Offer him comfort (Diamond)
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From: The Shepherd's Wash
You made a similar choice once, in the alternate.
Unlocked with An Invitation to Sing in the High Places exactly 2, A Kitten-Sized Diamond, Liberated from the Mountain
Success
A diamond in the claw
The Forlorn Shepherd says nothing as you recount your dealings with Fires; of the surrender in its office, of all you have bought since. Coin can be both chain and freedom.
"We are what we have done," [...] "And all that we could have done, and did not."- The Shepherd has a request. (Sets An Invitation to Sing in the High Places to 5 - A moment with the Forlorn Shepherd)