Annalie has met Bot and it's day 90 yet I haven't had the Halloween event start yet. I've progressed a couple days already and still nothing :/
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Here are all the requirements:
-Finishing most of the dialogue while visiting clothier solo and buying a lot of clothes
-Met Annalie with bot
-MentalHealth > 20%
-Day above 15
-Bot likes you
-Hour in game 7 to 20
-10 days before or after Halloween in real life
Dialogues are random, so it might not appear on the first click. After this you will get two halloween decorations.(They appear in items->other) Try to put one on and you will get a second dialogue that activates the Halloween event.