Anna and Adrian one was a bit of a trial and error for me too. I just went through all 3 options one each Friday, I think the last option "seems like you have a question" was the one to progress it for me but it possibly could be that you need to run the progression where pption 1 makes him jizz in his pants, then 2nd option you and Anna fuck in front of him, and then option 3 is when he gets into it.