In addition to this, I'll suggest calling Shiori into your office and then talking with her. I've sometimes been able to trigger a story convo that way when it wouldn't happen otherwise.Last steps are discovering she has debt, talking with the manager and repaying said debt, then talk with Shiori about debt. It might still be bugged since someone screwed her file pretty badly in this last update and the last 3 bugfixes supposedly didn't fix everything. So, wait a while, go to work, try to talk to her both at and outside work and see if the extra option is under talk or not. If it's not there at all, wait for a fix.