Simon was an incredibly intelligent boy, even if he had a stammer, one that his father could have been proud of, if not for his own wounded pride in assuming that no offspring of his should be “defective.” He went on to become a successful man, but he has done none of what anyone expected him to do. Lady Danbury is especially annoyed with him, because he hasn’t found a wife, gotten married, or sired children to continue his family line. Instead, he has focused on taking care of his tenants, generating a profit, and boxing. Simon is rather blunt in how he states things; he assumes Daphne bumped into him on purpose, and knows damn well who he is, and then banters with her whenever he sees her, from that moment onward. When Daphne needs an escape from a troublesome suitor, and he needs women to stop flocking around him peddling their daughters, he proposes a deal between them. He will pretend to court Daphne, and they can “pretend” to be in love so as to make “you more attractive to other men,” and make all the women think he is “taken.” To do this, he reasons, they must “appear” to be in love and sell it. So he coaches her on the physical things to do, to make it appear to others that they are together—little gestures and by staring deeply into one another’s eyes. He knows how to manipulate bystanders and convince them of his feelings, without truly understanding the depth of those feelings himself. He assumes himself not in love, and it takes him a long time to realize he feels differently—and even then, how he expresses this is through direct physical action—by grabbing and kissing Daphne. Their relationship is mostly physical—highly sexual, and it takes him time to learn to let down his defenses and become emotionally intimate as well. Simon is very direct, reads things on  surface level, and physical; he loves to ride horses, bed random women, and take out his frustrations in the boxing ring, where people bet on him to win. He also is willing to participate in duels and punch people who offend the woman he cares about. Simon is rather fixed in his single-minded desire not to have children, and uses that as a rationalization for not marrying Daphne, because she wants them and he does not. As Daphne points out, Simon has chosen not to have children “out of spite,” and to keep a promise he made to his father just to hurt him. Simon, however, is sensible enough to realize that Daphne is right, and he is avoiding the happiness that it would give both of them, and changes his mind. In his inferior Fe way, Simon is extremely poor at communicating himself to Daphne—he can’t nicely tell her why they shouldn’t see each other anymore (his emotions are involved, and Lady Danbury shamed him for not having good intentions), so he cuts her off without an explanation, abruptly, hurting her feelings deeply. He doesn’t want to court her around London nearly as much as she insists on it, but capitulates when she begs him to do so.

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Simon has two sides to his nature: a warm, likable man who can easily make Daphne’s little sister and brother absolutely adore the man who gives them a folded paper pony, and the man who attacks people and punches them in the face for insulting a woman’s honor or grabbing them. He can be quite pleasant and withdrawn, not wanting to draw too much attention to himself, and keeping Daphne happy with him by going along with her various demands (until she wants kids, and then he draws a boundary). He is also reluctant to truly get involved with life, since it takes him a long time to get married or have children. He distracts himself, prior to his marriage to Daphne, in physical pleasures and through having short-lived affairs. But push him too far, and he becomes angry, unapologetic about it, provocative in how he challenges other people, and will even beat someone to a pulp  if they deserve it. He will act out with people, and then feel chastised by any criticisms anyone he cares about levels at him, and withdraw again, or force himself to do “the right thing.”