First used (?) in "Heathers" http://imdb.com/title/tt0097493/ , probably more close to meaning "well, I'll be damned" or "Well, kiss my ass".
Heather Chandler: Well, fuck me gently with a chainsaw. Do I look like Mother Theresa?
by OldFart77 December 12, 2006
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a sarcastic term implying "what a load of crap"
or, "bullshit". can also be used as a expression of anger.
: hilary, i did NOT have sex with that woman...
: um... fuck me gently with a chainsaw, bill.

or...

: how was that test?
: fuck me gently with a chainsaw, mike.
by Qwerty April 20, 2004
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west texas chainsaw

The act of ripping anal beads out of someones ass as though you are starting a chainsaw
Hey Nikki have you ever been west Texas chainsawed
by Sick kackis August 27, 2021
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"it's just heather, why can't we talk to different kinds of people?"

"fuck me gently with a chainsaw, do i look like mother teresa? if i did, i probably wouldn't mind talking to the geek squad"
by heathersssssss April 19, 2010
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an expression used when something wrong has happened, or hasnt turned out well ; much like "oh fuck me"
Jessica - "Oh hey did you do that chemistry homework?"
Stokez - "No, but it's due tomorrow, right?"
Jessica - "No! It's due today!"
Stokez - "Oh well fuck me in the ass with a chainsaw!"
by Stokez November 18, 2007
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like a chainsaw to my sack

A phrase vocalized when in a situation of extreme disappointment
Bro, that's like a chainsaw to my sack
by Ed from Good Burger January 31, 2020
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a phrase for "i hate my life" or simaraly, "fuck my life" popularized by the eighties cult classic movie "Heathers" starting Winona Ryder.
"you want me to go talk to those losers? fuck me gently with a chainsaw."
by kdrrrgs July 22, 2008
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