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I just wanted to ask why don't the dates work for me? After my first date with Toshiyuki I couldn't date him because of some error occurrances when I tried to pick clothes, I restarted the game multiple times and it didn't help. (Btw I love this game very much!)

It happened the same to me. In my second date with Toru when I picked the regular t-shirt, the game stopped because of an error. I closed it, reload my last save and chose the trousers first and the game didn't crash anymore. 

I chose the trousers (as you did) and it worked, so thank you very much! :D