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Have you updated to the latest version 0.5.0l? I've had the same issue but after updating from 0.5.0h to 0.5.0j it hasn't happened.

You have to finish their questline to unlock the option to date them. Go to Hints and see what you have to do next to progress it.

Don't worry about the friend status! They will still play the role of your admirer, just now they're also your friend so the labels in their profile change accordingly. You can still date them no problem.  I'm not sure as to why their storyline isn't triggering for you though but it's definitely not affected by becoming friends. I agreed to being friends with them and wasn't locked out of their storyline. They also recently asked my MC to be exclusive so you don't need to worry about that locking you out of their romance either. It might honestly just be unfortunate rng 😅 I hope their storyline scenes will trigger for you soon!

I've gone on 9 dates with The Classroom Admirer but the Date Card with dating milestones doesn't show up in their profile. Does it only show up once you finish their entire questline? Or is it perhaps a bug?

An error has occurred. You may be able to continue, but some parts may not work properly.

Error [PassageReady]: <<set>>: bad evaluation: TypeError: pdata.nightlife is undefined 1.

^I'm getting the error above in random moments in the evening. I got it first when I was out in the town when the hour progressed from 5PM to 6PM (no matter what I was doing, if I was working at QuickieBurger or playing a game at the arcade, got the error all the same). Then I reloaded before the error happened, went back into campus until it became 6PM, returned to the city and the error didn't occur this day anymore. However the very next day after 8PM I exited my dorm and tried to enter the Summit Market, and got the same error.

This is slightly concerning because my playthrough has become a balancing act of reloading and trying to avoid triggering this error so that my save doesn't become corrupted x.x At this point I really hope that it's an easily fixable coding error, and not my save having something glitched out with it ;-;

I really love how everything is written in this game. I don't know how to describe it. It just reads so easily, it's not too cluttered with descriptions, and the emotional scenes hit so well. Every character feels so alive and unique (even the randomly generated ones), they have their own interests, opinions and things they find attractive. One thing that I would like to see, if I could make one request, is descriptions of what skill points each uni class provides in course selection. It would be really useful, especially when planning to do a new run with a specific kind of MC, since the skill points you get from daily classes help out a lot.