crush: On Miss Calamity.
  • Would Hit a Girl: He's a bully to Miss Type and at one point he poured (thankfully iced) coffee over her. Miss Calamity was scared that he would start hitting her or throwing things like staplers at her.
  • Why Did It Have to Be Snakes?: He's afraid of cats. And heights.

Little Miss Type

Mr. Chair's personal assistant, or used to be, whom he verbally abused, overworked, and underappreciated on a daily basis. In the story, she assists Miss Calamity in getting revenge on Mr. Chair, in retaliation for all his mistreatment towards her. When Mr. Chair got fired from his job and Mr. Toil became manager, she not only becomes the latter's secretary, but also falls in love with and eventually marries him.

Mr. Just/Officer Just

Little Miss Superior

Miss Calamity's other cubical neighbor, who is known to use her looks to get what she wants.

Little Miss Delicate

A co-worker of Miss Calamity. Very quiet and sensitive, she is often on the receiving end of insults from Mr. Chair.
  • Beta Bitch: She is usually alongside of Miss Superior assisting her, though she's too nice to really be a threat.
  • Fat Girl: Which results in her being a target for Mr. Chair.
  • Nice Girl: She genuinely doesn't hold any ill-feelings towards anyone. While she does do a few questionable things, like teaming up with Miss Superior in antagonizing Mr. Toil, or telling Miss Calamity that she didn't want to talk to her out of fear of being made fun of, she is usually very polite and non-malicious.
  • Shrinking Violet: Even moreso than Miss Type.

Mr. Dull

A male employee at Miss Calamity's workplace, who is a stereotype of your everyday office drone.

Mr. Optimistic

Another male co-worker of Miss Calamity, who is usually upbeat even while working his dreary job. He often tries (and fails) to make friends with the boss, unaware that Mr. Chair finds him annoying for his overly-happy attitude.

Little Miss Business

Mr. Toil's mother, and Mr. Chair's ex-wife.

  • Abusive Parents: Her attitude towards Mr. Toil is...unsettling to say the least.
  • Bad Boss: If the way she treats her assistant is anything to go by.
  • Bigger Bad: She was the reason why Mr. Toil was the way he was, and possibly one of the reasons why Mr. Chair is as bitter as he is.
  • Corrupt Corporate Executive
  • Hate Sink
  • Jerkass: She is a slimeball of a businesswoman who yells at her assistant, and doesn't care about her son at all. Unlike Mr. Toil and Mr. Chair, this is played completely straight, with no moments of kindness.
  • Jerk with a Heart of Jerk: You think she would learn from her wrongdoings and make amends with her son? You're completely wrong.
  • Married to the Job: A rather serious example, as she cared more about her job than her son and now ex-husband to the point of flat-out neglect.
  • Not So Different: As much as she denounces her association with Mr. Chair, the two have a lot of similarities to each other. Both of them run a company, have glasses-wearing, opposite-gendered secretaries whom they maltreat on a daily basis (formerly in Mr. Chair's case), have blue, elongated bodies, and are mean, cruel, and abusive people who abandoned their son, get angry over botched food requests, and park in handicap spots. Though the only difference is that Mr. Chair improved himself and became a better person, while Miss Business still remains a flat, static character with no redeeming qualities.
  • Trademark Favorite Food: Sushi, specifically spicy tuna rolls. She gets really upset when she gets the wrong sushi.
  • Walking Spoiler

Little Miss Endeavor, Mr. Moil, and Mr. Bookish

Mr. Toil and Miss Type's children, fraternal triplets whom they have at some point after the events of the story. Miss Endeaver is the oldest, Mr. Moil is the middle child, while Mr. Bookish is the youngest.

Mr. Submissive

Miss Business's assistant.


    Golden Sunshine 

Mr. Destiny

A famous movie star who appears to be a friendly guy to the public, but is actually a spoiled, bad-tempered, narcissistic prima donna. He's had a burning hatred towards Mr. Happy ever since he "stole" the role he wanted in a movie, though this is unbeknownst to the optimistic Mr. Happy, who thinks the two are good friends.

Little Miss Rocker

Miss Sunshine's manager, who runs the flower store she works at.

  • Deadpan Snarker
  • Fallen Princess: Originally the lead guitarist to a metal band, until she was fed up with celebrity life and left, downgrading herself to a flower store manager. She doesn't seem to mind living a normal life, even criticizing celebrity life, though does miss music sometimes.
  • Jerk with a Heart of Gold
  • Mean Boss: Downplayed. She comes off as a stern and strict manager who's a Deadpan Snarker, but does show at least consideration for people, even towards Miss Sunshine.

Little Miss Bubbly

Miss Sunshine's best friend.

Mr. Chill

Mr. Brash

Mr. Happy's best friend, a successful reality show host.

Little Miss Diva

A famous pop star, who Mr. Happy used to date.

    Making Magic 

Mr. Mojo

Miss Magic's manager, a greedy and arrogant magician who owns a magic show. He's a Bad Boss to Miss Magic, pretty much treating her like a prop for his shows, and constantly looking down on her for having trouble with her magic skills.

    Rude Service 

Chef Gourmandise

The owner of the restaurant Mr. Rude works at, and Mr. Rude's boss. A bit on the ill-tempered side and bent on giving his restaurant a good name, he is demanding to his employees, and is especially harsh with Mr. Rude, whom he can't stand. On the other hand, he is benevolent to costumers, wanting to give them the best experience possible and provide a good reputation for his establishment.

  • Big Eater: He loves food, and eats a lot, resulting in his large body shape.
  • Bilingual Bonus: His name is French for "gluttony".
  • Chubby Chef: He's a large guy, due to his love of food.
  • French Jerk: Downplayed. He's not a jerk in general, just to Mr. Rude.
  • Supreme Chef: He takes his work very seriously.

Mr. Savour

A renown food critic/former TV chef from England. He tends to be rather aloof and bitter towards people, though if you manage to impress him enough with your cooking, he can turn out to be a decent guy. One of his major pet peeves is restaurants that lack cleanliness, and is immediate to chastise any restaurant that has the slightest hint of being unsanitary.

    Tickle Me Clueless 

Mr. Omocha

Mr. Tickle's boss, a businessman and CEO of the Japanese toy company that Mr. Tickle works at. Dedicated to his work, he is a good-natured, honorable man who is well-liked among the workplace he runs. Despite being impatient at times, he is fair to employees. He is also on good terms with Mr. Tickle and sees him as an employee with potential (though he does find his tickling annoying).

    Feeling Nervous First Time On The Job 

Mr. Challenge

Mr. Nervous's sidekick in his job. Despite his youth and size, he's brave, energetic, and always up for adventure. He's always the one to help Mr. Nervous overcome his fears so that he can succeed in his job of filming ghosts.


     Bumping Forward 

Little Miss Bell

Miss Whoops' boss, a woman with a thick Southern accent who runs the diner that Miss Whoops works at. Since the diner doesn't really get much business, she doesn't make much of a big deal over Miss Whoops' accidents, and keeps her around since she is understanding of the clumsiness that she can't help. She does try to help Miss Whoops improve at her job.


Example of: