Dorothy Whittle Background (Patreon)

Basic Facts

Dorothy Whittle is the Guild Mistress of the Cransmere Adventurer's Guild. She is twenty-six years old, has been in charge for three years, and worked as an Assistant Guild Mistress for five years before that. She comes from the aptly named Whittle Farm to the south of Dawnstead located in southwest Arrark. She lived near a smaller fishing village, Priddlesby, which was only a short boat ride to Dawnstead.

Family

Dorothy is the only child of a pair of farmers.

Humphry Whittle, her father, is a scrawny, bookish man who was never cut out to be a farmer but had no choice but to inherit the farm. It was him who instilled in Dorothy's love of reading into her and taught her all sorts of things about the world.

Sarah Whittle, her mother, counters her father in many ways. She's bigger and taller, more fit, very outspoken. She wears the pants and it's not even close. Dorothy inherits almost nothing from her, but perhaps as Dorothy's character development continues she might develop a fiercer streak from time to time.

Early Life

Especially when compared to the other members of the cast in Coye's eventual harem save for Suzette, Dorothy had the most normal childhood. There were no epic circumstances which led to her birth, she was merely the product of two people who loved each other very much. Her family were farmers, and Dorothy spent her earliest years learning how to take care of crops, attending the livestock, and performing all sorts of little chores. Being a meek and quiet girl, Dorothy never complained about her life and was happy to be with her family. Her father taught her how to read and write, while her mother led her around the farm.

Dorothy loved taking the boat to Dawnstead more than anything else. Her farm and the nearby village were both shoddy, and the beautiful streets and marble statues of the city of light amazed her. She wished to live in such a city one day, but even as a child she realized she'd likely be stuck on the farm her whole life. Her favorite place in Dawnstead was the library, where every visit she borrowed as many books as she could carry. Dorothy would resort to stuffing her shirt full of books and just to take even more with her, and the librarians there loved her and allowed this to happen.

Even then, her favorite topic to learn about was monsters. She liked scary stories that got into details about them, grisly first-hand accounts from adventurers, heavily illustrated bestiaries and the like. Her parents accepted this weirdness and encouraged it, so long as she diversified and borrowed books on other topics, too. They knew how smart their daughter was and they were already talking behind her back about how it would be a waste for her to stay with them for her entire life.

Rough Times and Solution

Times grew harder than they already were when Dorothy was eight years old. There was an earthquake to the east which disturbs the local ecology and sent the monsters that live in the area into a frenzy. They became much more bold and attacked both the village and Whittle Farm at frequent intervals. They didn't have enough money to hire adventurers, so there was little they could do besides fight them off themselves.

It was rough, her parents rarely got any sleep because they had to keep an eye out throughout the night. Food became scarce, as did gold. The entire time, Dorothy kept trying to convince her family to let her help. They wouldn't hear it, as she was just a child. One day, she had her chance to step up and prove herself.

Both her mother and father were injured in the latest attack. Not lethally, but enough to put them out of commission. They urged Dorothy to run to the village explain the situation, but Dorothy knew if she did that it was likely they would die. Dorothy performed first aid on her parents herself, using knowledge she'd gained from books. This alone was impressive, but it was everything Dorothy did next which truly illustrated the depths of her creativity and knowledge.

Dorothy knew the monsters of the local area like the back of her hand. She was fascinated by them, and had read countless books about them. Such knowledge came coupled with knowing how to kill them. She only had a few days to prepare for the next attack inevitably came, but Dorothy made the most of it and her parents watched in awe of what happened next.

Dorothy had the horses plow pitfalls, covering them up with net and hay. She sprinkled them with bait. Following Dorothy's commands, her parents helped her sharpen stakes to put at the bottoms of the pits. They made snares, sound traps for monsters sensitive to sound, bombs which would make flashing lights, and so much more. After certain point her parents just shut up and did whatever she told them to do. They couldn't believe the spirit of their meek and timid daughter when she put her heart into something.

The time the monsters appeared, they were ready. Dorothy orchestrated a flawless defense, even though she was scared out of her mind. She gave commands to her parents, who were able to walk again but still felt weak, and for every species of monster that showed up, Dorothy seemingly had an answer. Not a single one broke through the perimeter, and many of them died trying. Dorothy's parents were stunned. They knew their daughter was special, but this made them believe she was brilliant.

Things Get Better

After their recovery, Dorothy's parents brought her to Priddlesby so she could share all the different tips and tricks she'd developed. It wasn't long after that the monster threat started dying down, in no small part to Dorothy's contributions. The little fishing village was suddenly taken with her, and the shy little girl had no idea how to handle all that sudden popularity. They gave her treats whenever she was in town(she was even chubbier as a child than she is now), or books, and some people even started stopping by the farm to help out with random chores so that Dorothy could focus more on her reading. The farm started to thrive because of this, and they even expanded the land. It was still small, but their standard of living went straight into middle class.

Dorothy didn't know it, but plans were being made for her future. One of the townspeople said Dorothy should work for the Association when she gets older, as they need people who know monsters like the back of their hand like she does and they pay really good. The only problem was getting into their training program cost a lot of money- first for the enrollment exam and then for whatever path she takes.

Dorothy's parents love the idea, but it seemed too far-fetched of a dream for her. They would never make that much money, they thought. Of course, the village stepped in and everyone started saving bit by bit to put her through the Association Academy if she was interested in it. It was hard to accept such charity, but they did so for the good of their daughter.

