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If you lost while fighting the spirits, or else if you play for 30 in-game days, you can meet her at the hospita.

Last update I think. I treat it as a one time thing to be done at the endgame (e.g. once you have purchased everything else in the game)

Also restroom at the park. You need to buy the key first from the comic store.

Edit - the ones I ve found so far are

• Nightclub,
•  restroom at park, 
• downtown streets, 
• nurse's room in hospital, 
• outside kens home, 
• mall 

(some of these like mall and street requires specefic outfits that should have been purchased from the mall clothes shop)

First tell her you need more time. She'll wait at the hotel. then at the start of a new day, Make a save and try one option. Then load the save and try the other option.

For the latest update, I have no content for some of the events:

Easter - Happened on a Friday. On entering the hallway for the first time the scene to go to church triggered. There are decorations in the house but no events trigger. Visiting different rooms in the house also do not trigger anything.

Josef's birthday - It was a Tuesday so the bath audio played when entering the hallway, but no event triggered. There are balloons in the hallway and I can visit him in his office and wish him, but there is no other scene.

Anniversary - nothing - no decorations, no special scene triggers.

Adrian's birthday - It was a Monday so on entering the hallway the normal scene of Charolette talking Adrian triggered, but no event triggers. There are balloons in the hallway.  but there is no other scene.

I had no issue with christmas and the new years scenes.

Ashley is at lvl44 and has an exclamation mark on the info screen, but i cant seem to trigger her event.
Everyone else is maxed out
I'm not sure how to proceed from here.
Anyone have any tips?