How to progress the storylines for your staff and guests.
Staff progression.
Staff events.

Each event will contain a hint (if you have progression hints enabled) which will show in a tool tip if you hover your mouse pointer over the italicized i. The hints will tell you at which time of the day, location and any requirements that need to be met in order to complete that event which will allow you to move to the next event and earn a reward (change of outfits will get more lewd the further tier progression you make) when you complete that tier and met any requirements to advance to the next tier (such as staff and Manor level).
Guest progression.
Guest events.

Each event will contain a hint (if you have progression hints enabled) which will show in a tool tip if you hover your mouse pointer over the italicized i. The hints will tell you at which time of the day, location and any requirements that need to be met in order to complete that event which will allow you to move to the next event in line.
Enabling progression hints
Make sure “Show hints on progression events” is checked.