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2.
A way of asking a woman out on a date....not to be your girlfriend....on a DATE!
Joe: Will you go out with me?
Jane: Sure! Movies at 7?
Joe: Sounds great
by smartiiiiiiiipants December 30, 2010
 
1.
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."
by The Second Dictionary Man December 13, 2013