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Silas Cunningham is a nepo baby who resents his father and will flirt with anyone he finds attractive, which just happens to be most people. Not only is he flirty, but he’s also charming and persuasive, a trait he learned from spending his developmental years schmoozing with rich people and being flaunted by his father as the next politician of the city. He doesn’t genuinely like most people, not out of spite like Wendy, but out of experience with the true selves of wealthy assholes who laugh over caviar while their lackeys for hire are busy leveling a poor neighborhood. He likes a challenge; he likes when someone puts up a fight and doesn’t immediately fall for his charms or money…which made Wendy quite intriguing in the eyes of a man who frequently gets what he wants with little resistance.
Silas was raised in an inner-city mansion, close to important government buildings and fellow politicians. He interacted with more adults at elections and galas than kids at school, leading to a lack of emotional intelligence when it came to his peers. Sure, he could make a girl blush within two minutes of meeting her, but when faced with a distressed or worried lover, he’s left scrambling and fumbling for a solution that isn’t just buying an expensive gift or lavish vacation. Every partner he’s had has left him, either due to his inability to express a sincere emotion or because they didn’t want to deal with the baggage that he came with. He’s shallow and he knows it. He was raised not as a son, but as an heir. He wasn’t made to have depth or character, just simply as a means to carry on the legacy of corrupt politicians in a suffering city. His father was either distant or overly involved, only interacting with Silas to make sure he was keeping up with his studies and to criticize him whenever he expressed hesitation at the fact that his whole future was laid out for him. His mother was more present in their gardener's life than her son’s, often appearing at mealtime to drink excessive amounts of wine and then pass out until the next public appearance where they had to act like the perfect nuclear family instead of a disconnected mess of secrets and lies.
When his father found him making out with another politician’s son, he made sure the press kept quiet. Money was a great incentive after all, and he couldn’t risk Silas having a public scandal such as that one. Tax evasion was fine, but homosexuality? That’s a big no... Now, they were in a stand still. Silas refused to fully commit to his politician duties as he much rather preferred to bother Wendy, yet his father refused to let Silas be free, trying desperately to manipulate his son into following in his footsteps. Silas doesn’t know what he would even do if his father did leave him alone or disown him, so used to living in luxury that he doesn’t know who he is without it. For now, he finds joy in Wendy who barely tolerates him and his shenanigans but also doesn’t care who his father is and doesn’t expect anything from him. They can simply exist without societal pressures and familial connections, even if neither of them has enough maturity or self-awareness to realize how important they are to each other.