Optional Conversation #35: Once you enter Avery’s entertainment room, a conversation with Elena will trigger.
Optional Conversation #15: After reaching the second floor of the tavern in the marketplace, approach the chairs to trigger an optional conversation.
Optional Conversation #16: Interact with the cutlass that is inside the Blacksmith’s building to trigger a conversation with Sam about trading.
Optional Conversation #4: This optional conversation can be nabbed by interacting with Sam right after rappelling down from the window and swinging across an archway.