Skyline Tavern

A blog of tabletop roleplaying game storytelling, character development, and world-building

Halfling rogue sneaking

Making of a Halfling Thief Rogue

Mechanically, there are few more classic and optimized character player options than the halfling thief rogue. In this post, we’ll walk through the backstory of Ashley Walnut, a young halfling from Masonsville, and how she became an adventurer.

A privileged childhood

The Walnut Family

The nuclear family

Little Ashley Walnut was always taught how fortunate she was. She had two loving parents, her mother and father, and a baby brother who copied her every move. They weren’t nobility, but the happy halfling family enjoyed a comfortable living. Mr. and Mrs. Walnut owned a shop at the main square of Masonsville selling medicinal advice, herbs and concoctions to locals and travellers alike. They had considered enrolling their children in one of the city’s private schools. However, when Mrs. Walnut asked her then three year old, Ashley responded innocently with “why not that one?”, pointing at the school right across the street. So Ashley and her brother, Samson, attended the local public community school with children across the wide political and economic spectrum.

Every year before the winter solstice festival, Ashley’s father would load up the family in their horse drawn station wagon for their annual ski trip. Most of Ashley’s friends couldn’t afford skis. She was so lucky. Her father would make sure, every year, they stop off in the lower east side of Masonsville to put an hour or two of volunteer work in at the soup kitchen. He wanted them to get exposure to those ”less fortunate”. Mr Walnut would sometimes threaten his children, that if they ever messed up they would end up on the street, begging for food and Dawnfather knows what else, just like these people eating at the soup kitchen. The smell of the place was cause enough for the children to heed their father’s warning. Samson would get out of the volunteer work more often than not, using his motion sickness as an excuse.

Leaving the inner city and her school friends behind her, Ashley’s family would join their affluent friends in the alpine vacation homes. Everyone would show off their new skis, coats, flashy gloves and boot warmers. Ashley would happily put on her well worn gear from last season, squishing her toes in her boots. Even though she was growing, she kept a pair of racing boots for three years because they were a gift from her grandfather. She would smile to herself as she pulled the tongue up, remembering his round face and bald head fondly. Grandfather had loved her so much, and she missed him.

Ashley and Samson’s parents had many friends, who subsequently had children near their age. They weren’t the oldest, but they were always the best skiiers of the kids’ crew. Ashley was eager to be first on the mountain and last to finish, every day. The other kids preferred meticulously putting their outfits together in the morning, heading in early for lunch and hot cocoa, and hanging out in the steam pool in the afternoon. Even though they didn’t have much in common, Ashley loved spending time with these families, playing with kids her age. On one of these vacations, Ashley gave up a chance to ride on an airship in favour checking out the tea party exhibit her friend was excited about. However, this decision is one Ashley continued to regret all the way into adulthood.

Trouble with friends

Ashley always had trouble making good friends. Every time she’d meet a friend she really liked, something would happen. They would move away, their parents would separate, they’d drop out of school, they’d leave the sport’s team. It was always a crappy scenario for her friend, and Ashley never had an excuse to feel sorry for herself. These unfortunate situations would be convenient reminders for “how lucky” she was to have the life she had. But it never helped fill the gaping hole she’d have inside her. The painful feeling of loneliness and guilt all wrapped up as one.

Many of Ashley’s friends at school were in the “cool” group. But her favourite friends were always the less popular kids. One year, she made good friends with a nerdy student a year younger than her. Ashley was always impressed with the girl’s positive attitude and willingness to try anything, she was especially excited for her to join her on some of her adventures on the playground searching for ‘buried treasure’. During recess one day, Ashley went to say hi to her new friend. But the new friend was upset for some reason. She flung herself on to the highest horizontal bar, swung, and launched her feet deliberately into Ashley’s stomach. “That’s for being a horrible friend!” she’d shouted, and ran off before Ashley could even get a word in. This episode motivated Ashley to improve her fast-twitch muscles and reflexes. To this day, she still doesn’t know what she did to upset this girl.

In Ashley’s final year of grade school, the last year before she’d have to choose a discipline to study in career preparation, one of the teachers was taking the senior students on a school ski trip. Ashley was extremely excited, to finally ski with her school school friends. But her teacher, the elderly choir instructor, had a bad experience skiing with students one time. She forbade Ashley, and any of her students, to attend the ski trip. So, impulsively, Ashley’s mother took her and Samson out of school for that week and they went on their own family ski trip instead.

Raucous teen years

In this world, secondary school is where you start preparing for the career that will guide the rest of your life. Most of the public school students don’t make it to secondary school, as they need to begin work as soon as possible to help their families make a living. These teens usually take on an unskilled labour job, find a noble to serve, or if they’re lucky they can apprentice with a tradesperson.

For Ashley, there was never a question she would go to secondary school. Her grandfather had immigrated to the country when he was a young boy, and worked himself to the bone so his brother, children and grandchildren would get the best opportunities as possible. He knew what a hard life entailed, one riddled with racism, violence, and homelessness. He never wanted his own flesh and blood to have to endure that ever again. His success as a money lender outside the crown had allowed him to accrue a small fortune, some of which he delegated to his four grandchildren. Even if Ashley’s parents could not afford the schooling themselves, this gift from their grandfather would have enabled Ashley and Samson some choice in their schooling.

