There seems to be a bug that places you in an untyped timeslot after you complete the christmas event. During this time none of the characters are in any of the rooms. This also seemed to create some weird side effects. My process was as follows:
1. Set up a date night(not the first one).
2.  Do the date night.
3. Click on the Present.

4. "Get Present".
5. Leave Event room.
//At this point it was strange because it was night after the date but steps 3-5 made it seem like day but there was no indication of timeslot.
6. Navigate to kitchen.
7. Do Dishes. //At this point it becomes morning and the appropriate characters load in.

8. Setup Date Night.//At this point she says that you already set up a date night.
9. Wait til Night.
10. Navigate to Dining Room. //I stop here because She is not there to do date night but the room is set up as if there would be date night.