|Danced with the same character at least 20 times.|
You may get this while going through Story and Master Quest, but you can also just keep choosing the same character for performance mode. Once you reach 20 songs, this will unlock. 20 songs is also the longest setlist you can create, so you can get this by creating a 20 song setlist. You will probably get this naturally while grinding moves even if you are not trying.
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