So the event call will be assistantNekoWork and that an already thrown flag will show fail or success and events will handle from there. The event system them matches up checks if it was a success or fail and moves on.
As a side note for the odds of success would you like happy face, sad face, neutral face or just percentages?
You can talk to your assistant now. Event System handled.
Adding new assistants should be easy though it will always be the first 4 who are the default "lover" assistant. Assistants will still have tons of flavor and this should actually get more and more detailed.