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We know that Sergay was studying in Windbloom at the time. Therefore, he probably joined the military AFTER he graduated and prior to that time he spent it with Mai. Otomes are what? 15 years when they enter 1st year and 16 when they graduate (Since Pearls are 2nd year students). Sergay, who is 25, adopted Nina 6 years ago when he was 19 and we know that at that time he was in the military.
Besides, watch episode 1-2, you can see just how much hatred there was between Sergay and Natsuki when they first saw each other.
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