An unmarried man over thirty is considered to be untrustworthy by his colleagues who believe such men have not been conditioned to learn the fundamental principles of cooperation and responsibility; marriage makes the implicit statement that a professional male intends to stay in the family business.

Kyoya Ootori, being the pragmatic man that he was, knew the merits of marriage—not only to himself and his standing, but also to his family and their business interests. While he was still a considerable distance away from thirty, Kyoya knew that with his father's imminent retirement he would need to stack the deck in his favor, and he knew that part of gaining that favor would be to marry a woman that would provide additional gains for the Ootori family.

When the issue of marriage—and subsequently marriage interviews—finally became a topic of conversation between Kyoya and his father, he played his part and agreed to look over the profiles of eligible young women.

He was not surprised to find that each candidate his father had selected was a perfect mixture of pedigree, beauty, and accomplishment; quite a few of the selected profiles were those of girls he had gone to school with, and while he believed that they may have matured since Ouran Academy, Kyoya could not help but see them as the same frivolously-minded girls who had frequented the Host Club. He refused to waste this valuable opportunity on a woman whom he could not respect, but to Kyoya's advantage the girls he knew from his time at Ouran were not of any outstanding benefit to the Ootori family, and while they may have held some merit, Kyoya knew that marriage was not the only avenue open to form an alliance with their families' companies-should the need arise.

Out of a sense of respect for his father's choices in potential brides, Kyoya managed to select a small handful of girls he could potentially see as his wife. He was familiar with most of the young women, having met them before at social events, and in his short interactions with them they seemed to be at least tolerable companions.

So Kyoya returned to his father with the list of women he found acceptable, his father seemed to be somewhat pleased with his selections, and appointments were arranged to meet with the potential brides and their parents.

Each of the meetings went well enough, and from a business standpoint marriages with each of the women would prove very fruitful for the Ootori Group, but for reasons Kyoya could not fully explain he just could not imagine himself being married to any of the women he had met. While all of the women he met were each beautiful and accomplished he felt no attraction towards them on any level; it was not just the lack of attraction, but rather the frivolity and lightness that the women seemed to take towards such a life-altering decision. It seemed as if all of them had empty-headed fantasies about their marriage turning into some deep, abiding romantic love like that in a shojo manga, and Kyoya needed a woman that understood that their marriage was-at its core-business.