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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
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1
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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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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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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
  2. Caption This
  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
  2. Caption This
  3. # 6
Alyssa Zahn
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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
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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
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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
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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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Don’t forget Cas, I was in Dean’s arm. I seen his vascular system.
  1. 4 weeks ago
  2. Caption This
  3. # 11
AlyCat22
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Cas: “Dean knows. The cats out of the bag.”

Benny: “Meeeow!”


AC22
  1. 4 weeks ago
  2. Caption This
  3. # 12
AlyCat22
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Cas: “So Deans going to ride you out in his arm?”

Benny: “Yeah. He’s my DUber!!!”


AC22
  1. 4 weeks ago
  2. Caption This
  3. # 13
AlyCat22
WFB Member
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1
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Benny: “C’mon. Try it on!”

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


AC22
  1. 4 weeks ago
  2. Caption This
  3. # 14
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1
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“YOU’RE the angel? I thought you’d be taller!”
  1. 4 weeks ago
  2. Caption This
  3. # 15
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1
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Benny to Cas: Seriously you HAD to kiss him?
  1. 4 weeks ago
  2. Caption This
  3. # 16
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