Of higher education and choosing a professional path

For secondary school, you had a choice between: the arcane arts, health studies, applied sciences, or commerce.

In second year, the arts students would branch off into two schools of study. The College of Bards, and the School of Wizardry, where they’d continue to hone and refine their skills. Bardom typically capstoned at year 3, when graduates would enter the real world to continue their lifelong studies of weaving magic through music and story. Wizards would typically take much longer to study. Specializing in one of the schools of magic, conjuration, evocation, abjuration, transmutation, divination, took a minimum of 4 years. They’d add another year for each other magic school studied. If they wanted to learn about enchantment, illusion, and necromancy, it would be another two years. And a very watchful eye on those who studied necromancy. Wizardry intrigued Ashley, but she thought it might be too much work.

The health studies students were mainly split between those who wanted to help others, and those who were deeply invested in their own physical health. First year studies were quite varied. Most students learned the basic differences between divine and natural healing, then memorized the names of different gods, healers, medicinal herbs and salves. Many health students also took active courses too, where they’d learn the theory behind hand-to-hand combat, archery, polearms, dueling, or wrestling. Whether a student continued down the physical education or the health practitioner path, they’d move more and more from the theoretical to the practical an average of 4 years.

Ashley enjoyed sports and exercise, but her parents had both studied health, and she had no interest in following in their footsteps. She loved the idea the arcane arts, history and religion, storytelling and music. But “those are nice hobbies, dear” her mother had insisted. Ashley stereotyped commerce as the track to go down for the future politicians and guildmasters, and the thought of affiliating herself with that lot made her feel ill. So that left applied sciences. Taking the inventions and instructions of people much smarter than her, and figuring out a way to apply these teachings to everyday use.

Moody halfling leaning against a wall
Ashley at the school pub

The applied sciences

Not the most flashy, or story-worthy, but the most practical, she thought. Four years of study, a little mix of classroom and practical, in and out. Then you were done with school and ready to make money. Plus the hiring rate for this program was about 90%, the highest of all four, regardless of what secondary school you went to. All she had to do was survive.

Secondary school turned out to be a pinnacle point in Ashley’s life. She finally started finding people who shared her interests and passions. She was living in the country, out of her parent’s home for the first time, and enjoying every minute of it. Her mornings were full of exercise, her afternoons chalk full of study and workshops, and her evenings centralized on a different tavern for each night of the week. She was able to pick up odd-jobs, fixing things and tweaking little contraptions, to pay for her expensive drinking habit.

It was in the tavern, not the classroom she learned to hit the bullseye with her throwing knives. The bar not the lab she figured out lock-picking for the first time. And those late nights having to sneak back into the locked dormitory rooms would later come in way more handy than all the calculations and theory she memorized during the four years of school.

As graduation approached, she was sad to be done. The friends she made here would be lifelong. The parties and shenanigans would be forever etched in her memory as the best days of her young life. But, every chapter ends, and her story was far from over.

Adulthood and the real world

Secondary school behind her, and the safe bubble of academia no longer there to protect her from the cruelty of the world, Ashley decided she wasn’t ready for her first guild job yet. She wanted to travel, to see new things and meet new people. She wanted to spend a year climbing and skiing the highest mountains across the continent, and made a grand plan with her best friend from secondary school to do so. It was all mapped out. She had saved from all the paid internships she had done in between semesters. She had crafted a new pair of skis she specifically made for this adventure.

Mountainous landscape
Aspen peaks and grassy fields

But her best friend bailed last minute on the trip. She said it was too expensive, then ended up going on a more expensive but shorter trip to the fancy coastal cities with another friend. Ashley had been invited to come too, but knew it wouldn’t be the same as her dream trip. Instead, she joined two of her former roomates and camped out in a small trailer for a season to ski and explore a local ridgeline. This ended up working out well. She was able to refine her ski design and even sell a few pairs to pay for groceries. And it was nice to be close to home when she got the letter that her mother had fallen ill.

A knife to the heart

With life-changing news, Ashley packed her things, bade the trailer park fairwell, and went back home for the first time since graduating grade school. Her brother had just started his secondary education and her father was still working long hours in the shop. Being back home brought great relief to her family. She wasn’t very good with medicine or bed care, but did what she could and learned from her father and her aunts. They eventually decided it would make better sense for her to spend more time at work and to help pay for the expensive treatments, and for her father to scale back his hours and manage the house. So she went on the job search.

Even though her school had a female to male ratio of about 50%, when you just looked at applied science it went down to 35% female. Then going out into the real world it was more like 25% women. Once you split into the different artificers and rogue types, Ashley was left with an abysmal gender ratio, with only about 10% rogues in her field being female. At least there were more halfling rogues than dwarves or genasi? But still way less than the common taller, stronger humans and elves. Needless to say, Ashley submitted application after application and had countless interviews with old white-haired men who towered over her.

