There is a bug were after first date with Brymror the game say's there is no more content for this character in this version
When are you trying to date him again? You can only access the second date when prompted during on Day 8 when you are in the bar with him.
Yes, immediately after his first date
It's working as intended. But I can take that as feedback that it seems unintuitive that you need to wait for a certain date.
Baku
