Simon is up for a high-stakes caper, because he knows it’ll get him time with a beautiful girl. He’s opportunistic, looking for ways in his environment to move forward – whether that includes pretending to faint after being “shot”, to flirting aggressively in a public place, to wandering around the park looking for solutions to his problems, to snuggling up in a locked closet without a hint of stress over the dangerous, rather illegal thing he’s about to pull off. Simon notices his environment so much, he is mindful to measure spaces, take a swig from a bottle, or sneak into a chimney after fixing his tie. He admits, “I’m very perceptive” when Nicole says no one else ever noticed the family resemblance with the Venus before. He knows her father is guilty. He knows why she needs to steal it. He also knows that he wants her. His bunch of gadgets intended to get them out of the closet shows he’s thought ahead to all the potential outcomes and planned for their eventuality. Simon “knows people” and “human nature”, so his plan all involves “natural human reactions.” He’s already decided that Bonnet is going to retire, by the time the caper ends – there’s nothing for it, really. He is a master at creative thinking. Not only does he react quick on his feet, but he is also witty, with a love of wordplay. He can think himself out of a closet – literally. His “plan” involves noticing his environment (Se) and coming up with slightly ingenious, rather hare-brained ideas of how to set off the alarms in order to steal the Venus. He wants to understand things, which is why he interrogates Nicole so much about why this particular museum. Or…so she thinks. He is logic first and foremost, pointing out all the flaws in her ideas and plans, sometimes with melodramatic flair. “You’re crying to soften me up. It won’t work!” Oh yeah? It does. He can pour on the charm. He’s flirtatious, funny and enjoys setting people off. His understanding of how people work is what enables him to steal the Venus in the first place.

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Simon is surprisingly responsive to other people and their needs; when Nicole comes to him assuming he is a thief, he helps her steal the statue and clear her father’s name, then arranges for it to be whisked away elsewhere (at no profit to them) to keep them in the clear. Then he approaches her father and informs him that he is now an ex-art forger, choosing not to turn him over to the authorities. He is both skeptical of and unsure that robbing the place is the best idea, but then comes up with a safety-first way of doing so, showing his 7 wing tendency toward slight arrogance and enjoyment of taking risks. He becomes excited to do so, but still wants to keep Nicole safe in the process. He also has a playfulness to him—always cracking jokes, insulting people, and making fun of the situation, while finding ways to take advantage of the situation.