This achievement is earned during Wyatt's chapter of the game. A few minutes into the chapter your friend will suggest playing rock, paper, scissors to resolve a dispute. Select "Okay, that's fair" to play. Win two out of three and the achievement will unlock. If you lose two, quit to menu before it auto-saves and resume the game to try again. The pattern at which he goes seems to be random. Here is a video to go into a bit more detail for it:
NOTE: If you've already missed this achievement, rewind or start a new game on Wyatt's chapter. Rewinding will cause you to lose progress you've already made.