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Current Likeability observations
This kind of relates to what you're talking about; but it was discovered that the conversation responses follow a sequence. (1-97, before starting over) I translated a KR "cheat-sheet" for the correct answers to each, if anyone wants to format that into this page somehow since I don't have the patience.:
https://docs.google.com/spreadsheets/d/1DXzHjpuvuVZvkbyfE_31tG6knjdY5nswfyEl2RZdYno/edit#gid=0
I think there are multiple such spreadsheets based on an original korean one, but there is a note there about special conversations which occur at prescribed intermediate likeness levels. In my own experience, triggering one of those seems to advance or jump to an unexpected part of the sequence.
Additionally, though it might be my own mistakes in keeping track, I have been following it and have observed possible errors in the table (that might be caused by the special conversations). Otherwise it has bee mostly right.
Another user on the Nexon forums claimed to have made it completely through it without issue. IMO it typically seems to be user error, and I haven't personally had any problems. Albeit I'm only at mid-60s for responses.
i have had problems surrounding special convos for dai and eirlys, but the sheets match. My most successful run was elsie, with only one hole. but talking to multiple people it's super easy to forget to cross off, esp when the special convo can replace an entry so if they claim to have made it i'll definitely believe them.