I've come across something of an issue, maybe a bug?
Jessie's date at her apartment, it conflicted with a mandatory story date so I had to miss it. Afterwards, I am completely unable to resume that date with Jessie. I've raised her lust back up a good amount, but is there a certain threshold you must reach?
The problem is that two events got tangled up... :( the new version has a security measure so that doesn't happen, possibly your game already had the events tangled up and it's not possible to separate them, I suggest you start a new game, if you want, I can send you a saved game so you don't have to start from scratch.