Silver-Tongued DevilWon 50 Speech Challenges - 20G
By accident, I discovered that Pappy in Big Town will allow you to perform the same speech challenge over and over assuming you don't fail. So ask him "You came here with Bittercup, right?" until you reach 50 challenges then stop talking and do it one last time to unlock the achievement, this because it is a glitch and I found myself at 62 challenges before I realised that the game only recognises one speech challenge per dialogue.
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