Ord.

Choose Dimensions

Dimensions has three different worlds you can travel between: Desert, Groundhog Day, and Jungle. Upon waking up you will get the option for Portal, which will have an RNG option each run of the game. Roars will take you to the Jungle, and Wind will bring you to the Desert. At some point within Desert or Jungle you will get an option for Portal again, which will take you to the Groundhog Day Dimension.

After entering the Desert, the RNG will eventually give you the option to enter The City and later on the Sewers. Upon going down into the sewers, do this:
Approach
Personality or Style, it doesn't matter which
Bow
Find
Steal
Yes
Take
Leave
Follow
Hide
Watch
Follow
Shoot twice in a row
Beeping
Drop
Open

Go through the rest of the options, choosing whatever you want until you get the achievement.