Popularized by the movie, "The Heathers", this phrase is said in response to a request one deems impossible or absurd (much like being gently fucked with a chainsaw). It's basically a way of showing someone how ridiculous what they've just asked sounds.

Ex.
Veronica: “Why can’t we talk to other kinds of people?”
Heather Chandler: “Fuck me gently with a chainsaw. Do I look like Mother Theresa?”
Dylan: "Hey Nick can I borrow your car once its out of the shop?"
"Fuck me gently with a chainsaw. You crashed it just last week!"
by Cotbumm July 22, 2016
A quote from the movie Heathers
Also a random phrase to say if ya dun fucked up, wanna be fucked with chainsaws, or if you just feel like saying some weird ass phrase.
Fuck me gently with a chainsaw! Do I look like Mother Teresa?!
by do-you-even-hansen January 31, 2018
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
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
"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
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