I am going to once again note that that conversation is the worst implementation of skill rolls in dialogue in the game so far. That should dialogue tree puzzle. The skill roll should be a short cut at best and setback at worst. The girl's fate should not be determined a single die roll.
Having just a dialogue tree negates any skill the character is supposed to have. We can choose the approach (e.g aggressive, compassionate, etc) but skill should determine how effective we are with that approach. And the way to gauge that is with a roll.
The OP point, I need to pay more attention. I have tried Guidance, but I don't recall any benefit.
