That's what gets me about the writing in this game. Typically I can't stand the blonde sporty/cheery types, and when I saw the initial renders my brain said "Oh, hell no, move along." Then I got into playing it and damn if she isn't great (and Derek is a fucking riot, I love that insane dude). For my particular tastes, Sage is too mental to be taken seriously. Jill feels like a sex doll(it's the look, I haven't played down her actual path yet). Quinn IS a sexbot (and heroin addict from the looks of things). I suspect most of the girls working for her just fall into the 'bad idea' category, even though Camila is pretty tasty looking.
I just don't know what it is. I'm not really a Josy fan, in the same way I just wasn't keen on Megan in Acting Lessons (though I absolutely adored Melissa), so that means I'm looking at Maya or Bella for a serious playthrough. Maya seems like a legitimately good person to me (even if she doesn't want to come out of the closet), and her brother being awesome means a good relationship likelihood there. Bella is a lot more serious(whatever her reasons), and feels like she's more inclined to really commit herself once you've shown you're not just a sex-starved poonhound.
In the purely "senseless debauchery" side of things, a Camila/Maya tag-team would be my first pick (unless Jade wants to join in that combo), but I think it'd be fun to ambush the D&D nerd girl with Lily or Riona as well. The idea of Magnar kicking MC's ass for bedding her makes me giggle.