Here is the full list of all 20 Kathy Rain achievements. It takes around 6-8 hours to unlock all of the achievements on Windows.
Finished the game
Felt no apparent need to let Lenny down gently
Totally mesmerized by Goober's monologues
Amplified Goober's lung cancer
Really had it out for Goober
Engaged in flirtatious behavior on the computer
Learned a cold hard truth about your face
Tortured an imprisoned bum
Rediscovered yourself as a creature of the night
Barely resisted the urge to barbeque a bear
Became a huge fan of those sweet, addictive, not to mention cancer-inducing sticks of tobacco
Finished day four
Finished day three
Felt like literally taking the wheelchair for a spin
Lost track of time on the road
Wanted to engage in a good 'ol book burning
Finished day two
Finished day one
Reunited with a furry friend
Made your best efforts to miss the funeral