The worst match is actually the best choice for his situation. As it is, it's a women only battalion (or whatever it was), so he has a whole lot of fitting in to do. If the knight-captain is known to be especially strict and he can still win her approval, it will definitely make things easier for him among all the soldiers in the unit. On the contrary, if he seemed to be relying on the princess's prestige/authority all the time, it would be more likely to give him a phoney approval from everyone, tied to the respect all the soldiers have for their commander.
@XieShu They are all also very proud of their chest, despite being professional soldiers.