When Dorothy turned thirteen, all of this was explained to her. There would be an entrance exam in Dawnstead later that year if she was interested. She was, but it took a lot of convincing to get the timid girl out of her shell. She was immensely grateful for what the town did for her, but they wouldn't hear anything about it. As long as she didn't forget them, that was good enough.

Dorothy spent several months studying every hour of the day before taking the exam at the Dawnstead Adventurer's Guild. It was an immensely hard exam, not typically for someone so young. They had to wait another month for the results, but when they got them back they were all surprised. She'd received high enough marks that she could enter the training course for any career path she desired. Naturally, this included the heavily sought after position of Guild Master, which was rarely offered. That was also the most expensive course, but she was pushed into accepting by everyone around her. She decided to go for it.

Association Academy

Dorothy packed up her things and was transported from Dawnstead to Imperalis where the Association Academy is located. She spent four years in school here, staying at the dorm and keeping to herself. She had few friends, still mostly preferring the company of books to others, especially with how expansive the academy's library was. Her coursework was crushingly difficult, no doubt meant to prepare students for the workload one could expect of the job they were training for. Things she studied included monsters, negotiation skills and tactics, sales, the code of conduct, employee management, adventurer management, resource allocation, and so on.

Her use in school were immensely stressful, but very fulfilling. Dorothy was not an honor student, but her grades were quite high and she was seen as a very solid and reliable pick to become a Guild Mistress in the future by her instructors and Association bigwigs like. When she graduated from the program, the next phase of her career was to serve as Assistant Guild Mistress for a minimum of three years, where she would either be assigned the next available post or wait until retirement of her superior.

Dorothy requested Dawnstead as her preferred post, wanting to remain close to home, but someone else was assigned there and she was stuck with Cransmere instead. She was given few months to return home and see her family and friends in the village before packing up. She started her new job while she was eighteen.

Years as Assistant Guild Mistress

Dorothy didn't like Cransmere the second she first arrived. Few did, but it's always creeped her out more than most. It was shoddy in a different way than the village of her youth, but one benefit it had was the wildly diverse array of monsters to study there. She worked under the Guild Master Beckett Eckerson, an older man in his late fifties who was friendly enough. He took her in as a mentor and she helped him run the place for five whole years.

During this time, Dorothy didn't make much of a splash. She did her job and she did it well, but she was never popular. Her awkward personality put off most people and her timidity made her have to rely on Beckett more often than not in order to make people take her seriously. He was supportive, telling her that it took him a long time to get used to having authority, too.

Time passed, nothing much happened other than clerical work and learning from her mentor. The creeping influence of the woods had an effect on her, drawing her to develop a snacking addiction that manifests whenever her stress is at its highest. Other than that, little changed.

Sudden Promotion

Change occurred when some of Mr. Eckerson's crimes came to light when Dorothy was twenty-three. It got out that he was sending adventurers on quests off the book, gathering items of personal interest. Some of these quests proved fatal to several adventurers, and he was stripped of his rank, his assets were seized, and he was taken in by the Association's enforcement squad.

Dorothy was briefly interrogated by them as well, but it was quickly determined she had absolutely nothing to do with her predecessor's illicit activities. This was in part due to her solid record at school, lack of corroborating evidence, and the testimony from employees and adventurers alike claiming she wasn't that sort of person. They made these claims in a somewhat derogatory way, like there's no way she'd be capable of that. Regardless, Dorothy was offered the job of Guild Mistress faster than she could prepare for.

Life as the Boss

The rest from here is fairly obvious, and we know a good deal of it from the main story. In the three years since taking the job, Dorothy has struggled to keep the place afloat. The Guild is profitable, but only barely avoiding scrutiny from the Association due to her talents. Her skills are often wasted doing work which other employees should be taking care of for her, and she can't afford to hire more help than she already has.

Tammy was hired half a year into Dorothy's first year as a Guild Mistress, and although Tammy isn't completely useless, she has the fantasy equivalent of autism and/or ADHD. The only reason Tammy is kept around is because her Lord father makes donations to the Guild just so that his useless daughter isn't laying around in her bedroom doing nothing. Tammy is the closest thing Dorothy has to a friend, but her irritation with the receptionist's antics prevents them from growing that close. In the future, that gap will lessen. Sadly, the amount of gold that Lord Rheingald donates to keep his daughter employed doesn't really make up for all the extra work Dorothy has to do because of her. At least it gives her a good relationship with one of the local lords, which in turn gives her juicy quests from time to time.

Her adventurers don't treat her very good, as well. Dorothy isn't the most personable and her offputting fascination with monsters has a habit of annoying some people. She talks too much for her own good, making her seem desperate and like she's trying to be overly friendly or fake.

Many days, all these problems are too much for her to bear. Dorothy struggles to keep going on as things are, the only thing getting her up in the morning is the memory of how much everyone back home sacrificed for her to be where she is today. She writes back home often and lies, telling them everything is alright when it's not. She also sends back a chunk of all the gold she makes, whatever is left after accounting for her RealMonster addiction and her binge eating habit.

The farm is doing well after all these years, if nothing else. Her gold has allowed her parents to start winding down and pay for full-time farmhands to manage the bulk of the work. Even so, her parents are just another one of Dorothy's stressors at the end of the day. They want grandchildren, someone who will take care of the farm when they're gone. It's brought up in nearly every letter they send her.

In this document I don't see the need to go over her relationship with Coye or how her future interactions in the story will go, as we've seen fair amount of that and her developmental happen throughout the story as opposed to a central arc devoted to her. I'm sure she'll get one, but it's irrelevant here.