I had the same issue with "taking care of your ass" not progresssing anymore so i did some research through the code.
The problem seems to be, that the variables "alice.dcv.private.enabled" and "alice.dcv.private.lost" are not set correctly, even if you meet all the needed criteria.
In order to have the talking topic appear when talking to alice, "alice.dcv.private.enabled" needs to be "True" and "alice.dcv.private.lost" needs to greater than 1.
To fix your savegame I'd suggest to setup alice with cigarettes, protect her from punishment and then at 22:00 go to the lounge.
Now before you talk to alice, open the console (shift+o after enabling it through e.g. unren) and set the aforementioned variables to the expected values:
alice.dcv.private.enabled = True
alice.dcv.private.lost = 2
When you talk to Alice now, there should be the option "I was wondering if you're comfortable?"
As far as i checked this has no negative impact on your savegame as those two variables will be set to the correct values after the dialogue.
With this fix you should be able to continue the game.