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With Harold, is there supposed to be something that tells me I have Belly fun? It's frustrating because all I want is sex in my house with Barrel. I can't even talk to Barrel at the tavern any more, there's no option to go to him

For "Check on what the thug is up to" option, you need to have a love potion in your inventory. And another requirement is the same, you need to play in the green route of Northcrest conspiracy. And for Belly fun, if you sure you have all requirements met, it should be show in talk option like here.

I'm 100% sure I have all the requirements met. Next time I go on, I'll grab three screenshots to show you just how weird it is. 

I'm trying to just get the option with the wrestling with Barrel. He shows up and there's 2 options - fair fight and throw the fight. No matter what I pick, he never shows up at my house in bareshade.


All three things needed for Belly Fun to show up, and nothing.

May I ask, are you play this game in PC or Android?

PC

Have you try playing my save files? It should work normally with my save files.