"Clarissa left town. Game Over." Solution: You slept with Beatrice on Day 8. Clarissa has a "Townie Network." Never date within 2 miles of her diner.
try to romance all five women simultaneously. The game punishes cheaters with a "Rumormill" mechanic. If you date two women from the same social circle (e.g., Clarissa and Beatrice), you will get caught by Day 14. Milfs Of Sunville Guide
"I gave Naomi the locket, but she still ignores me." Solution: You wore the "Leather Jacket" to the meeting. Naomi hates leather. Reload and wear the "Suit" from the mall. "Clarissa left town