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So I am stuck with progressing Felicity & Emma and Ashley. Ashley has the talk action but says I must improve friendship with Felicity and Emma. They have the talk action as well but it says I need to improve friendship with Ashley. Did I do something wrong and get softlocked there?

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Only way for that to happen is to have skipped one of their story chains with a code. Said code specifically warns you things like that can happen.
You'll have to load a save from before using the code (check autosaves too; page left of the save slots, just as to the right has more save slot pages) or start a new game.

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after passing days for about 10min it took me to the winter cabin and that progressed it. We need a proper walkthrough for some of these things lmao.

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You can check the wiki, but as it will tell you, it just automatically happens. It shouldn't be confusing. I'm not sure how I could make it less confusing.