After the event with Tifa triggers in the town square, go there again while tracking Blaine's route, and the date should continue.
Viewing post in Blaine Date Softlock
Yeah I think I got it. The quest was completely gone, I couldn't track it but after trying a bunch of different things I managed to get the adventurers guild quest to progress, and upon returning to the town square the date continued. I'm not telling you how to make your game, but I think the whole quest tracking system needs to be polished up a bit more. Either no quest should progress while not tracked or you should sort out a sort of priority system for events so things play out smoothly. Having to track and untrack quests to figure out which one it's trying to progress and locking everything else up until you find it is really not great.