I have big news when it comes to Custom Answer Saved Questions. the villager's personality does not seem to have anything to do with the question he is going to ask you. he may ask you the same question twice in a row (but never more than once every 3-4 days), but with different possible answers. usually there are 3, plus a personalized response written by you, and the option “none of the above”. I have noticed that some villagers are less inclined to ask you a saved personalized answer question. It happened to me to have 3 times in a row the same villager who asked me the question of the day, and 2 times in a row the same with however different proposals of answer each time. to make the dialogue in question easier to have, I advise you to remove all clothes on you so that he does not talk to you about your outfit, and not to hold any object so that he does not tell you about it either . but it is very possible to have the dialogue even if the last two conditions are not met. moreover, you will sometimes have to speak 5 times to a villager before he asks you the personalized question of the day, but never more than 6. otherwise it is another villager, or it is not on the right day, for example if you already had the personalized question the day before. unfortunately, you cannot choose which question you are going to have. it's random, you have to be patient.