Okay I'm officially lost on how to get that first ending haha. Anyone willing to give me a hint?
It's the roughest ending, and you get it if Chloe has so little confidence in you that you skip right past the first choice of recommendations, then make the joke about rubbing one out.
So it's pretty hard to get by accident! Qmin is too good at her job. That specific option is perfectly fine if Chloe is already comfortable around you, but it's the straw that breaks the camel's back if she isn't!