Here's the quick and dirty guide:
Challenge 1: David Madsen
If you confronted Madsen when he was confronting Kate, you automatically pass this, and can say anything.
If you took the photograph, there are four conversation options. The only one that will pass the conversation is to tell her "I was scared."

This is factually incorrect. A player who has taken every possible supporting option to save Kate still stands a significant chance of watching her take a headfirst dive off the roof, whilst one who has always refrained from taking the "supportive" action can still walk her off the roof if they make the correct…