I really love this game. I'm not a graphic novel player but I really enjoy the letter mechanics. I couldn't figure out how to process after I said something like "I can only pass with a successful date", she kept walking away from me :(
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Thank you very much! I am so glad a lot of peopme seem to like the letter mechanics!
The way to progress might be a bit... counter intuitive. There is one alternate way your date leaves, by being pulled into a crack you created.
If you haven't seen one of them the key might be being silent every now and then (gor example, after asking about the succesful date, try staying silent) These "cracks" persist through the loops so you just need 3 unique ones. Good luck!