Kingdoms of Amalur: Re-Reckoning

This is less a guide and more “tips” for getting this achievement.

I completed the core campaign and the Dead Kel expansion while doing a large percentage of the side quests and tasks (and made sure I succeeded all challenges), but still needed about 15 persuasion successes. After playing some post-campaign side quests in the main game and getting about halfway through The Teeth of Narrows expansion, Wink and a Smile unlocked.

Basic recommendations:
• Abuse the “save” option to succeed the persuasion challenges: save before entering a conversation and if you fail, reload and try again.
• Use the trainers to get four free Persuasion points: Magessa Ohr in Rathir (levels 0-3); Ellova in House of Ballads (levels 0-3); Templar Montainel in Adessa (levels 4-6); and Caradas Hyne in Mel Senshir (levels 7-9)
• Get a free Persuasion point by reading the skill book, available by completing the Adessa Side Quest Paper Trail
• Use the potion Social Grace to temporarily increase you Persuasion skill by three; available from Rhudlyn Rhewani in Rathir
• Max out Persuasion by adding five points while leveling up … the more points you put in, the less chance you’ll need to abuse the save option noted above
• You should first exhaust the conversation options that do not progress the conversation (those on the left side of the option bubble); it seemed some challenges appeared after choosing specific optional comments (I could be wrong here …)

Observations
• Succeeding a persuasion challenge and then reloading the game to try it again does not give credit for multiple successes; you can succeed many times on the same challenge but it will only count as one success
• The game may count successes across different plays-thru but it doesn’t seem to credit you with a success in a subsequent game if you already succeeded on the same persuasion challenge in an earlier play-thru. I only tried this on a single instance and may be wrong. YMMV
• The Teeth of Narrows DLC has a lot of persuasion challenge opportunities and a number of conversations will contain two challenges
• Some conversation options that progress the conversation will result in a persuasion challenge and others will not; if you absolutely need just a few more for the achievement, you may want to run through all conversation options via abusing the save option noted above

The Amalur wiki at https://amalur.fandom.com/wiki/Persuasion_Attempts contains an excellent description for finding quests that have persuasion challenges. I contributed nothing to that wiki.