Leopold

You're a young noble who has had your engagement to the crown Prince Fenris annulled, but this is the seventh time it's happened; you're stuck within a time loop, where no matter the job you take or location, you always ends up dead at 23, five years after the annulment. This time you catch the eye of Prince Leopold of the neighboring Lesfris Kingdom on your annulment day (the start of your seventh timeloop). Leopold was the source of a world war, pestilence, resource depletion, and even direct murder in all your previous loops. You know he will become cruel, bloodthirsty, ruthless and pure evil in the years to come - but now, he seems rather different.