I’ve tried everything, but I cannot seem to be able to get the You Had One Job achievement. I’ve tried different dialogue combinations, I’ve tried starting the dialogue already drunk, different combinations of perks, etc. The only time I actually managed to drink myself to oblivion was when I started the conversation sober and then drank some more when I was supposed to be taking Ambrose’s money. However, this didn’t award the achievement. Whenever I tried and I logically should have passed out way sooner, I simply start drunk at the table with passed out Ambrose, my drunkenness indicator is completely full, but I don’t pass out (even if I drink more alcohol at that point).
It´s not a bug. It depends on your drinking skill and your drinking perks.
If you have wine biber, it helps to get the archievement.
Wine biber = beer is 50% stronger.
Drinking Skill 9 or lower should work.
If your drinking skill is too high, you won´t drink to oblivion… (you will need another save file for this archievement)