So I just played this for the first time, and I have to say - I love it. There's a real feeling of accomplishment in gaining enough favor while trying to decide what you can give up.
I have to say, though, that if it weren't for the checkpoint system that I notice was just added... I'd probably be silently screaming after carelessly botching something. It's a real lifesaver. If I might make a suggestion, however; maybe Evette's first naked lesson should be moved to after the checkpoint? As it stands, that event decides who's going to be the dominant partner in their relationship; it seems a bit more consequential than the rest of the checks, which just change affection or favor. If memory serves, it should only change things by one week.
Also, it might be nice to add a checkpoint at the very start. I realize that sounds superfluous, but there were a few times (okay, maybe more than a few times) where I thought that the meeting lineup looked perfect, only for me to make a careless math error that lead me to restart, and left me kind of disappointed to have wasted such an opportunity.