Wait, hold on, why the double chat bubble? What did the Grand Duke actually hear?
basically the "system" took over the grand duke that day. kinda like how ishis (the kid who changes into a woman and man at certain times of a day) controlled the mc.
the grand duke reenacted the scene and remembered that he in fact did not say "cherish you" but said "despise you" because of the system taking over preventing the mc to achieve the grand dukes greatest dream. which is why theres two speech bubbles.
Kyaaaaaaaaaa (≧∀≦)