Personality wise I am not sure many or even all of the women are interesting outside their looks. Ivy's personality is interesting if one likes bad girls. Jessica is also interesting as the bad girl you might be able to fix, since she is clearly suffering the consequences of her life while Ivy is still reveling in them.
Jessica is what Ivy could be one day, but then again Ivy seems so ambitious that she might not fall down that hole since she seems clever and has some business acumen.
Louise may be annoying but at least she has gone through the same thing Ian has so they have that in common and could potentially be soulmates since he already has a thing for redhead women.
Lena can have an interesting personality if we do not play her completely onesided. Also Holly for those of us liking to "nerd out", her wild version too. She might be slutty, but the nerd is still in her.
Agree with you on Ivy, but as for Jessica, I usually get the nice version with her in a relationship with Dave (as it should be).
If you want stronger personality divergences you must look in other games. Like Dr. Sophia Lundgren, an amoral, eccentric, hot, nerd genius, who also has no problems with gangbangs and black ops medical experimentation on humans. And she is one of the nicer characters in that game, go figure.
The other girls of ORS are relatively generic, Alison is the high school crush you can finally get together with, but a bonus point for her is that she is open to experiment before settling down fully. Cindy is high maintainance, self absorped and while Wade is not innocent about the situation, Cindy is flighty.
Even Gillian, going by their talk, is more selfaware of the big mistake she made by cheating on Ian.
