i recently realized something, that in order to get the good ending in the game of the Echo series you often need to give your love interest what they NEED not what they WANT. spoliers for Carl,Leo,Jenna and William's route:
in Carl's route you need to turn down Carl's ideia of letting James I posses him
in Leo's route you have to tell Leo that things between them are over
in Jenna's you have to disagreed with her cynic statements at least once
in William's route you need to take Nik's side over William's in the issue of the bridge
now this next part is speculation, i believe that the wrong choise when comforting William after he finds out his wife and son are in town is to tell him you think his duty to his family is noble because you are basically telling him that stayng in the closet and marring and having a family with a woman you don't love for no other reason aside that it is what society expects of him makes him vituous and i think this will lead him to choose his family over Samuel down the line
after you get out of the cave , i think telling William that theres nothing wrong with him is the wrong choise, not only is the only choise where you don't take the group picture but looking at the other options they are all about telling William not to trust his senses, in Murdoch 's route Murdoch and Ralph tell us that William is vey logical and trust his senses and that this will lead him to get to the wrong conclusions which is what i belive this choise is about