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  1. Nate Winchester
  2. Caption This
  3. Tuesday, 08 November 2016
  4.  Subscribe via email
Wow! The big 60! You guys realize we're now just 40 weeks away from ONE HUNDRED contests? Just seems like yesterday we put up our first 50 winners. If you want to be immortalized in the next 50, best start putting in your entries now!

Last week's contest ended with AlyCat22's victory.

You know what's in this week? Sweaters!

https://www.thewinchesterfamilybusiness.com/images/CaptionThis/SPN_0566.jpg

And if you have questions on logging in or voting, I have put instructions on how to participate in the Caption This! contest here.
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AlyCat22
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4
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Sam: "Hey Grandpa, did you see the fence opening or is your eyesight failing?"
  1. more than a month ago
  2. Caption This
  3. # 1
Mayhem
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3
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Dean: (panting) I barely made it over that fence. Sam, I feel old ....... and I know I'm starting to look and sound like Sylvester Stallone. But to have to put on this grandpa sweater, which, by the way, makes me look 50 pounds heavier is more than I can take. What am I doing to myself? I mean, I look like a fat Sylvester Stallone !!

Sam: (Sam laughs gleefully) Yes, a fat, sweaty, Sylvester Stallone sock-puppet. Here, let me roll up my sleeve, Dean, and......
  1. more than a month ago
  2. Caption This
  3. # 2
cheryl42
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3
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Sam: I would make an old fart joke but I think the sweater says it all.

Dean: Says Mr. Rogers

Dean: Bert

Sam: Ernie
  1. more than a month ago
  2. Caption This
  3. # 3
AlyCat22
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2
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Dean: "My sweaters caught..."

Sam: "Now you know how I felt when I lost my shoe..."
  1. more than a month ago
  2. Caption This
  3. # 4
AlyCat22
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Sam: "8.2 for sticking the landing!"
  1. more than a month ago
  2. Caption This
  3. # 5
steffync81
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Sam: Dean, I'm sure there are lots of people who have to use an apple box to get over the gate. I'm not one of them, but...

Dean: Shut your face.

Sam: Jerk.

Dean: Bitch.
  1. more than a month ago
  2. Caption This
  3. # 6
steffync81
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Dean: I don't care what you say. Cowboy boots were part of why Dr. Sexy was sexy and I want some.

Sam: Whatever.
  1. more than a month ago
  2. Caption This
  3. # 7
steffync81
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Dean: He's my angel, Sam. Not yours.

Sam: Maybe it's time to learn how to share.

Dean: Nope, not happening.
  1. more than a month ago
  2. Caption This
  3. # 8
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Dean: Well, that just happened.
Sam: Crossroads deal? Demon possession?
Dean: Yeah.
Sam: Definitely.
  1. more than a month ago
  2. Caption This
  3. # 9
AlyCat22
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1
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Dean: "Pfffftttt! Acrylic. Real men wear wool Sam."

Sam: "Says the man wearing a Grandpa Sweater!"
  1. more than a month ago
  2. Caption This
  3. # 10
AlyCat22
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Dean: "Think I pulled a hammy!"

Sam: "You CLIMBED a fence, you didn't polevault over it!"
  1. more than a month ago
  2. Caption This
  3. # 11
AlyCat22
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1
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Sam: "Didn't you see the-"

Dean: "Testing my physical stamina Sam. A hunter must exploit every opportunity that presents itself t-"

Sam: "That's just a scarf stuck in the bushes Dean. Not a pretty girl!"

Dean: "Oh..."

Sam: *Smirks* "Man your eyesight IS going...."
  1. more than a month ago
  2. Caption This
  3. # 12
AlyCat22
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Dean: "I voted for Trump!"

Sam: "I voted for Clinton!"

Dean: "Figures..."

Sam: "Figures..."
  1. more than a month ago
  2. Caption This
  3. # 13
AlyCat22
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1
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Sam: "I endured Hell, Lucifers torture, soulessness, angel possession... but I don't think I'll survive that sweater on you Dean!"
  1. more than a month ago
  2. Caption This
  3. # 14
AlyCat22
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Sam: "What do you call that pose Dean? "Constipated Grandpa?"
  1. more than a month ago
  2. Caption This
  3. # 15
AlyCat22
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1
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Sam: "Shhh...listen Dean!"

Dean: "Ghost? Witch?"

Sam: "Nah, it's a jar of prunes calling your name!"
  1. more than a month ago
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  3. # 16
AlyCat22
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Dean:. "Whew! I should've stretched before attempting that..."

Sam: "Attemp-It was five feet Dean. Hardly a Decathalon event!"

Dean: "It's higher than it looks..."

Sam: "Oh, I'm sorry. You're right. Quick call ESPN!!!"
  1. more than a month ago
  2. Caption This
  3. # 17
AlyCat22
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Sam: "Impressive. Lemme guess what's next... Opening a jar of prunes?"
  1. more than a month ago
  2. Caption This
  3. # 18
AlyCat22
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1
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Sam: "You're probably dehydrated after such an impressive feat of athleticism! Should we stop and get you a sixer of Ensure?"
  1. more than a month ago
  2. Caption This
  3. # 19
steffync81
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1
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Dean: You think if we just stand here, the guy with the camera won't notice us?

Sam: I don't know, but it's worth a shot.
  1. more than a month ago
  2. Caption This
  3. # 20
AlyCat22
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1
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Sam: "The way you barely made it over that fence reminded me of how weak Season Elevens myth arc was..."
  1. more than a month ago
  2. Caption This
  3. # 21
AlyCat22
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1
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Dean: *Breathing hard*. "I almost caught it Sammy!"

Sam: "Season Elevens myth arc? Give it up Dean - it doesn't exist. Its a beautiful fantasy - just like unicorns..."



BOOM!!! There ya go Natester - hopefully not too late!!!
  1. more than a month ago
  2. Caption This
  3. # 22
steffync81
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1
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Dean: I've already got a costume, Sammy. Not changing it.

Sam: Dean... come on. We can't both be the pink power ranger.
  1. more than a month ago
  2. Caption This
  3. # 23
nightsky
Site Administrator
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'C'mon SAMMY...I MAKE THIS LOOK GOOD'
  1. more than a month ago
  2. Caption This
  3. # 24
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Dean : I use to be good at this what the hell
Sam : gee Dean you've really let yourself go
  1. more than a month ago
  2. Caption This
  3. # 25
nightsky
Site Administrator
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Sam: 'Do you think Trump would want to grab my junk in this clothes?'
Dean: '...uhmmm.'
  1. more than a month ago
  2. Caption This
  3. # 26
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