For anyone that wants to try editing their save if they missed the Jane/Jess massage, i fixed my save by changing to 1 the following:
JSON:
JaneJessMassageHappened #981 :(0)
JaneJessGoodEnding #989 :(0)
If they are already 1, then this isn't the issue for your save.
Edit: looks like it didn't fix it well enough. I got to the point I should be going shopping for an outfit with Jane ( This Time You Get New Clothes event), and at lunch I can ask her about the the date with her and Jessica (she says not yet, because they have to get new clothes for the MC), but at the end of the lunch she just up and goes, no shopping happens. I don't know what else to try..
Also, anyone knows what the 'afternoon fun' event is with Joan?