Because, in the end, it was just a race. They had all had a chance to claim the grand prize, and most of them had tried to take it. Out of six possible competitors, four of them had an interest in the prize, and all four had, in their own ways, jumped at the chance to claim it.
Hikaru was the first, of course, even though he didn't know it until much later. The incident in Karuizawa had been proof enough of his feelings. He tried again during the spring semester of their second year at Ouran, when he had become more comfortable with his own feelings. He was rejected, with a genuine smile and no ill will—because she was Haruhi and she had the ability to comfort you even as she broke your heart—but it was still a rejection.
Mori-senpai was next, during her first year at university, and he knew—from the moment that he offered her dinner, a movie, dancing, whatever she wanted, he knew—that she would say no. Knowing Mori, it hadn't been a real offer anyway, just something he'd done to appease his cousin. Perhaps Hani-senpai had talked him into asking her because he only wished to see him happy, no doubt harboring some childish notion that people were only truly content with life when they were in love. And yet, Mori had done it. He was rejected, with an understanding smile and a similar wish for his own happiness—because she was Haruhi and she only ever wanted the best for every single person she'd ever met—but it was still a rejection.
Tamaki's attempt had come on the night of her graduation from law school. They had all been in attendance and had gone out to eat as a group to celebrate her accomplishment. Hani-senpai and Mori-senpai had left first, very early in the evening, because they'd ridden together and Hani had received a frantic call from his fiancée. Something had happened, and she was scared to be without Hani and Mori. Kyouya had met her once. She was a useless girl, and he was sorry to see someone like that foisted on his friend.
Hikaru and Kaoru had come separately, but had left together. When their mother had died unexpectedly a few years before, they had both proudly continued her legacy. Kaoru had gone to Paris to wrap up some unfinished business, and had stayed because of Jean-André, while Hikaru took care of things in Tokyo, and stayed there because of Hanako and his own surprising set of twins. They hadn't seen each other in months, and while they were both happy that Haruhi had finally realized her dream, this dinner was also just an excuse for them to see each other, to visit with one another and catch up until Kaoru's return flight to Paris the next evening forced them apart again.
"We've gotta get back," Hikaru said, not even glancing down at his watch. "It's getting pretty late, and it's my turn to read the bedtime story."
Kaoru leaned over and gave her another hug. "Congratulations again, Haruhi," he said. "Sorry we have to leave like this."
"You are not," she replied, mischief shining in her eyes. "I can tell when you guys get impatient, you know. Just…no more twincest, okay? It was creepy then, and it's creepy now. It's like some kind of nightmarish flashback that I could do without."
"Don't be such a party pooper, Haruhi," they harmonized, leaning into one another. "Come on, you know you like it." They laughed softly as Haruhi rolled her eyes. They held hands as they walked out of the restaurant, earning a few whispers from the other patrons.
That had left the three of them, talking and reminiscing and finishing off the wine that someone had ordered earlier. Kyouya's phone had started to ring rather loudly, and he excused himself to take the call. It had turned out to be a trifle. He planned on firing whatever idiot was responsible for making him stand out in the cold rain to deal with something so insignificant. When he came back inside and started walking to their table, Tamaki was lowering his head to cover Haruhi's, and his right hand was gently cupping her cheek. Kyouya leaned up against a wall and watched them, forcing himself not to disturb Tamaki's moment.
"Do you need anything, sir?" one of the restaurant employees asked him cheerfully . He ignored her until she walked away.
They didn't kiss for quite as long as Kyouya had thought they would. Haruhi moved away first, and the sinking in his stomach lessened. She smiled, and Kyouya knew what was coming next. Part of him reveled in it. The other part of him made a mental note to avoid Tamaki's calls the next day.
"Tamaki-senpai," she started, and Kyouya saw the unexpected wetness on her cheek. She looked away from Tamaki and spotted him watching them. She wiped her eyes and turned back to the overeager blonde in front of her. He was rejected, with a heartbroken smile and tearful apologies—because she was Haruhi and although she had loved him since high school, she also knew that being with Tamaki could only ever end terribly, no matter how much they loved each other, because his grandmother despised them both—but it was still a rejection.
They'd gone their separate ways then, the three of them, and it wasn't until someone sued him years later that Kyouya saw her again. The accusations against him had no legal foot to stand on, and Haruhi realized it the moment she looked at the case file. Both parties had met to discuss a settlement, because it was worth settling to avoid the press, and after the meeting was adjourned, it hit him that Haruhi must have sabotaged her client's case to arrange the meeting in the first place. He looked up her home phone number and called to ask her why.
"Kyouya," she replied, "did you honestly think I was going to let this client go up against you? Your lawyers would have had a field day in court with her. She was going to lose the case anyway, so why not save her some psychological damage by avoiding court altogether?"
He smirked, a little more smug than he had the right to be, and asked, "Are you free tomorrow?"
"In the evening, yeah," she replied absently, and he heard the familiar sounds of paper being shuffled around. "Why?"
He allowed his smirk to become a grin, told her the name of the most expensive eatery he could think of, and hung up.
Because, in the end, it was just a race. And Kyouya had more than enough experience in chasing after what he thought could never be his.