Look for a large red heart with stars around it after giving a gift; if the stars are missing, the gift was not the right type for her.
Requires loyalty. Stall for time, lie about liking your job, and focus on jewelry gifts (earrings/necklaces). Advanced Tips File: Lovely.Overseer.Dating.Sim.zip ...
To pursue Kira, focus on Office Work and Training Guards on specific days (e.g., Office on Day 3, Guards on Day 17/18). Unlike the main girls, her path is often independent of how well other students pass their exams. Look for a large red heart with stars
Prefers a firmer approach ("go hard" or "instruct with force"). Your superior/Mistress if the stars are missing