You need to have completed these steps:
- Bareshade's lewd fame at least 6
- Morale camp at least 25
- Had sex with Barrel at Bareshade's tavern (he is there if the morale camp is at least 25)
- You have a house in Bareshade
- Choose the option "sleep 8 hours"
For the wrestling event you can see the steps in the new post on "development log"