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(+3)

What are the flags for Gale accepting the necklace deal? I triggered it on my first readthrough but he was unphased on my second.

(+2)

It depends on whether or not your MC uses magic as their primary weapon (lowers the chance), whether they offed the thug in the prologue (lowers the chance), whether they got ambushed by the trio or walked up to them on their own terms and on the MC's responses to the questions asked. The more info they reveal, the higher the chance, up to you.