British Army slang for an Officer, but particularly an Officer that is upper-middle class or above, and has a total lack of skill or common-sense.
What!?! Leiutenent Grundy got his platoon lost again!?! Typical bloody Rupert...
by Savage Henry June 4, 2005
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Not neccesarily derrogatory.
by Diego November 14, 2003
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Rupert is basically your man, he has balance of his mates who he has a great time with and his love life, extremely musically talented, sad on the inside but covers it up with comedy and never opens up, he is sweet, funny, good looking, charming and cares for everyone, he tries to get along with everyone and is extremely tolerant, he has no racist, homophobic or bigoted views and is generally a wonderful guy
Guy:Where is everybody
Girl:they're all chillin with Rupert
by Triciawithavengeance April 15, 2012
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Rupert is a lovely, kind hearted person with an all round amazing personality. He smiles a lot and seems to be happy all of the time. When you are around Rupert you feel you are the person that matters and he will do anything to cheer you up when your down. Although if someone cries he feels a little lost... Rupert is not one to judge others unfairly, he see's every person as an individual. He is reasonably sensible and you can always reply on good ol' Rup to help you out.

He is absolutely adorable, very charming and i love to be around him. He is a really genuine, down-earth-guy and seems to have a heart of gold.
'I'd love to be with Rupert'
'Wouldn't everyone?!'
by PlebyCakes April 4, 2012
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When someone is acting like a dick. Acting like a know it all and never admitting when wrong.
Did you see that mess he made? Yes stiofan is a right Rupert
by Crazysteve July 28, 2016
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Critter Hunter.
Often finds Dean in the crawl with a lady Coon.
Holds regular critter hunts down in Seymour Indiana.
Has a secret diaper fettish.
When things are getting dull he covers himself in bacon grease and does the Jamaican nut slap to get a rise out of people.
Dresses like a lady and stares at himself in the mirror when no one’s home.
Likes to write music.

Enjoys a good mystery novel.
that Naked fella over there with a possum in a crate sure is a Rupert!
by Badger girl 317 January 15, 2022
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Either a bear or a sweet teenage boy
Ruperts are most commonly known for their creativity and lack of alpha male qualities. They are usually found at concerts or at youtube gatherings, they breed mainly in the summer and habitats include London and Devon. Ruperts normally migrate in small groups these groups can include a queer, a short person, a ginger, a tall boy and a quiet boy.
omigosh your such a rupert today!

what kind of a rupert are you??

what the rupert?
by Ishy Squish June 9, 2009
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