Noun; Part of the whole awkward "family" (i.e. Awkward Turtle). Used when someone says something awkward, and no one knows what to do. Used mostly when someone says something to try to be funny, and it doesnt work.
One makes the awkward flagpole by making fists with both hands and staking them on top of each other 3 times. On the 4th time, the hand on top opens, and the fingers start to wave and look like a flag.
One makes the awkward flagpole by making fists with both hands and staking them on top of each other 3 times. On the 4th time, the hand on top opens, and the fingers start to wave and look like a flag.
My english teacher said something awkward the other day, and our class didnt know what to do, so I made the awkward flagpole and we all cracked up...except my teacher who looked at me weird.
by hazelnut January 17, 2008
The time of night when it is so late that anything that anyone says or does appears to be absolutely hilarious. Technically is 3 am, but the actual time can vary.
Brett laughed so hard he couldn't breathe when he saw that mango thing. It must have been flagpole time.
by Laura-Bear June 1, 2007
after we got home from that mexican restaurant, we got back to my place and she wanted to try something new so we were about to start anal when she gave me a windy flagpole and i went home
by hornyllama69123 November 14, 2010
after we got home from that mexican restaurant, we got back to my place and she wanted to try something new so we were about to start anal when she gave me a windy flagpole and i went home
by hornyllama69123 November 14, 2010
a hanging wedgie on a flagpole.
i am a victim of wedgies to bullies. once i came to school early. unfortunately, so did the bullies. they saw me. they ran to me, took off all my clothes except my white undies, tied me up, carried me by my undies to the flagpole, made me drink five big glasses of water, and lifted me up by my undies to the top of the flagpole. one of the bullies videotaped the whole thing. the flag pole is REALLY high. every kid in school saw, and they laughed and took pictures and videos of me. i kept peeing. the buses left, and the teachers were at a meeting, so two hours after the buses left, one of the teachers saw and got me down. i was in that wedgie for 10 hours. my butt still hasnt recovered from that flagpole wedgie.
by Christopher Diddise March 11, 2008
i pulled out my favorite stroke book as i was greasing the flagpole.
Nate: i caught Jack greasing the flagpole. ha ha!!!
Phil: yeah, Jack likes greasing the flagpole, i caught him too! The jerk-off!!
Nate: i caught Jack greasing the flagpole. ha ha!!!
Phil: yeah, Jack likes greasing the flagpole, i caught him too! The jerk-off!!
by Mister jack Fister October 24, 2007
When your tighty whities are attached to the rope on the flagpole and then they raise it and that gives you a wedgie.
About two months ago, my parents went on a three week cruise. I got to school early, the bullies were waiting for me because they knew I wear tighty whities. They dreesed me down to my underwear and made me drink five huge glasses worth of water. It took so long for me to drink the water that by the time they had duct taped me to the rope, I was peeing on them. They lowered me, put ice in my underwear(it as winter) and started twisting my balls. OOOOOWWWWWW!!!!! This was a flagpole wedgie and they raised me up the full length and that is so high that the teachers never saw me. The only times they ever let me down was when the bullies fed me cafeteria food, EEEEWWWW!!!!, and made me drink water so I would pee and poop a lot. I wear extremely strong and stretchy so my tighty whities never ripped. Three weeks after I was raised up, my parents came home and called the police because I wasn't home. The police found me half naked attached to the flagpole covered in pee and poop! I was in that wedgie for three weeks and nineteen hours!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!! My older brother ripped the undies out of my asshole and that taught my nuts, penis and ass to not lett my brother near them.!!!!!!!!!!!! One kid had set up a video cam running the time that I was fed, watered, and raised. I couldn't change schools because that would be pointless. The asshole who taped put it on the web and the online yearbook. I was on CNN and News Channel 5.
by Briefboy September 21, 2008