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  1. Nate Winchester
  2. Caption This
  3. Monday, 18 January 2021
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Hey everybody! Hope you're all doing well. For our previous contest, I was not disappointed with the dog jokes. Thank you for those. However 2 entrants both made a deep cut reference to S5's "Changing Channel" which made me laugh. Blsedbx3's wasn't bad, but I thought AlyCat22's version of the joke worked slightly better with Sam's facial expression. Congrats, AlyCat22.

This time, we go to #21 of our top 100 list. From episode 4.16 "On the Head of a Pin" a bit of Anna and Cas.
https://thewinchesterfamilybusiness.com/images/CaptionThis/2021/SPN_04x16.jpg

The first 50 winning entries are here. Winning entries numbered 51-100 are here. The winners of 101-150 are here. And 151-200 are now here. Winners #201-250 will be coming soon.
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AlyCat22
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Anna: "Just remember, I had him first!"
  1. more than a month ago
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  3. # 1
AlyCat22
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Cas: "He's partial to trench coats."

Anna: "And lady parts."
  1. more than a month ago
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  3. # 2
AlyCat22
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Anna: "He likes women Cas. Don't beat yourself up about it."
  1. more than a month ago
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  3. # 3
AlyCat22
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Cas: "Perhaps a different tie..."

Anna: "Forget the tie Cas. Boobs. You need boobs."
  1. more than a month ago
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  3. # 4
AlyCat22
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Cas: "Dean doesn't like to be watched while sleeping."

Anna: "I'll stop if you will."

Cas: "We'll just be very quiet..."
  1. more than a month ago
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  3. # 5
AlyCat22
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Cas: "Nice coat."

Anna: "Thanks! Trenchcoats-R-Us."
  1. more than a month ago
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  3. # 6
AlyCat22
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Anna: "Thats... disturbing."

Cas: "I take it you've never seen Dean eat pie before."
  1. more than a month ago
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  3. # 7
AlyCat22
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Cas: "Do you know how many feathers you left scattered all over the back seat?"
  1. more than a month ago
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  3. # 8
AlyCat22
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Anna: "What's this?"

Cas: "An alternate universe where Sam is a horse detective..."
;)
  1. more than a month ago
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  3. # 9
AlyCat22
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Anna: "What's this?"

Cas: "An alternate universe where Sam is a walking Texas Ranger."
  1. more than a month ago
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  3. # 10
AlyCat22
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Anna: "What's this?"

Cas: "An alternate universe where Dean plays an angry, angsty super hero."

Anna: "You just described our Dean."
  1. more than a month ago
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  3. # 11
AlyCat22
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Anna: "What's this?"

Cas: "Alternate universe where Sam is a Texas Ranger."

Anna: "Save a horse, ride that cowboy!"
  1. more than a month ago
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  3. # 12
AlyCat22
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Anna: "What was that?"

Cas: "My guess? The Guinea Pig Sam said we got that I've never seen."



*Poor Cas. He was so excited for a moment*

AC22
  1. more than a month ago
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  3. # 13
Marion
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Anna "should we wake him?"
Cass " look at my face Anna, this is what happened last time I disturbed Dean's dreams, do you think it's a good idea?"
  1. more than a month ago
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  3. # 14
Marion
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Anna " don't they look adorable when they're asleep?"
Cass " so long as you don't sneak a peek into their dreams"
Anna " Cass, Dean's told you a million times about personal space"
Cass " actually it's a million and thirteen, but whose counting?"
  1. more than a month ago
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  3. # 15
Marion
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Cass " That hole in the wall was already here when we arrived, right Anna?"
Anna " Absolutely. Already there. No Impala's were anywhere in the vacinity"
  1. more than a month ago
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  3. # 16
AlyCat22
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Cas: "So, how was it-"

Anna: "I told you Cas. We're not talking about my hook-up with Dean!"

Cas: "-when you hacked out your grace and fell."
  1. more than a month ago
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  3. # 17
AlyCat22
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Cas: "So how was it?"

Anna: "What? Do you mean the glorious, energetic, lengthy, awe inspiring ;) sex with Dean?"

Cas: "Bitch."
  1. more than a month ago
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  3. # 18
AlyCat22
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The Emoji from my last post was a mistake. It just snuck in there. Tho I'd be smiling too if I were Anna
  1. more than a month ago
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  3. # 19
AlyCat22
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Cas: "So how was it?"

Anna: "Our talk? I think Dean will-"

Cas: "No! The hard core sex in the backseat of the Impala!"
  1. more than a month ago
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  3. # 20
AlyCat22
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Cas: "Watching Dean is my job. Every moment."

Anna: "You're saying you saw us having sex?"

Cas: "Yes and he was magnificent!"

Anna: "He?"
  1. more than a month ago
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  3. # 21
AlyCat22
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Cas: "So how was it?"

Anna: "The sex? Deans so good he shouts out his own name."
  1. more than a month ago
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  3. # 22
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