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Message: <blockquote data-quote="James McMurray" data-source="post: 4325804" data-attributes="member: 743">For the record, the social challenge was one of the samples in the DMG, with DCs that match our level. We'd probably have done better, but the DMG describes using Insight to "empathize" with the other person. I and the other player with high Insight heard that as being empathetic towards him instead of reading him and using that information to steer your conversation. I managed to bomb my Insight checks, and the other PC (the cleric of Pelor) chose to use his lower Diplomacy instead, because he didn't want to be nice to this guy (who was fairly obviously scum). Had he been using Insight the whole time, we might have made it through, although it's still doubtful because our skills weren't oriented to the task.The GM later explained our mistake, and we'll know next time. My mercenary heart won't have to be squeamish about being nice to people, and the cleric won't have to be nice to dirt. <img src="https://cdn.jsdelivr.net/joypixels/assets/8.0/png/unicode/64/1f642.png" class="smilie smilie--emoji" loading="lazy" width="64" height="64" alt=":)" title="Smile    :)"  data-smilie="1"data-shortname=":)" /></blockquote>