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Take the batteries out of all the remotes in the house.
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Organize his workshop, bedroom, or other special place.
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Bribe his faithful dog away from him with a steady diet of Ring Dings.
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Shrink his underwear in the dryer and when he complains, innocently suggest that he's gained a few pounds.
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Stare at his forehead and when he notices, casually ask if there is any history of male pattern baldness on his mother's side.
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"Accidentally" fill the gas tank of his new Porsche with diesel.
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Repeatedly misplace the cordless phone, preferably in a different room each time.
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Repeatedly lose his cellular phone in restaurants around town.
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Loan his precious cellular phone to a pregnant girlfriend who "needs it more than he does."
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Insist upon a lot of "meaningful conversations."
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If you live together, have your mother fly in for a month-long visit unannounced.
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Reverse his contact lenses in their case.
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Snip a small hole in his fishing waders, then follow him with a camera to capture his "sinking" on film.
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Superglue the pages of his Little Black Book together.
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Give the secret stash of dirty magazines that he thinks you don't know about to his younger brother, who he hates.