I've been thinking there could be some really interesting possibilities in a game with a format like Whoremaster (or Sim Brothel, etc), but where the player is just trying to date or hook up with girls. There are plenty of "sim dating" games like this, where the guy has to build up his stats and put in the time so the girl will like him, but it's always just about pursuing a specific girl (or a couple girls) with a predefined time limit. So it really becomes a "beat the clock" challenge, with time management being the core of the strategy, and no replayability once you've got to the end with each girl.
To my knowledge, there aren't any dating games in the Whoremaster format where you can go as long as you want with a potentially endless supply of girls. Of course, the drawback to this type of format is that there wouldn't be scripted events, and the visualizations of each girl would be limited to what you could plug in; but it would also have more dynamism, and wouldn't rely so much on the time-management factor.
Now, don't get me wrong, I really like Whoremaster. A lot of the elements germane to the slave/brothel setting appeal to me, but there are also times when I'm interested in a more tender romantic setting. So why can't we have both?
Does anyone know of anything like this? And if not, how hard would it be to make? Would it be possible to mod an existing engine into something like that, or would it have to be built from scratch? Would anyone else be interested in playing a game like this, or is it just me?