At the moment, the available options don't change based on what routine is active; I'll change that in an upcoming release. In my testing, once you do choose, "You can pick the menu," you should get breakfast with Terry the next morning. I'll keep investigating to see what's going on! If you're willing and able, it would help me diagnose it if you send an affected save file to phanes@phanes.me (on Windows, save files are stored at: %APPDATA%\RenPy\RuinMe-1537207983 ). Either way, I'll try and track down what's going on!