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Bonnie was a child of two very different worlds. Sir Bentley Shepherd, her father, was the sort of stiffly honorable man that seemed to believe that one couldn't even crack a smile or make a joke without somehow undermining the seriousness of one's duties. Even if those duties weren't particularly serious. But time and again, she was grilled on obligation, duty, responsibility, honor, and a dozen other roughly equivalent synonyms that made for life's most tedious thesaurus and childhood. Her slightly older brother, Malcolm, even caught more of it as the first born, but Bonnie decided from an early age that a knight's life was not even remotely for her. Yes, it was incredibly fascinating how a few hundred years ago they were part of a ducal line that was dishonored and cast out, and there still was a line of Shepherds that ruled a duchy, but it had absolutely nothing to do with her. On the other hand, unlike her brother, Bonnie took to the sword fighting practice with her father with as one of her first passions, though it was maddening to her father when Bonnie veered away from his knightly style and leaned immediately into the flamboyant, flashy Lycene duelist style that her mother Andromeda had mastered as a retired member of the Champions Guild. It was her father's loud condemnation of it that was the start of several fights that led to his divorce, and Andromeda running off to be a pirate. For Bonnie, this was a reminder that you can't please everyone, and set her on a fiercely independent path. After a few more years of trying to make it work with her father, the provincial and tedious life and constant lecturing about disciplined living just proved too much, and she set off to find her mother. Turns out, having an incredible natural talent with a blade, a scoundrel's flexible take on morality, some natural charisma, ambition and a very capable teacher really makes for a winning combination in being an exceedingly successful Naval Acquisitions Specialist. Her start at privateering startedly with (mostly) legal exploits such as fights with Abandoned raiders, acting as a sellsail, and convoy guarding, but she's fairly confident there's at least a half dozen smaller domains with grudges it would be unwise to visit. After her mother's comfortable retirement (the beaches in Setarco -are- very nice, she writes), Bonnie acquired quite a few names for herself (Black Bonnie? Bonnie the Red? Bonnie the Fashionable? Why are the memorable ones not repeatable in polite company?). She also acquired one of her best friends, Simon, an author and adventurer she rescued from Grazagh the Incoherent, an Abandoned Chieftain of the Deeptides clan. A few letters back home from an increasingly despondent brother convinced Bonnie that it was time for a change, and she and Simon went home, rescued poor Malcolm, and founded the adventuring (and sellsword) company named the Valiant Effort. The name was definitely her idea, and don't believe anyone claiming otherwise. She fully expected to do questionable deeds for adventure and profit as a former pirate for the rest of her days, and definitely never expected to hear from her father again. And she especially didn't expect to hear that the old, stuffy warhorse had apparently reconciled with the noble line of the family, become the house sword, died in glory, and been posthumously ennobled and had Malcolm declared heir. With her also ennobled with him. The idea was preposterous to her. But all right. She'll see this through. What's the worst that could happen?

Bonnie's got the kind of smile that makes folk nervous. Not because it lights up a room (though tis bright), but because it's so big. She keeps her lips rouged, and that wide grin shows off her white teeth and honestly looks a little like she might be considering taking a bite out of something. Or someone. It speaks of a hint of edge that is belied by her sweetly round face and big, warm eyes. Her hair is red-haloed dark and curls and waves wildly to her shoulders, and her skin is sun bronzed. She's got a strong nose with a button tip that is just a touch crooked, as if it has been smashed once or twice in her life, and a swagger to match her statuesque frame. This is no willowy woman; thighs and arms stacked with compact muscle she has no qualms about showing off.

With a sublimely self-confident swagger and utter fearlessness that could verge on the reckless, Bonnie is a woman unaccustomed to seeing any setback or difficulty as anything but an intriguing challenge to be tackled. An unapologetic bon vivant, Bonnie is a connoisseur of all that life has to offer, and laughs off social mores or a sense of shame in the pursuit of whatever catches her fancy.