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TOS Caption Contest #42: Awkward Moments

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And look what they did to Mr. Bigglespock!
 
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After 300 years, Spock was still waiting for a definitive end to the Sopranos.
 
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KIRK: "Uncle! Say Uncle! SAY IT!!!"
CHARLIE: "Why do they always go for the nipple?"
KIRK: "Okay punk, you asked for it...TITTY TWISTER!!!"
CHARLIE: "There's no 'right way' to pinch a nipple."
 
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McCoy, off-screen: "Ahem. When I asked you to go over the birds and the bees with him, this wasn't exactly what I had in mind . . ."


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Chapel entered Spock's quarters without knocking and discovered his preference for Andorian women.
 
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"'Are Vulcans succeptible to excessively dry skin and scalp'?

Why do you ask, Doctor?"
 
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After recieving his limited edition Charlie X sleeping bag, Kirk discovered he had ordered the X-small rather than the X-large. It was too late, though, as he had already managed to get both legs in.

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How many Kirks can you fit in a freak kid?
 
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Spock (off-camera): "Uncle Dwayne?"

McCoy (off-camera): "Dwayne?"

Kirk: "I know how this looks..."
 
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The human starship commander deposits his seed in the rectal canal of the younger human male of indeterminate career and purpose, allowing the species to continue...
 
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Charlie: (thinking) Why did I agree to wrestle with him? Damn! I looked! Okay, Charlie, think of something boring. Paneling. Yes, paneling is very boring. There's many kinds of paneling....and those damn tights he's wearing are so damn...tight. Oh, no, I looked again! Think, Charlie, close your eyes and think of something other than those tights and that bulge. Oh, damn! Paneling! Paneling!
 
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