In your earlier days, you were a figure of modest yet undeniable influence in the cozy corridors of halfling society. Whether nestled in the green hills of the Shire-like Delver's Vale or the bustling halfling quarter of a larger city, your charm, cunning, and conversational flair earned you a place of privilege. You might have been a respected member of a local council, an advisor to a burrow-mayor, or an administrator in a halfling trading consortium.

Unlike many who rise through noble birth or military service, your status came through cleverness, courtesy, and an uncanny ability to remember names, birthdays, and favorite pipeweed blends. You were at the heart of the social web — organizing seasonal festivals, smoothing over feuds between merchant families, or seeing to the quiet redistribution of wealth "for the common good."

Though you've since taken to the road, whether out of boredom, scandal, or a yearning for something more than garden parties and estate ledgers, your reputation and connections remain. Your former colleagues still recognize your influence, and you can navigate genteel society with ease.

Skill Proficiencies: Insight, Persuasion

Tool Proficiencies: One type of artisan’s tools or musical instrument

Languages: Two of your choice

Equipment: A fine set of clothes, a signet ring or family crest brooch, a keepsake pipe or heirloom trinket, and a belt pouch containing 25 gp

Suggested Characteristics

Well-off halflings often blend courtesy, cunning, and a deep appreciation for comfort and civility. They might mask ambition with a smile or take genuine joy in helping others live well.

d8	Personality Trait
1	I always know the right fork to use at dinner — and the right words to use in a debate.
2	I try to make everyone feel at home, no matter where we are.
3	I speak in anecdotes and metaphors — the more rustic, the better.
4	I loathe conflict and will go to great lengths to keep things civil.
5	I collect little luxuries: tea blends, fine buttons, scented candles.
6	I’m a bit of a gossip, but only with the best intentions.
7	I never forget a slight… or a birthday.
8	I always look for the silver lining, even if it’s in someone else's pocket.

d6	Ideal
1	Comfort. A life well-lived is one spent in ease and good company. (Good)
2	Tradition. Halfling ways are worth preserving — they keep the chaos out. (Lawful)
3	Ambition. I left behind comfort for greatness; I won't return empty-handed. (Any)
4	Charity. Wealth and status mean little if they aren’t used to help others. (Good)
5	Cunning. A quick wit and a calm voice are sharper than any blade. (Neutral)
6	Curiosity. I want to see how big the world really is beyond our hills. (Chaotic)

d6	Bond
1	I’m still writing letters to my aunt back home — she expects updates.
2	A scandal forced me out of my comfortable life; I’ll set it right one day.
3	A former mentor believed in me. I won’t let them down.
4	I helped cover up something serious in my old community. It may come back to haunt me.
5	I swore an oath to a local lordling or matron — I must uphold it.
6	My family name means something, and I intend to keep it respected.

d6	Flaw
1	I can be patronizing without realizing it.
2	I’m deeply uncomfortable getting my hands dirty — literally or figuratively.
3	I fear losing my social standing more than I fear death.
4	I hoard small valuables and call it “saving for retirement.”
5	I rely too much on charm to solve serious problems.
6	I always assume people like me — even when they don’t.