Incoming!
Actually, after laying down 10s of pages of arguments on how the writing is crap and basically all the characters exist to serve evakiss's cheating bully fetish, I finally realized what I was doing wrong.
I had never taken the Alison true love path.
Ignoring the 2 doller strumpet Lena, playing Ian to find true love in Alison was the most fun I've had yet in this game, not getting dragged down by cindy/lena/ivy and their gutterfolk shenanigans, it's extremely enjoyable as a pure dating sim. Alison is by far the best LI, and comes free of all the baggage the rest of the cast is swimming in. (except for Holly)
-edit: everyone talking about how technical the fight was, it seemed like a snooze if you went to the gym regularly and stuck with jiu-jitsu.