if you really can't and don't want to make a new game, you can edit your save to make anna seduce adrian. the rid of this event is 2265, you simply replace "false" by "true" at this line 
if you try this: you should have 2 line where rid 2265 appear unless you have more than one save (ctrl+f and write 2265) [you can open the save with notepad/i use VScode in screenshoot but they do the same thing] (all saves are stored in the same file in order, the first time one line appear it's save1 if the exact same line appear later it's save2)
after looking at your reply i tried opening the file GameCreator.Runtime.Core
and other files that had game creator in its name but all of them were saying null and some other stuff
could you please explain what i need to do i have already created 5 new game saves to complete adrians quest line yet i always face the same issue
i may not be correct but in 1.4A the latest version you can go for a vacation to different places at the end of the week it always gives you an option when you try to end the day on friday and friday only .
there is the option of going to japan so im guessing by giving him money and then choosing to go to japan you can bring him along , i dont know about anna being with them at japan maybe she is there dk.
I personally never gave money to adrian for his trip to japan (even the variable for this in my save is on false) and i can go to japan just fine. I did told him to stay and chose the sharing route with anna, so if setting [rid 2013] "adrian-will-stay-start" on true didn't work you can check my first post on this topic about [rid 2265] "anna-will-seduce-adrian" just to be sure it also on true
