You have to get his relationship high enough and have certain events with him done, Like sleeping in the same bed at the cabin and a having a drink with him. (Not in that order drinks are first in the event list)
How to get to sleep with him on the same bed?
I think you need one or two hearts with him.
It only goes to 100 and after that no heart:(
Did you do his event before the shack? Like the drinks?
yes
