You have to befriend Adrian, there may be a bug with older saves preventing the option so you might have to start over
does befriending means taking the share anna route with adrian? or what i dont understand
I personally did the sharing route and it triggered for me after I came back from a Hiking Trip. Unsure about non-sharing though.
No, it just means spending time with him, like playing games and generally being nice to him, no Anna sharing required.
