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  1. Nate Winchester
  2. Caption This
  3. Monday, 25 January 2021
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Well I was wondering if the Cas/Anna double act would lead to a few shipping double entendres and thankfully you all did not disappoint in the previous contest. A few entries I considered but was warned that we didn't want the shippers to burn down the place so congrats to AlyCat22 for an entry which... you can interpret in whichever ship you prefer. :D

For this week, we had done all the others in our top 100 so now we're down to #25, episode 4.21 "When the Levee Breaks" which is another episode with Anna & Cas (I did not plan this)! But since we didn't seem to get much participation, I thought maybe we'd go with a bit of Mr. and Mrs. Walker. Should allow for plenty of meta jokes. ;)

https://thewinchesterfamilybusiness.com/images/CaptionThis/2021/SPN_04x21.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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Brittney Cole
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Sam did you really kill that demon with your fart.
  1. more than a month ago
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AlyCat22
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Sam: "I'll overlook soulessness and demon blood but I draw the line at being the shorter one in this relationship!"
  1. more than a month ago
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AlyCat22
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Ruby: "Its boy, boy, girl. Not girl, girl, boy, Sam!"
  1. more than a month ago
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AlyCat22
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Ruby: "Its not my fault you plummeted to the ground!"

Sam: "You said I didnt need the feather to fly!"

Ruby: "I thought you were the smarter brother."
  1. more than a month ago
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  3. # 4
AlyCat22
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Ruby: "DemonDean on speed dial? Whatever gave you that idea?"

Cas: "Ahem."

Ruby: "Bitch."
  1. more than a month ago
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  3. # 5
Marion
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Ruby " Don't look at me like that Sam, I wasn't the one that made your laptop freeze, again"
  1. 4 weeks ago
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  3. # 6
Marion
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Ruby " Ok, so I lied about the vegan bacon, sue me"
  1. 4 weeks ago
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  3. # 7
Marion
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Ruby " Quit whining, you only win Rock, Paper , Scissors because Dean lets you win"
  1. 4 weeks ago
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  3. # 8
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