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This wasn’t correct even before then lol.
Royalty would marry for diplomacy, whether externally to other royalty, or internally with powerful nobility.
Wouldn’t any woman he marries be a princess?
right, but as @ImWaitingForRetcons@lemm.ee says, they used to marry to make allegiances happen, so his dad is looking for him to marry a princess so that they can join the kingdoms and grow in power