The only one of those conversations that has a true dialog choice is the swimsuit one.
The walkthrough says to pick the nice entry.
However...
I was just going through day 6 again to confirm my above statement, and something different happened.
Normally she gets drunk on the ground by the couch first. This time she was asleep in the room first. When I went to finger her, it actually had an animation. Normally she starts to wake up just as I touch her.
And when the next morning rolled around, she asked me both questions.
View attachment 3264411
So the trigger appears to be the fingering animation event.
I am guessing the first "Is she in bed?" event is slightly buggy.