As Anastasia remains unresponsive, Rupert takes time to know what wrong he has said.
As far as he knows, girls her age tend to be very impressed by guys like Zen. But then again, he does not know anybody who is not. Even their enemies back then were all astounded by his remarkable attainments.
Even though Zen entered the military much later than most others, he worked hard to get recognition. Their aim there was to have him join the special elite force as soon as possible. Since the Catalysts that time were still in the middle of recruiting members, they did not have any other means to go outside of the fortress without alerting the higher-ups.
Overall, Zen needed to enter the special elite force in order to participate in the search mission for Anastasia.