Having the issue on A New Journey where it says I need 10% intimacy with a character from school, and I do, and it just says I need to sleep. It doesn't seem to be progressing at this point.
Sorry guys ;-; 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 ^^