Becky the barwench from Oakfield.  I think it may have been me trying to leave the DD via the main exit.  He didn't follow me and my wife out and when I went back and tried to dismiss / follow, nothing happened (over & over again, nothing).  He was stuck at the gate, until I left for a day or two and then he was stuck at the deed

I earned the Homestead by proposing at the Oakfield Demon Door.  I then had a child with my wife.  After completing the Spire quest to get the Hero of Will, I returned and everything was .  My child was 10 yrs old and I opted to take a family trip.  I selected the both of them to follow and walked out the Demon Door to ...