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Sounds like your game is broken.

Is there a certain day that the event was supposed to occur. After the cabin where the BDay was talked about is when I went to the High Elves, is it possible that her event was supposed to take place while I was gone therefore it won't be able to be progressed?

No, all events are on a timer between 2 - 4 days in most cases. Then the other requirements must be met. For Ashley's birthday, all the main characters must be available.