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1.
Someone who, when seeing a group of "friends", thrusts his torso into the group and rehashes stories and memories of years ago because that is all he has in relation with the said group of friends. Every aspect of this person's life is awkward and cannot be anything but. When this person wants to begin a conversation, always being at the wrong time, he will turn his head back, tilt his neck, open his mouth slightly while squinting and vomit some random question that will never pertain to the conversation at hand. Also a know connoisseur of Hats 4 Cats™ and has a small kiosk in the crappiest mall in your neighborhood.
Group of Friends: "Hey do you guys wanna hang this weekend?" "Sure!" "Yea!"

Captain Awkward: "Hey, do you know when the flu season ends?"

Group of Friends: "Jesus Christ you are being Captain awkward right now dude..."
by JJTraficante May 09, 2011
 
2.
Boys who fail to remail chill after hookups but prefer to run out of the room and pretend you don't exist.
There I was drinking a keg in Capt. Awkward's room, when the boy came in and had to leave without any more beer because of his sketchy awkwardness.
by Bandito September 27, 2004