Okay, I took a look at your save, for someone who tried to make out he didn't know what I was talking about when I mentioned the flag console, you seem to have been in there a lot.
I have just counted 126 alterations to your save, so you do know what the flag console is, as when you alter a flag through it gets stored on your save file.
The reason the date won't trigger is that you have altered so many flags your save is bugged, so no matter what you do the date with Ashley wont trigger, here's an example of your save with mine can you see the difference ypou have to start again or go to the save game thread and get a save fron there sorry I can't help
Your Save
View attachment 394787
My save
View attachment 394788
So you can see an obvious difference, this also tells me you have been in there without having to look at the logs.
Sorry you must start again as your save is useless