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Something said to someone meaning that they should not be ashamed of anything or that they shouldn't be sad. It means that they should not stare at the ground in despair but rather pick their head up and stand tall.
Jim: John, why are you so sad?
John: I fucked Sally Parker and she's pregnant.
Jim: Sally Parker?! She's hot as fuck. Head up.

Jim: We just lost the state championship. I am so sad.
John: You guys are a great team and came a long way. Head up.
Head up by John Fuckerino December 9, 2013
When someone is "head up" they are angry or frustrated. It is mostly a Southern saying. You can hear it being said in The Rescuers film and other movies with Southern people.
When Gramps gets head up, his nose gets plumb outta joint
Head Up by DallasDeckard March 9, 2011
to evacuate, to leave somewhere with extreme quickness
'Yo man i heard Rico's coming, dude you better head up real quick'
Head Up by crookedcityinthetrees10 February 18, 2009
steer toward the wind.
"As the dark clouds rolled in and the wind picked up, the captain commanded, 'Helmsman, head up!'"
Head up by Arminkshipper April 18, 2025

Head up ass disease 

Head Up Ass Disease, in other words, someone has HUAD when his/her perception of a situation is so unusual or extremely inaccurate, most are left speechless.
She really thinks she's the best thing since sliced bread. She has head up ass disease.
Head up ass disease by ReallyGood January 2, 2012

Head Up In The Clouds

Said to someone who fails to comprehend his or her own present situation. Often perceived as a misinterpretation of past events or activities. It is advisable to remind the person in question (if you appear to be in verbally discernible range), of his or her mistake to avoid any forthcoming embarassments on his or her part.
(Brief exchange prior to an imminent Science Test)

Karl: Hey Ev! *shakes his hand* Fail with honor!
Evan: Thanks. You too.
Karl: Ayan! *shakes his hand* Fail with honor!
Ayan: What?! Hey, I'm passing!
Karl: Ughh.
Evan: Haha, head up in the clouds Ayan!