Lily Wanderfoot

Lily Wanderfoot grew up in the countryside, but lost her parents and entire Halfling community in a tragic fire when she was very young. All she had left to remind her of her early childhood were her father’s brass compass, and Milo, her pet mouse. With no home left, she fled the countryside in search of the mysteries of city life. To survive the harsh conditions of living on the street in the city, she found it difficult to hold on to the values of honesty and respect that her parents had instilled in her and quickly learned to be independent, relying on her small size, nimbleness, and stealth. She also trained Milo to help her retrieve things or act as a lookout while she was relieving an individual of their unnecessary assets.

She eventually fell in with a group of older street kids who tricked her out of what little money she’d been able to scrape together. She was found and taken in by a local monastery shortly after. During her stay, the monks quickly recognized her penchant for staying hidden. This combined with her small size and shrewd intuition made her a prime candidate for being trained in the Way of Shadow.

The heads of these [Way of the Shadow] monasteries expect the unquestioning obedience of their students (PHB 78) and Shadonight was no exception. Although Lily hated being told what to do, and at this time was still wary of trusting anyone who claimed to be helping her after her experience with the street kids, she ultimately decided that the benefit of what she could learn from Shadonight and the other shadowmasters outweighed her aversion to taking orders.

Part of that training included developing her perception skills. While it did not take much effort for Lily to get a good read on a person or situation the shadowmasters noticed her tendency to overlook details or nuances. They knew that her level of distractibility was in part due to her young age but were nonetheless adamant that she hone her skills. Lily had little patience for studying or listening to lectures about the monastic traditions and values and was eager to “get to the exciting stuff.” The shadowmasters insisted that this part of her training was equally as important as her tactical training and required the same levels of perception and focus. Although Lily did improve those skills in her training her impulsiveness and desire for action usually win out when there is a choice between waiting and doing. This obviously is not helpful when it comes to reading or research, which is why she still seems to be unlucky in libraries.

Her training continued as she went through the dangerous fitness courses found in and outside the monastery. In the beginning she was often reprimanded for being caught unaware of a nuance of the course. However, the lessons of being aware of your surroundings and opening her mind to anticipate the unexpected were more quickly and firmly grasped through this training. After repeatedly being stopped, caught, or otherwise hindered while going through the course she eventually learned that her desire to jump into action must be tempered by a vigilance for protecting oneself. Like with the games of Chess or Go that she played with some of the older, less active shadowmasters, she learned how to utilize her natural intuition in various environments while also looking further to consider her next moves.

The shadowmasters eventually allowed Lily to shadow (pun only partially intended) them in some of their escapades. She’ll always remember one particular job she was allowed to tag along on. It was a night when the stars seemed to align for her--the night that she knew her training had come to fruition, the night she noticed something that no one else did. It was a foggy winter night. Two shadowmasters had been assigned to find and recover a medallion that had been stolen from a wealthy merchant. The merchant had come to the monastery to enlist the help of the skilled shadowmasters. Although she was less skilled than the two shadowmasters she was accompanying, her knowledge of the city streets helped her not only keep up but at times even allowed her to contribute by pointing out the best routes to take to follow the suspected thief while remaining unseen. The three were able to track the thief to an alley, where he seemed to be residing. The two shadowmasters were moving in to apprehend the thief when they felt their shirtbacks being tugged. The turned to see Lily, eyes wide, giving a determined shake of her head toward the thief. Both faces returned stern looks as they tried to silently communicate that they already saw what she was showing them. Annoyed at the interruption, they turned around began closing in on the thief. They were almost silent in their attack, the thief really never had a chance. Lily saw the thief struggle for just seconds before going limp.

