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Hm... is there any option when clicking on the bed to "Hire a new maid"?
That should lead to hiring Iris, which basically starts the 2nd chapter.

Are you playing on PC? It would be great if you could upload the savegame + persistent file from the savegame folder (use workupload.com, or visit our discord), then I could check the variables if there's actually a bug or just an unclear story hint.

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It's the Android version. It's working now. It may have been that I didn't do the second time around on Emily's dungeon event being restrained by Leyla. After doing that again, and setting Emily as my alarm clock, I suddenly have an option on the bed that says "Take a walk with everyone (ends Chapter 1)".

Alright, glad it's working now :)
Though the "Take a walk" option really only depends on reaching a certain Relationship value with everyone, and the time of day.
If the relationship values were high enough for all 4 maids, the time of day should be the only factor whether the option shows up or not.
But I'll check the code, just in case.