somethings I think are a glitch like rogue always getting embarrassed and running off, others I think are actually tied to either her level or a hidden stat like reputation, orgasms, level. all you can do is be as risky as possible at that point, eventually it sorts itself out.
In my case, Rogue's stats are all maxed out, and otherwise she is willing to run around nude all of the time. I discovered it right after I learned that they could have a three-way, so had assumed it was part of that, and was disappointed that Rogue did not have the option to take Kitty's clothing off too. ...Then I tried it, and it ruined my nice evening's plans. lol
Speaking of bugs, I was glancing through the code, and noticed that there are plans for a real detention, which might be a new room, as well as stuff for Emma's bedroom, etc.