: Re: How to write a corporate character that likes to toy around with his colleagues? I want to write a male, corporate working, character who is always cheerful and smiling, no matter whatever the

@Holmes449

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Misery Loves Company.
I think you'd have to make him, at least apparently, very observant and intelligent.
One way to make him hated and cheerful at the same time is to have him tell jokes about his co-workers, that hurt. To do that, he needs to be able to read their emotions, tell when they are hurting, and be able to figure out why.
You could make him a good hacker and spy, something he has hidden from his co-workers. He wears earphones a lot, like listening to music: But what he is listening to is private conversations of his fellow employees on their cell phones, or office phones. The equipment to do that kind of intercept and relay does cost 00s, but he considers it part of his entertainment system.
He knows when people are having trouble at home, with money, with medical issues, with their spouse, with their kid's drug addiction, and he is clever enough to make jokes about this stuff that denigrate people that get into too much debt, or have erectile dysfunction or can't control their own kids or are obese and can't lose weight, but he does it in a way that prevents them from knowing they are being overheard.
Perhaps he goes further, and by occasional viewing of somebody typing a password, he is able to get enough clues about the password (number of letters, approximately where on the keyboard they are) that some available dark web password breakers give him access to the personal emails of his co-workers. So he can read those, too.
Perhaps he goes even further than that; hiring experts to put up hidden spy cams inside of people's homes. Contrary to what TV tells you, it is not difficult at all for experts to both encrypt and hide the final destination of such videos. Perhaps he wants to catch some nude pictures of his coworkers, or other bedroom activities. Material he can use anonymously, perhaps, or just know what might embarrass somebody. One of his dreams is to catch somebody cheating on their spouse or boyfriend or girlfriend. Heck, he may even hire a high end prostitute (one that doesn't look like a prostitute) to seduce a coworker's boyfriend, and then out him to his coworker with pictures to prove it, and ruin her relationship. All in fun.
The truth is he is miserable, he resents happiness, and enjoys punishing happiness or ruining it. That is his hobby. And like many people, he doesn't mind spending many thousands of dollars on this hobby, just for the fun it will bring him. It isn't about the money, it is just about making other people as miserable and lonely and empty as he is.

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