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Why didn't you go with him? 

When you don't realize a person is dead and you suffer a severe case of foot-in-mouth disease.
Earl: "I'm such an idiot. I saw our neighbor Mrs. Lundgren at the store today, so I asked her how her husband was doing. I didn't know he was dead. She said 'he's gone' and I thought he was on a trip. So I asked, 'Why didn't you go with him?'"

Opal (horrified): EARL!!!

~ "Pickles" by Brian Crane

Would you like a large fry to go with that shake? 

When you work at a fast food restaurant, if a foxy chick orders a milkshake, you are supposed to ask, "Would you like a large fry to go with that shake?"
"Would you like a large fry to go with that shake?" means "Would you like me to cram my peter into that sexy little body of yours?"

i don't want to go to school today i want to stay home and bake cookies with you 

from the movie Space Jam. Often used by men who are dating women that are no good for them, in circumstances such as Facebook. usually found by the next girlfriend many years later.
(On a guy's facebook page) "I don't want to go to school today I want to stay home and bake cookies with you...(insert skank's name here)".

Will you go out with me? 

For some reason the most terrifying six words (to say) ever.
"Will you go out with me?"
"Yes."

or (and, according to my brain, the most likely situation)

"Will you go out with me?"
"No."

go away or I will replace you with a simple shell script 

Shell scripts don't require salaries and don't complain about yesterdays coffee. You should pay more attention to the creative possibilities of shell scripts, especially in relation to human resources.

the sentence shown here is incorrect. The correct form is:
"Go away or I will replace you with a very small shell script".

go away or I will replace you with a simple shell script 

A semi clever quip made by computer geeks and gurus.. Quite similar to the military quip " You are so fucking useless, I should replace you with a button"