What was the last scene? Have you taken him to a hotel after he's drunk?
Then you'll have to keep working at the pub. His schedule isn't fixed, and sometimes he comes after 2 weeks. I usually see him on Sat but might not be the same for everyone. October is rather late though, you'll have to have that last scene of him not appearing at the pub anymore before December or it won't work.
You may have to redo his events with at least the superstar and money cheats so you dun have to worry about auditions and money and concentrate on Kaede's routes instead.