Term used in the military or government to describe being near a headquarters. The flagpole is often located near this building. Its not someplace most people want to be since it usually involves political infighting, following all rules to the letter and bureaucratic drudgery.

This can even mean working in a different building some distance away but the common thought is that the closer you physically are, the worse it can be.
I've been goofing off way out here but they're moving me close to the flagpole.
by sfmc98 September 30, 2009
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The act of taking a hockey stick and thrusting it up another individual's anus.
"listen Jared, if you don't shut up i'm going to turn you into a Canadian Flagpole."
by GLHM November 29, 2011
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A guy lays down with a full erection. The partner then commences to sit on said erection, rip off her shirt, and wave it around like a flag in a strong thunderstorm
My woman and I did a Florida flagpole last night, funny thing is, we were actually outside in a strong thunderstorm.
by Rpveeham July 26, 2014
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A hanging wedgie, executed on a flagpole instead of any other object.
I was in the classroom and the teacher had to leave for 5 minutes. We were all sitting there and the girl bully saw my undies sticking out of my pants. She yelled TIGHTY WHITIES. Everyone Jumped at me and stripped me down to completely nothing but White strong tighty whities. They then dragged me by my underwear to the school's flagpole and attached them to the pull string. Then they pulled me all to the top and I Was sky high on a flagpole hanging wedgie. I cried because girls and everyone saw me up there naked only in briefs. I was often fed by the girl bullies but then raised back up. It sucked! I pooped and pissed by underwear like 10 times in 1 minute. 2 Weeks later though a MILF teacher saw me and got me down. I needed counseling. Hanging wedgie nerd is what I am.. A flagpole wedgie..
by Liam72 March 26, 2014
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1. The Greatest Musicians to ever live.
2. Spreaders of Antarctican Propaganda.
3. A large penis.
1. Matthew J Nerger III, Alexander Elijah Hampe IX, Derek Abraham Ray IV, Peter Moses Murphy XXVII are in Citizen Flagpole
2. "Have you heard of color? And how!"
3. See #1's pants.
by Jesus Christ XIV May 7, 2008
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What happens to a penis-havers' brain after said penis has been accepted and allowed inside another person (orifice doesn't matter). The penis-haver then feels that they have rights and privileges to criticize various things about the penis-receiver opinions and life-choices.

Also, can describe any man that is hopelessly unable to stop mansplaining even after they've been spoken to repeatedly and at length, even with reciprocated understanding, to cease that kind of bullshit.
Sarah was having a pretty good day even with constant line of customers, until this one guy with apparent Flagpole Syndrome came in and told her how the espresso machine worked. She was rightly frustrated because Sarah has been a barista for the entire 6 years she has owned the coffee shop - especially because she used to date the guy.
by KrampyDoo April 19, 2017
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I was dreaming about jen and Melanie at the lake and I woke up with a morning flagpole
by Scuba_steve August 26, 2018
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