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You were once in the employ of a noble or wealthy family, but those days have come to an end. While in their employ, you learned how to blend into the background and do as you're told, and you've become very familiar with the ways of the wealthy. How this service effects you is another question - You may be hardworking and quiet, meek and easily intimidated, or you may be scornful of wealth and power, knowing its corruption, and have little respect for authority. Perhaps you are clever and have taken advantage of your position to steal and gain information with which to blackmail others.

Work with your DM to come up with a character or family who you might have served. You might also consider how long you have worked for this family - have you worked for them since you were a child? Do your family also work for them? Or is it a newer posting? Have you moved around a lot? Do you like your employers or despise them? Was the noble house you worked in in the country side or in a city? Were you one of many servants or one of few? If you were one of many, did you lead the lady's maids or were you at the bottom of the food chain?

Why did you leave this person's employ? Was it reluctantly or by choice? Where you caught pickpocketing or framed for a crime you didn't commit? Did the family fall into disgrace? Did you follow a lover or go to be with your family? 

Consider also the significance of the person you used to serve - Were they important or insignificant? How did this effect you?

 

This background allows you to establish connections with the politically influential of the world without having influence or wealth yourself, and may give you insight into the character and secrets of various important people.

 
Skill Proficiencies:

Choose two: Sleight of Hand, Stealth, or Insight

Tool Proficiencies: Calligrapher's Supplies, Weaver's Tools, or Forgery Kit.
Languages: One of your choice.
Equipment: Calligrapher's Supplies, Weaver's Tools or Forgery Kit, a candle and tinderbox, 10 gold pieces, and a small collection of objects either stolen or given to you by your former employer.
 
Feature: Clever Camoflauge

You are used to blending into the background as you carry out your duties. You have a keen ability to blend in in cities and busy buildings and easily fall in with servants. Fellow servants are willing to talk to you, put at ease by your understanding, and help you as they can. You can get in the backdoor of most populated castles and houses with help from servants, though they may be reluctant to let you in further than the kitchen and will likely not allow you companions to enter as well.

 
Suggested Characteristics

Lady's maids may have a variety of personality traits, but they are used to rougher living, taking orders, and blending into the background. They may have a variety of bonds — loyalty to the family or noble they served, a desire to provide for family, to protect friends, or perhaps a cultivated lack of respect for authority. 

d8 Personality Trait
1 I have a habit of picking up dropped trinkets and collecting uneaten food.
2 I regale my friends with gossip about famous knights and members of the royalty.
3 I have little respect for authority figures and am not easily intimidated by those in power.
4 I often eavesdrop on the conversation’s of others out of habit.
5 I rarely speak when not spoken to and am hesitant to speak my true opinions and feelings.
6 I tend to disappear in a crowded room, becoming part of the backdrop with ease.
7 I often casually pry into people’s business to discern their secrets for blackmail later.
8 I have been mistreated by authority figures and have learned that it’s a dog eat dog world.
d6 Ideal
1 Status Quo. Status is defined by clear rules which are the foundation of civilization. (Lawful).
2 Change. The low are lifted up, and the high and mighty are brought down. Change is the nature of things. (Chaotic)
3 People. I help the people who help me — that's what keeps us alive. (Neutral)
4 Retribution. The rich need to be shown what life and death are like in the gutters. (Evil)
5 Loyalty. I am loyal to those who have helped me and will never betray them. (Good).
6 Aspiration. I'm going to prove that I'm worthy of a better life. (Any).
d6 Bond
1 I am in love with a lord or lady but courtly rules prevent us from eloping.
2 I have great respect and fondness for my employer, although they are not what they once were.
3 I was mistreated by my employer and hope to someday return and take revenge on them.
4 I worked for many years to support my siblings/ailing parents.
5 I stole from or blackmailed my previous employer and fled their home before I could be punished.
6 I know many secrets thanks to my innocuous presence in intimate social environments.
d6 Flaw
1 I do not share my things with friends, and I will fight to keep personal belongings within my full control.
2 As a defense mechanism, I lie and misdirect everyone around me, and steal and hide anything I can.
3 I think myself better than other common people because I have experienced more sophisticated surroundings.
4 Being used having little, I now cannot stop myself from reveling in material pleasures.
5 It’s not stealing if I need it more than someone else.
6 I don’t believe that those in power are honest or trustworthy and will not hesitate to undermine them.
 
Variant Servant: Scribe

Having some education, you were employed as a messenger for the noble you served. You can read and write and were entrusted with many secrets. You have a great ability to find shortcuts through cities and castles. You have a keen memory for things you've overheard and can write swiftly.

Choose proficiency in Calligrapher's Supplies, not Weaver's Tools. 

Include in your equipment Calligrapher's Supplies rather than a sewing kit.

 
Variant Feature: Entrusted Messenger

You may select this feature instead of Clever Camouflage. You have been entrusted with many secrets and have learned to read and write certain codes. You have advantage on decoding new cyphers and on creating your own. You also learn one additional language.

 

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