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I found it easiest to do this in a pure run after you have completed the game, you find an enemy that already has a red name and give him a first time (any will do), then you can go and fight some battles after and he will inevitably show up, you defeat him and bag the achievement.
Hope this helps, if you have any other questions I spent an unreasonable amount of time playing this gave (because it is totally worth it lol poggers game) and have an okay grasp on most of its mechanics and can probably answer other questions! happy hunting