I'm having trouble with getting past Zarad's stargazing date.
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To pass the check with Avalie and get his date, you need at least 35 insight (which should be quite doable from meeting all the delegates on the first night) and 25 people. I'm not sure if it's possible to pass unless you took a background that gives +People (like the Revaire widow) or chose a bonus to People in character creation!