So you finished everything mentioned in step 3 of his female events, and step 4 is not triggering? https://renryuu.miraheze.org/wiki/Grey
If that is the case, can you send me the .rpgsave file from the www/save folder with the number of the save slot in which you have the issue to Naughty-Netherpunch@web.de so that I can take a look at it?