Bart wondered what the hell had gotten into his son. Chuck was disrespectful, callous, and more often than not, dangerously tempestuous.
But he never stood up for anything, or ever tried to defend himself. If someone punched him he stood there and took it. He planned quiet revenge later but he never fought back in the moment. Which simply amplified the worry that the father in Bart was genuinely feeling all the more. Chuck couldn't afford to be infatuated with an Upper East Side princess whose aspirations reached to social climbing at this stage in her young life. These were formative years and Chuck needed to be focused, dedicated. One day he would run Bass Industries and he needed to know what it was to be responsible.
"You're a grown man, start acting like one," he kept an edge of harshness in his voice because if he didn't, he'd be pleading and then he'd have no power over his boy at all. He needed to teach him how to be responsible.
Not to ruin one of his few friendships for the sake of a quick tumble.
Bart blamed himself, for his own bad example. For the failure to find even a single constant woman Chuck could emotionally latch onto in his formative years. The string of mother figures who'd paraded through their penthouses had mostly been simultaneously bedded by Jack and that hadn't made the situation any easier.
Blair was different. Blair he'd known since they were so small, someone his own age with his own mental capacity. Bart had seen their slightly antagonistic relationship continue while true friendship subtly blossomed and he hoped that in her, Chuck had found more of a sister. That from his non-physical friendship with her, he would one day be capable of having non-sexual relationships with other female compatriots. Because he was going to need it. Or he'd never survive his first sexual harassment lawsuit – and being a Bass the real world was likely to throw a few of those his way.
"Listen to yourself," he cleared his throat to berate, desperate to get across to his boy just how important it was that he start to grow up. Bart wished he could make this easier for him, that he could protect Chuck from the harshness of the real world but it just wasn't possible. "You need to be paying more attention to your grades and focusing on becoming a meaningful member of society. You can't be a drain on your trust fund forever."
He was meant for greater things. Bart truly believed that Chuck was capable, he was smart and quick and much more observant of the world around him than he let on. If only he would stand up and take charge of his own life!
Bart felt doubly responsible – not because of the staff he'd chosen to raise Chuck, but because of the failure to produce any competition. Growing up Bart had always had Jack – his bitter, upstart younger brother whose nasty pranks and constant tattling had led to genuine bad blood between them. While that brother had been a thorn in his side until he left school, the competition had been what drove Bart, what pushed him to be better, wiser, more crafty than his sibling. He'd eventually given Jack his own, lower, place in the company, just to show that he'd eventually won.
Chuck had no such competition. Chuck had a trust fund which bought him everything he ever wanted without even having to go to the trouble of asking for it. His life was consumed with idleness and self-satisfaction. He needed to learn that emptying that pool of money wouldn't buy him everything.
"I'm not draining my trust fund," Chuck disrespectfully rolled his eyes, completely sidestepping the issue and misinterpreting Bart's words.
He wanted to play this game? Fine.
"Really?" Bart batted back. "There was a rather large outlay to a jeweller recently. I've yet to see this new watch or diamond cufflinks to justify such a charge."
He'd meant to throw the purchase in his son's face, to highlight that he was still shallow and naïve to think thousands of dollars on a watch could buy him respect from people who met him. But the attempt backfired spectacularly. Instead of shame from Chuck, the two teenagers eyes were drawn to each other, like sparking magnets. Then Blair smiled secretively, her bright eyes sparkled and he saw her meaningfully squeeze Chuck's arm. A genuine smile slowly lifted Chuck's lips until he was beaming. In that moment when he leaned over to kiss the young girl for the second time at this dinner, Bart began to doubt the plan he and Eleanor had come up with.
It was a soft, chaste kiss that he was horrified to see. The kind he had bestowed on the mother of his child two decades before, and no one since. Bart had thought there could be nothing worse for Chuck than letting his smart mind go to waste on partying and destroying friendships for the sake of satisfying his dick.
It occurred to him that actually, there could be something far, far worse. To follow in his father's footsteps and let himself surrender to love. An image flashed up behind Bart's cool, blue eyes. Of the beautiful woman he still loved in his heart, whose whispered promises of love had been the last strains of her voice that he ever heard from her, even as Chuck's newborn whimpering had drowned them out.
Eleanor interrupted the soft longing that had stirred in Bart's heart with a sudden terrifying thought of her own. God he would never want for his son what had happened to him in those early days of fatherhood.
"Is this why you're not taking Prince Theodore to the ball anymore? You two are going together? No, I absolutely forbid it," Eleanor struck out at Blair shrilly.
Bart's mind ticked over for a second. Cotillion? Why was that ringing a bell? Then he remembered that he and Chuck had come to an agreement about that particular ball. And Chuck was not taking Blair Waldorf as his date.
"You can't stop us," Blair shot back defiantly.
Clearly her mother's daughter.