Simply talking to characters isn't always enough.
Focus on school lockers and home computer activities. Visit the gym and Diana.
Given the multiple endings and the significant impact of player choice, it's a good idea to save your game frequently. This way, you can explore different story branches without losing progress.
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Walk to the northern outskirts during an evening slot after your total gold exceeds 500.
To unlock her explicit scenes, you must raise either her Affection to 50 (Pure Route) or her Corruption to 40 (Corrupted Route) by visiting her at night. Evelyn (The Mayor's Wife)