Top Definition
Allowing your boner to stand straight up, making it visible to all who are around.
Girl 1: "I think he's into you"
Girl 2: "Why?"
Girl 1: "Because he was flagpoling during your entire conversation."
by Jerry C. August 16, 2011
Leaving the country solely for the purpose of re-entering so that you can activate a new immigration document.
ROB: I got approved for a new work permit for my specialized burger flipping job at McDonalds. I'm flagpoling tomorrow at the Niagara Falls border crossing.
JOE: What a joke. I'll show you where you can stick your flagpole.
by Werdly Smith November 02, 2011
having anal intercourse with a female looking like you are hanging her from your "flagpole"
Me: So how did it go with that girl you hooked up with man?
Peifer: Dude i was totally flagpoling her man
Me: well you might as well be gay right, i mean an asshole is an asshole right?
by Matt aka Stuffin McMuffin May 30, 2007

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