Don't ever give whiskey to Josef, it is useless.
First of all, progress with Anna until 3 hearts or more before you start giving Josef a Beer on Friday.
Do that 3 times ( 3 Fridays ) and everytime he'll ask you a question that you have to answer:
- 1st Question > How could I forget
- 2nd Question > She's a bit older than me..
- 3rd Question > Anna and I have been making Starmaker Content; Anna let me play with her boobs; If you don't adapt, you'll lose her ( Josef Stays ) or You're a loser, Josef ( Josef Leaves )