It's interesting, because for me, Cherry is, probably, the only true waifu in the game. I mean this game obviously pushes MC toward Lena, Holly or Alison in the terms of girls you can form a true bond without being a jerk towards your friends, but... Holly NEEDS protection and love she can get only from Ian and Lena and, well, those shy girls are great IRL but in porn game? Not so much, couse I want to fuck around without feeling like shit. So Lena and Holly are a couple in my game. And maintaining a relationship with Alison just woudln't let you fuck around to begin with. I don't even mind her sleeping with Jeremy, but she basically rushes him every second MC is not around and that is just unsetteling.
Then there are Cindy and Emma, but Cinders is shallow as fuck and you are cucking your friend in the process. Bad foundation for a relationship. Emma is great, but she is Perry's dream girl and have feelings for him so you can fuck her, but, in the end, she will probably pursue him.
Minerva is sexy as hell but married, Louise is nonexistent in Ian's game, Ivy isn't for serious relationships and Gillian is for cuck connoseurs only. That only lives Cherry. She is sexy, smart, she makes art... You can bond with her and fuck around.