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Yes.

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How? Can you please tell me? <3

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I think you need to have your like high enough and then talk to the shopkeeper at night and to visit the barn with him, then you will get a scene in which you can sleep with Caleb. After that the sex with him becomes a random event while entering the barn

SkinnyLegend is right, that's how.

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Thanks guys! But how much like must he have? 

that I'm unsure of.... I just did all his events and the Halloween one a couple times.

20 - 30 like i believe

OK thanks😊

Hey i am sorry for bothering you but I did all the things and I have Caleb on like 58 now but I still can't have sex with him and I am very confused now so can you maybe please give me some advice please?

did you do the night date with bernard? And choose to sleep with both?

Yes

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did you talk with bernard at his night date about Caleb being flirty?