Rupert Fleming had to be tough from a young age, given his chronic health problems. He wasn't too active of a kid, had numerous food allergies to avoid and medication he had to keep on hand, but this made him a self-sufficient young man with a calculating mind. And he really came alive around Halloween.
For a boy that lived daily with certain medical fears, the time of year where everyone reveled in scaring the pants off each other was a great equalizer, and the frights resonated with Rupert who already had to face several of his own fears.
Not being as active as other kids had left Rupert with an impressive collection of movies, video games, and other literature amongst his chief interests. Horror and spy fiction, for starters, about anything where the protagonist had to survive and navigate via their wits and guile. It was a lifestyle Rupert aspired to, to live beyond his condition, and while he wasn't strongest or most popular of the other kids at school, he had his area of expertise. And quite the shrewd, scheming mind.
His current obsession was unraveling conspiracy theories. Rupert, true to form, had gone the full cork board and string approach to tracking unusual events he read about online, with ties to where unexplained or horrifying phenomena tied in with his favorite movies.
Rupert prided himself for prepping for any eventuality, both ones he caused or experienced. He wasn't a delinquent troublemaker, however, although he relished the chances to let loose with deceptions and pranks, and Halloween naturally allotted these kinds of events.
He wisely considered that his scheme to pull off his own disappearance wasn't the most practical use for his schemes this year, and logistically it would be hard to maintain his health without leaving traces. But there were surprises in store for his friends even they didn't know about. yes indeed, all of Rupert's planning would come to fruition during Halloween, as he would eagerly think of next year once the calendar turned the page to November. He would challenge his limits, even if that skirted the line to pushing the envelope. And Rupert would be ready to face them.
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