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You have to advance the time to that specific time slot. Then wait a minute or two for her to walk there. It'll take her some time to walk there. After the pool event, she will disappear and you have to do the same thing the next day.
I think the problem is that this character is a save file from before version 1.0. It was said in the update notes that there will be bugs with older save files before the full release of the game.