Jessi was born one of three triplets in the Twignut family. Growing up alongside her more rowdier sisters, Jessi was always the quieter and far more reserved, and spent her time reading books instead of playing with the other children. She would often be found tucked away in the deepest corners of her house, perusing various tomes and literary works, and that what was left in her wake would be spotlessly clean rooms and hallways, indicating some measure of obsession with cleanliness.

Although the Twignut Triplets' history is seldom made public, since the early years there have been unsettling stories circulating around Bree-town about Jessi, describing troubling, unchildlike behaviour from a young age, such as the time an eight-year old Jessi casually stole a girl's toy doll and burned it in a fire.

"The Twignuts? Mad lot, those triplets. Ye seen the eldest, Jessi, right? Somethin' ain't right with her, I'm tellin' ya. Somethin's wrong with all of 'em! Look at that other girl, calls 'erself Eony.... keeps dancin' 'round and behavin' like a child. I've even seen 'er switch from dancin' around in joy t'cryin' like a little babe in the blink o' an eye... Mad lot, those triplets."

- A sample of local Bree-town gossip regarding the triplets