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  1. Nate Winchester
  2. Caption This
  3. Monday, 24 June 2019
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I wondered if a bit of Benny & Cas would get some shipping captions made but you all showed commendable restraint in that regard. There were many good entries in the previous contest with AlyCat22 winning the day with an educational, yet childish entry. We all feel a little richer now in our knowledge of men's fashion, thank you AlyCat22.

Hmm... we're almost to the point of having done every episode Benny was in. No choice but to continue on to episode 8x05, "Blood Brother" and this time we let Benny interact with someone other than our boys.
https://thewinchesterfamilybusiness.com/images/CaptionThis/SPN_08x05.jpg

The first 50 winning entries are here. Winning entries numbered 51-100 are here. 101-150 coming soon.
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AlyCat22
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What can I say Nate. You inspire me! ;)


AC22
  1. more than a month ago
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  3. # 1
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Andrea: Sit down in that chair right there and let me show you how it's done.
Benny: I'm not the devil and this ain't Georgia, sweet heart."
  1. more than a month ago
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  3. # 2
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Andrea: sit down in that chair right there and let me show you how it's done.
Benny: Darlin, I ain't the devil and this sure as hell ain't Georgia.
  1. more than a month ago
  2. Caption This
  3. # 3
AlyCat22
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Andrea: “Take me upstairs and make passionate love to me!”

Benny: “Sorry. You’re not my type!”


*Ba-dum-hiss*. AC22
  1. more than a month ago
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  3. # 4
AlyCat22
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Andrea: “Take me upstairs and make wild love to me!”

Benny: “I...can’t!”

Andrea: *Gasps*. “Not - ED!?!”

Benny: “Nah. Handcuffs!”
  1. more than a month ago
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  3. # 5
AlyCat22
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Andrea: “And this? This is my lion tamer look...”


AC22
  1. more than a month ago
  2. Caption This
  3. # 6
AlyCat22
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Andrea: “Damn. I left my pith hat upstairs!”


AC22
  1. more than a month ago
  2. Caption This
  3. # 7
Laura
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I do like a little bondage in the morning Benny.
  1. more than a month ago
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  3. # 8
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Sammy Hagar’s “Love Or Money” is playing

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She says, "Money honey, that's what I want."
Just a whole lot of money
?
  1. more than a month ago
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  3. # 9
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“50 shades of Grey ... No, ... I learned this from 69 shades of Plaids”
  1. more than a month ago
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  3. # 10
AlyCat22
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Andrea: “And now I will play the harpsichord!”
  1. more than a month ago
  2. Caption This
  3. # 11
AlyCat22
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Benny: “It’s a pea coat.”

Andrea: “You URINATED on it?!?”

Cas: “See? It’s not just me!”

Andrea: “I’m a Greek Heiress. What’s your excuse?
  1. more than a month ago
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  3. # 12
AlyCat22
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Benny: “It’s a pea coat.”

Andrea: “You URINATED on it?!?”

Cas: “See? It’s not just me!”

Andrea: “I’m a Greek Heiress. What’s your excuse?”
  1. more than a month ago
  2. Caption This
  3. # 13
AlyCat22
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Benny: “It’s a pea coat.”

Andrea and Cas: “You URINATED on it!?!”
  1. more than a month ago
  2. Caption This
  3. # 14
AlyCat22
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Andrea: “You’re cologne... is it Oud?”

Dean: “No, Gods... arm pit!”
  1. more than a month ago
  2. Caption This
  3. # 15
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