Watching out.. keepin an eye out.

Watching behind .. someones watching your back in the 6 O'clock position
Keepin Six is used in jail and in the Military.

In jail it means that your keepin an eye out for the six which is a word used for Correctional Officers.

In the military 6 is the bottom of the clock. Your looking at the 12 o'clock position so the 6 o'clock position is behind you
by C.Ontario August 3, 2008
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A commonly used phrase when seeing a friend, which is immediately followed up with a fist bump. It's a Westchester thing.
Yoo Fino, what good you keepin it tight?
by Joey Pov April 4, 2022
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A phrase coined in the black community that has devolved from behaving with a sense of maturity, integrity, and pride to just acting ignorant and combative at any given time.
Guy 1: "Ey yo son, that cracker gave me a funny look so I punched him in his face."

Guy 2: "But wasn't he interviewing you for a job?"

Guy 1: "Yeaa but I didn't like the way he was lookin me, so I did somethin about it. Keepin it real, son!!!

Guy 2: "Yeah, keepin it real dumb."
by pops87 March 26, 2010
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Staying healthy and on top of your game. 100% in every aspect.
Bob: Whats goin on Johnny?
Johnny: Just keepin it 100, pimpin!
by Andre McCullough January 26, 2007
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1. To be yourself.
2. To be honest with others about your ideas and feelings, regardless of how it may be taken or perceived.
1.Caucasians defining terms that aren't in their cultural vernacular, or realm of understanding, as a way to demean members of another culture or group is a sign of being a racist ass-hat...and that's just "Keepin' it real".
by Keypinitreel May 20, 2009
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A philosophy and identity concept that arouse in hip-hop culture, and followed primarily by African-Americans.

"keepin' it real" is an expression of living only for instant gratification and lack of desire for more. Only the most basic animalistic tendancies are to be acted apon. Lust and anger are the primary emotions. Drinking alcohol and smoking weed are the main hobbies.

Recieving welfare while working as a criminal is one of the few ways to make money while being "real". The other are playing sports such as basketball and football, or working in the entertainment industry.

Jail time is status quo to the point that having never been to jail is mark of weakness in the eyes of those embracing this concept.

The only thing that changes with any certainty is the slang.
Behavior Example:
Showing up to a job interview in baggy ripped pants and a XXXL basketball jersey then complaining the reason he were not hired is discrimination.

Example1:
PersonA: "So are you planning on graduating from high school and attending college?"

BrainwashedYouth: "Hell na, I ain't going to no mafuckin school n shit, I'm keepin' it real!"

Example2:
BrainwashedYouth: "yo nigga whur u be goin?!?"
AfricanAmericanHonorStudent: "Going to class, I have a test in Trigonomery."
BrainwashedYouth: "yo wut u talkin 'bout mufucka? u sposed to be some mufuckin white boy?!?! yo lets mob dis foo!"
*HonorStudent beaten and/or shot*

Example3:
(An African-American man and woman on a first date):

EducatedAfricanAmericanMan: "I have an MBA, own my own home, and have never been to jail."

BrainwashedAfricanAmericanWoman: "Sheet nigga u cant be
my soulja! U aint even really black! I be needin me a man dats keepin' it real!"

by NinjaGuy October 28, 2006
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To reach the boundaries of over-reacting, while maintaining sensibility. "Keepin' it real" should only be brought into action when something personal is being attacked, such as one's manhood, one's mother, one's moral code, etc.

Violence is necessary.
Guy : Bitch, what'd you just say to me?
Woman : I said your mother is an ersatz Harriet Jacobs.
SLAP
Guy : Bitch, I told you to shut your wiki-educated mouth. I'm keepin' it real 24-7.
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