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Basically when you do not know whether you should laugh or cry, so you LOLCRY.
Colin Farrell is staring in the remake of Total Recall?
LOLCRY
LOLCRY by idekcolin July 6, 2011
Words you can keep
v. present 'lolcrying' past 'lolcried'; When one's first reaction is laughter, but upon further reflection sadness or sympathy. Also used as an interjection.
"They made a joke at my expense and I lolcried," or "The Secretary of Education has never worked in a public school - lolcry."
LOLCRY by Ad0nus February 28, 2017
Related Words
The reaction to something that at first appears funny, then reveals itself to also be very sad, or vise versa (e.g. The Darwin Awards)

Can also refer to a reaction to something that is innately funny AND sad (e.g. Forever Alone guy)
Hey did you see those midget clowns punching each other before?

yeah that was hilarious, until one of them died. that made me lolcry

Hey Bill, your life is pretty pathetic! I bet you'll lolcry at this new Forever Alone meme I found!
lolcry by Iamforeveralone May 13, 2011
"Lolcron".

Necron bullshit in Tabletop Warhammer 40k, and in Dawn of War.
"That motherfucker used Lolcrons, didn't he? Welp, there go my Guardsmen."
lolcron by Demither October 7, 2013
A state of uncontrollable laughter, taken from the most popular chat slang term Lol (meaning: laughing out loud) with the suffix -ery at the end, to describe what state of mind you are going through. Also used as a synonym for laughs.
Matt: Hey mark, did you see what I wrote on your facebook last night?

Mark: Oh yeah! Haha that put me in a true state of lolery
Lolery by McVicious July 6, 2009
Laughing Out Loud For Real Y'all.
Britney Spears can sing well... LOLFRY.
LOLFRY by bob ross afro August 4, 2009

lolcrits 

Originates from TF2 and is the response someone gives when killed by a critical hit.

Critical hits are random in TF2 and usually causes one hit kills, prompting players suddenly killed with them to respond with "lolcrits."
1v1 Soldier Fight

Soldier A hits Soldier B twice with rockets
Soldier B fires a critical rocket at soldier A, resulting in an instakill

Soldier A: lolcrits
lolcrits by Cake is not a lie November 14, 2011
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“Did you see that caillou over there? His head is reflecting the sun like a disco ball.”
Example 2:
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scruples; to have manners;

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