When you screw over your soldiers or employees because you can't get over your own bitterness. Applies to all people who revel in ruining the lives of others because of their own whimsical opinions. Common symptoms of "A Callahan" include Napoleon Complex, little dick syndrome, and others.
"Dude, my boss won't let me take vacation for my honeymoon. He's pulling a Callahan on me."
"I literally had COVID but my professor won't let me make up the exam. What a Callahan."
by psyfloperator November 19, 2020
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In Ultimate Frisbee, you catch a disc thrown by your opponent in your endzone and score a point. It is the coolest thing in Frisbee.
OH MY GOD, KIP JUST CAUGHT A CALLAHAN!
by hotdish March 28, 2009
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a friend of the dream team, and server operator on the dreamsmp he doesnt speak or show his face online, but is considered one of the funniest people on the dream smp just by using in game chat

his minecraft skin is captain america in a reindeer onesie
dsmp fan 1: did you see what Callahan just said

dsmp fan 2: yeah, he is so funny and he doesnt even talk!
by dreamsmpfacts January 26, 2021
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Person1: hey you know Callahan?

Person2:no?
Person1: he was on George's stream

I'm stupid
by Hi I'm a dream fan June 26, 2020
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Using ones left hand to flitter and twiddle the external genitalia, or snatch of a clueless female who is trying unsuccessfully to be humorous or witty.

At the recent Texas vs. Nebraska college football game, a female Nebraska fan (Who thought she was being quite funny.) was seen wearing a shirt with the slogan: Callahan This. The shirt also had a large arrow pointing down to the minge.
“She thought she was being hilarious, so I Callahaned her.”

“When my girlfriend tells a bad joke, I laugh sarcastically really loud and then Callahan her cooter.”
by George Henry October 28, 2007
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The T-shirt a pretty girl's wearing on an advertising picture of the same brand name, currently on the right of your screen (doesn't work all the time).
Jon : Hey dude, look on the right of your screen !
Doe : Oh an advertisement for Callahan !
Jon : You got it.
by SureIloveyoudarling August 17, 2009
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