Maybe she wasn’t as smart as she thought she was. These men certainly didn’t think so. Maybe she should have drank less in college and spent more time at the library. Perhaps she wasn’t cut out for this kind of work at all. The job hunt seemed to go on forever. Even though she had only properly been at it for 4 months. The confidence gained during secondary school quickly evaporating.

Tricks of the trade

Eventually, an old classmate got her name to the top of the pile with their employee referral program. Ashley would start her career at Chicken Burger Associates, 12 months after graduating and gallivanting in the backcountry.

It wasn’t exactly what she’d had in mind when she started applied sciences, but she was learning a lot at least. The office was downtown Masonsville, a short walk from her parent’s house. It was a square stone building, grey, well maintained. Clean. She had her own desk with her name chiselled into it, but she rarely sat there. The majority of her time would be spent in the field. Accompanying all the different sub-contractors on various projects. The company had started out in food services manufacturing, but had since grown expertise in many different sub-industries of applied science. Sometimes she’d be in the quarry, taking notes and doing the odd hardness test. Other times she’d help guide larger machinery through cave systems, the dainty halfling with moonlit rapier out front, guiding the burly half-orc and goliath operators to the test locations.

Halfling rogue sneaking
Ashley on a stealth job

People aren’t like wine, they don’t improve with age

She worked for a few years, always jumping at an opportunity to learn new things. A few of her colleagues became good friends and passed on wise words of advice on how to be successful. For example, they taught her what lies to tell contractors if they’re being inappropriate, like “if he makes a move on you, just tell him you have a boyfriend” or “don’t make eye contact, he’ll eventually start ignoring you”.

Ashley had heard stories before, but it was completely different when it was you in those stories. Most of it was ‘harmless’, but sometimes it wasn’t. They seldom listened to “no”. “No” seemed to mean “yes, just work for it” to many of them; and as she gained rank in the company she requested more and more office work to avoid these situations. But then it started to happen in the office as well. No one ever paid much attention to her in grade school, boys or girls, and it was very much the case in secondary school too. But when you’re that cute little halfling and there’s about 5 times the amount of men to women, you tend to stick out in all the wrong ways.

“Just ignore it,” her friends, who many were in similar situations, advised. “And certainly don’t complain about him.” if it was someone ‘important’, or the son of someone important. “Just don’t drink too much when you’re out with them.” or “he’s nice, though, isn’t he?”. She watched the three senior women in the company, how did they deal with this?

One of them was basically a mute. She was a tall half-elf, strong and lean, confidently striding around the office. Her blond hair was always neatly pulled back in a perfect bun, kept in place with a decorated pin. Another was a dark skinned human, with rich auburn hair that flowed down to her waist. She let it all out. She was proud of who she was. Or so Ashley thought. As she watched this woman more and more over the years, she noticed the face twitch when she’d make a self-deprecating joke, the pain in her eyes when she said everything was fine at home. The way she would slump in a chair and slur how the world had gone to shit years ago, if you caught her too many drinks in and with the bosses not around. And the third woman, who was head of HR, and who’s father had started the company way back when. She didn’t “see race” or gender, most conveniently, and would tout how positive the company’s inclusivity performance indicators were all the time.

The way the men would talk about these women and the others in the office was also off-putting, to say the least. She was too loud. Too quiet. Too good at her job, she must be flirting with the operators every day. So dramatic. Doesn’t take things seriously. Takes things way too seriously.

You couldn’t win. And if you weren’t what was in their head as feminine, that was even worse. One of Ashley’s work friends was forced to hide her sexuality because it wasn’t safe for the company to know the real her.

So Ashley got better at hiding her emotions, at keeping her voice even, at doing her tasks and putting in her time. She only asked questions when they had to do with the job at hand. She only complained after everyone else in the room had too, and even then would add “but it’s fine.” Was it really fine?

The best lesson of life is learning that it’s finite

Then her mom stopped responding to her treatment. She hadn’t been able to get out bed, let alone the house for a month now. Her father, her brother, her aunts, everyone was talking about how the next cleric would help or another salve she could take. One night, Ashley sat fading in and out of sleep in the chair next to her mother.

“You always had trouble with friends…” her mother whispered. Ashley opened her eyes and saw her mother gazing slightly drug-induced at her, her pale face gaunt in the moonlight, her head smooth except for a couple small tufts of flame-red hair. “But now you have good ones, and that makes me happy.”

It only lasted a few minutes, but Ashley would always cherish the conversation with her hero.

“You know, death is just a part of life.” Mrs. Walnut’s eyes closed. “One day soon, I’ll die. But you all need to keep on living. I know it’s hard for you, but you’ll be okay. You’ll all be okay.”

It was the last real conversation they had. After that night, Mrs. Walnut would sleep a lot. Eating only what they forced her to. Her answers were short. She had no questions.

On a beautiful summer day, just before her 22nd birthday, Ashley finished dinner with her father and brother, then went to say goodbye to her mother. “I’ll see you tomorrow.” but Mrs. Walnut wouldn’t be waking the next morning.

This was the final straw for Ashley. She took it as a sign from the universe. She quit her job, paid her last week’s rent, and set out with her travel pack for a new adventure.