Apologies, I just loaded the save from the route pick for Ashley again and choose blackmail, it didn't glitch this time.
Earlier it got stuck and only unlocked when I reloaded and changed route so I thought that's the reason..
I'm not sure what caused it earlier but basically I couldn't call any girl, and couldn't find anything while "taking a walk". Whenever I went home he would just skip to next day as if nothing happened, couldn't trigger Ava's train incident.
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After further testing (while writing the above text) I managed to do it again, it might be related to scrolling back from the point that event becomes available to be triggered. I have a perfect save file before the error, if u scroll back before going home Ava's event gets lost in the void never to be available again..