It's almost impossible to not talk to anyone in front of Kylie before meeting Ayesha in the gym and kissing her.
While I certainly respect your enthusiasm in regards to chatting with the pretty girls in the face of mortal danger, I can tell you that Kylie's stabby meter only fills up when you actively interact with the ladies via the buttons. The random hello/event that can trigger when you walk into an area usually doesn't count. So that's not the tricky part.
Fun fact that's not really mentioned in the wiki: Trying to friendzone Kylie will give you the 25 Yandere points you need for the harem. This would be the safest way to get them in this regard ('safe' being a relative term considering it's Kylie), so you can focus on raising her Sub points.
Also, are you sure you got all the prereqs to start the Harem? In my last run I found myself wondering why it wasn't triggering, before realizing I had completely forgotten to have sex with Ayesha...