On the way back to the monastery, they realized Lily was not behind them. Both were livid that she was again causing a delay in this job but knew that Shadonight’s reaction to their return without Lily, even with the thief in tow, would be unbearable. So they retraced their steps back looking for her but made it all the way back to the alley with no Lily in sight. They walked down the alley and finally saw a small figure rummaging through a pile of thief’s belongings. The shadowmaster who was not carrying the thief grabbed her by the collar. She struggled with him for a good minute, longer than the thief had lasted, but was eventually overpowered. The next thing she knew she was waking up inside the monastery to the visibly angry faces of the shadowmasters and the cool, stern face of Shadōnaito. The shadowmasters complained of Lily’s selfish and impulsive behavior, explaining that they had had to return to the alley only to find her trying to gain something for herself from the thief’s belongings. Shadonight held up his hand, silencing the two. He turned to Lily and gave her a look that she knew meant she was to explain herself. Feeling the anger rise within her, she wanted to yell out in her defence. However, she utilized her insight to read that this situation would be better played out with fewer emotions and fewer words. So, instead she reached into her pockets and began pulling out things she had taken from the thief’s pile of belongings; a brass chain, a bundle of string, a piece of soft fabric, a few copper coins, and...the medallion. The two shadowmasters looked at the medallion and then turned to each other in disbelief. Lily had been the first one to see the thief turn down the alley and she had also seen him stuff the medallion into the pile. That’s what she had tried to communicate to the others before they apprehended the thief. Her keen perception had completed the job.

Throughout her time at the monastery, there were many occasions when the shadowmasters were displeased with her restlessness--although their disciplined training prevented them from explicitly expressing these feelings. But Shadonight, stern and aloof as he was, seemed to have a higher level of patience for Lily and always pressed for her continued training. Perhaps it was because he recognized her potential to become an invaluable addition to their league of shadowmasters. Or perhaps it was because he saw something in her that reminded him of himself a great many years ago. Whatever the reason, Lily remained under the care and training of the monastery until her 17th birthday.

Lily still believes the inherent value of people and wants to be helpful to them when able, but can be wary of letting others help her. She has learned much and come to appreciate the monks who took her in, but she also fears getting too emotionally attached to anyone after the great losses she has suffered. Anyone except a Dragonborn Paladin she ran into.

Stats & Specifics
Background - Urchin

You grew up on the streets alone, orphaned, and poor. You had no one to watch over you or to provide for you, so you learned to provide for yourself. You fought fiercely over food and kept a constant watch out for other desperate souls who might steal from you. You slept on rooftops and in alleyways, exposed to the elements, and endured sickness without the advantage of medicine or a place to recuperate. You’ve survived despite all odds, and did so through cunning, strength, speed, or some combination of each.

Feature: City Secrets - You know the secret patterns and flow to cities and can find passages through the urban sprawl that others would miss. When you are not in combat, you (and companions you lead) can travel between any two locations in the city twice as fast as your speed would normally allow.

Personality Traits

"I hide scraps of food and trinkets away in my pockets."

"I like to squeeze into small places where no one else can get to me."

Ideals

"People. I help the people who help me — that’s what keeps us alive. (Neutral)"

"Respect. All people, rich or poor, deserve respect. (Good)"

"Change. The low are lifted up, and the high and mighty are brought down. Change is the nature of things. (Chaotic)"

Bonds

"No one else should have to endure the hardships I’ve been through."

Flaws

"I will never fully trust anyone other than myself."

Proficiencies Lifting & Carrying Racial Traits & Quirks
 * Armor - None
 * Weapons - Shortsword, Simple Weapons
 * Tools - Cartographer's Tools, Disguise Kit, Thieves' Tools
 * Languages - Common, Halfling
 * Skills - Animal Handling, Insight, Sleight of Hand, Stealth
 * Max Carrying Capacity - 165 lb. (15x STR score)
 * Push, Drag, or Lift - 330 lb. (30x STR score)
 * While pushing or dragging weight in excess of your carrying capacity, your speed drops to 5 feet.
 * Encumbered - 110 lb. (10x STR score)
 * If you carry weight in excess of 10 times your Strength score, up to your maximum carrying capacity, you are instead heavily encumbered.
 * Your speed drops by 20 feet
 * You have disadvantage on ability checks, attack rolls, and saving throws that use Strength, Dexterity, or Constitution.
 * Brave - Has advantage on saving throws against being frightened.
 * Lucky - When you roll a 1 on the d20 for an attack roll, ability check, or saving throw, you can reroll the die and must use the new roll.
 * Naturally Stealthy - You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you.
 * Halfling Nimbleness - You can move through the space of any creature that is of a size larger than yours.