Courtesan

You are well practised at ingratiating yourself into any company; clever conversation is your weapon of choice. You know how to put people at their ease, how to entice them, how best to flatter and charm them, and make them feel like the centre of the world. You can draw secrets and confidences out of them, should you choose, or use your charms to convince people of almost anything - so long as it's something they'd already want to beleive, and you know when people are trying to trick you.

Skill Proficiencies: Two from Persuasion, Deception, Insight, Sleight of Hand, History

Tool Proficiencies: One type of musical instrument

Languages: One of your choice

Equipment: A musical instrument (one of your choice), the favor of an admirer (love letter, lock of hair, or trinket), a Set of Fine Clothes, and a pouch containing 15 gp

Suggested Characteristics

Successful Courtesans have to be able to capture and hold attention, and tend to be beautiful, confident and self-assured. They are not necesarily callous, but they are used to placing a value on their time and abilities. Flaws might come from arrogance, disdain, or a lack of self-awareness. 

d8	Personality Trait
1	I long for a real connection, a proper romance.
2	I prefer my friends to be people of power and influence.
3	My eloquent flattery makes everyone I talk to feel like the most wonderful and important person in the world.
4	I always look my best, no matter the situation.
5	I'm not just a pretty face, and I'll do anything to prove it.
6	My loyalty is hard to win, but once it's won, I'll do anything for my friends.
7	I don't beleive in love. It's a childlike notion.
8	I'm impossible to shock. Whatever it is, I've seen something more scandalous.

d6	Ideal
1	Love. Everybody should get to experience that connection. (Good)
2	Power. The more influence my clients have, the more they can do for me. (Evil)
3	Change. Nobody is fixed as they are, we all have the power to grow. (Good)
4	Greed. I’m only in it for the money and fame. (Evil)
5	People. I like getting to know others, even if it's for a short time. (Good)
6	Pride. I know my value and my worth, and that other people see it too. (Any)

d6	Bond
1	I am ashamed of my work, and will do anything to keep my past a secret.
2	Redemption. Everyone deserves a second chance.
3	I fell in love with someone I can never have. I'm running from that truth now.
4	Somewhere out there, I have a child who doesn’t know me. I’m making the world better for them.
5	I will do anything to prove myself superior to my hated rival.
6	I would do anything to help out someone down on their luck.

d6	Flaw
1	I love to be notorious. Anything that wins me fame is a good idea in my book.
2	I'm too easily distratced by a pretty face.
3	Scandals seem to follow me around.
4	I'm never satisfied with what I have—I always want more.
5	I have trouble keeping my true feelings hidden. My sharp tongue lands me in trouble.
6	I've spent too long faking interest in others, and no longer know how to be genuine.