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  1. Nate Winchester
  2. Caption This
  3. Sunday, 16 June 2019
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Awesome, job, everyone! I thought wild-card style phone conversation would get the creative juices flowing and you all did not disappoint. A dozen-and-a-half entries in the previous contest and it wasn't easy pickings. And while I don't normally like to encourage the shippers...

Jennifer's entry was pretty funny (congrats, Jennifer). AND it served as a great set up for this week's contest!

From episode 8.02 "What's up Tiger Mommy?" we have Benny meeting said angel. Dare you continue the "arc" of the CT season? Or do you invent a new gag? I eagerly await your efforts. :D
https://www.thewinchesterfamilybusiness.com/images/CaptionThis/SPN08x02.jpg

The first 50 winning entries are here. Winning entries numbered 51-100 are here. 101-150 coming soon.
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White_Bat
WFB Member
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1
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Undo
Benny: Your hiatus beard needs a little work there, son.

Cass: I'm not your son.
  1. more than a month ago
  2. Caption This
  3. # 1
AlyCat22
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1
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Cas: “Strange trench coat...”

Benny: “It’s a pea coat.”

Cas: “You URINATED on it?!?”
  1. more than a month ago
  2. Caption This
  3. # 2
cheryl42
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1
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Benny: So do you think I've got a shot?

Cas: Maybe...he seems to be open to other species...
  1. more than a month ago
  2. Caption This
  3. # 3
AlyCat22
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2
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Benny: *Winks*. “What happens in Purgatory stays in Purgatory...”
  1. more than a month ago
  2. Caption This
  3. # 4
AlyCat22
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Benny: “Bendean? Deannie? Admit it, you’re jealous!”
  1. more than a month ago
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  3. # 5
AlyCat22
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Benny: *Winks* “You can grab me tight and raise me from perdition anytime!”
  1. more than a month ago
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  3. # 6
Alyssa Zahn
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1
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You're the one Dean wouldn't shut up about?
  1. more than a month ago
  2. Caption This
  3. # 7
AlyCat22
WFB Member
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1
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Benny: "Heaven must be missing an angel!"

Cas: *Blushes*

Benny: "No, seriously. This is Purgatory, what the Hell you doing here?"

AC22
  1. more than a month ago
  2. Caption This
  3. # 8
AlyCat22
WFB Member
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1
Votes
Undo
Benny: "The angels returned!"

Dean: "Did he bring pie?"

Cas: What? Of course not!"

Dean: "You're dead to me Cas!"


AC22
  1. more than a month ago
  2. Caption This
  3. # 9
AlyCat22
WFB Member
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1
Votes
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Cas: "I raised him tight and-"

Benny: "Yes, but did he carry YOU inside his arm like a little blood baby?"

Cas: "No. And gross!"

Benny: "See? He likes me best!"

AC22
  1. more than a month ago
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  3. # 10
Laura
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1
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Don’t forget Cas, I was in Dean’s arm. I seen his vascular system.
  1. more than a month ago
  2. Caption This
  3. # 11
AlyCat22
WFB Member
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1
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Cas: “Dean knows. The cats out of the bag.”

Benny: “Meeeow!”


AC22
  1. more than a month ago
  2. Caption This
  3. # 12
AlyCat22
WFB Member
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1
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Cas: “So Deans going to ride you out in his arm?”

Benny: “Yeah. He’s my DUber!!!”


AC22
  1. more than a month ago
  2. Caption This
  3. # 13
AlyCat22
WFB Member
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1
Votes
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Benny: “C’mon. Try it on!”

Cas: “I refuse to wear a coat that has been urinated on!”


AC22
  1. more than a month ago
  2. Caption This
  3. # 14
Charlie Tague
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1
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“YOU’RE the angel? I thought you’d be taller!”
  1. more than a month ago
  2. Caption This
  3. # 15
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1
Votes
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Benny to Cas: Seriously you HAD to kiss him?
  1. more than a month ago
  2. Caption This
  3. # 16
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