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
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?
