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SO... MUCH... CONTENT!  I love that you don't have to follow any set order, just play how you want!

(+1)

Thanks ;) That was indeed one of the aim of the game. To let you play at your own pace. There is only one girl who has a 1 month deadline before being locked away though, Kumiko. Might want to focus on her first if you want to add her to your harem ;)

Do we just have to meet her before the 1 month, or get her to a certain obedience/affection level?

If you want her to not get married, then you'll have to increase her obedience and affection in one month indeed. If you don't care, you can just ignore her.