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What you have to do is get to 10 love with any character that appear at school After reaching that level, you will be able to revisit the hospital and repeat the scene and you will be able to ask for advice to improve your interaction with the characters and you will also have access to the jobs 

Sorry. That's a bug ;-; I fixed it in version 0.23.

As a temporary solution, you can try to increase the intimacy point with another character instead of the girl with red glasses (WDIS), she's probably the one with a bug on the checking code :v

Class president (WPRE) and pervert dude (HPRV) should be the safest try (I guess), but others may work too (I guess).

Consider joinning our discord and sending me a message there if you need ^^