Spoiler alert. Do not look ahead if you do not want a walkthrough for every medal.
Burn baby burn: Take a shower
Cereal killer: Eat the peanut cereal
DERP: Type words that the program does not understand about 3-4 times. (You can just write random letters, like enuifneibf.)
Have a nice trip: Put on the dress in the closet, then attempt to grab the hanger.
Oh poop: Type poop.
Oh poop II: Go to the bathroom and type toilet.
Oh poop III: Put your dress in the unflushed toilet
Poop princess: Get all 3 oh poop medals.
Road kill: Get to the part where you choose to sit in the front or back seat. Pick the back.
Suicide: Do i even need to explain this one?
Going viral: Use the computer
Partying, partying NO: When you get to the front seat back seat thing, say go inside.
Winaholic: Find all good endings. Going viral, partying partying, yeah, and Partying partying no.
Secret: Get every medal.