Here is the full list of all 26 Dialogue Box: The Road Less Traveled achievements.
Found the drawing of what may or may not be a cat
Picked a flower
Found an empty envelope that was used to hold evidence
Found a phone with an incomprehensible conversation between a stego and his father
Found a board game that was left incomplete, D20 included
Found a globe with significant inaccuracies, and a couple of bell peppers
Found a crate with colorful marking that needs to be seen in a different light
Found an arrow that should not be shot at a living creature
Found a Christmas gift that was never delivered, perhaps for the best
Found a fish out of water (like, wayyyy out of water)
Found an uncomfortable, ugly couch
Found a glass that used to contain soda and sadness
Found a conveyor belt that did not convey its purpose
Picked non of the flowers
Went through the dog house
Went through the broken fence
Jumped above the dog house
Crossed the canyon through the bridge
Crossed the canyon using the cable cart
Crossed the canyon by flying
Have a short name
Have a long name
Your name is Jeff
Get the dog near the tree
Get the cat down from the tree
Wait for the badger to come out