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Hey, there also a couple of more triggers you have to fullfill that are basically progressing their story.
you have to see cookie's drinking event (the point and click one), have a drink night with cynthia and cookie and then see the event where cynthia is teasing you and cookie about 'something'. Hope it helps!

I have all the events open except for this one and I have reviewed all the events with Cookie and all the events in which she participated. I played for about 50 days, hoping for a random one. But the event never started.

This one is a chat event, not a random one.

If this problem still happens, can you come over to Discord and send me your save file so I can check it and try to fix it in game? Sorry for the issue.