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At the old barn or at Bernard's house? 

bernards house.

How can I sleep with Caleb and Bernard in his house? 

You go to bernards house and ask to go to the barn with him, not in his house sorry.

I did that and now? Oh and other question why can't I do more houses that Bernard says the one where I can build the fair and watchmen but I can't build more houses

what? Which version are you on?

0.25

that explains things. You can't do this event in that version, you gotta update to 0.27 to unlock this event and to be able to do this.