So the way I got winter was by having my answers logical, avoiding the approaching clipboard person, night, and staying calm under pressure. But the way the game describes it as, "the coolest people around, never the type to be ruffled or influenced. Calm, but straightforward observers. They may be quiet, don't mistake that for passivity: they're observing and won't hesitate to call people out, even at risk for their feelings." So choose your answers based on this!
Hope this was helpful!<3