Caption This #443
Welcome to another week of Caption This! We did have fun with the Tracker captions for a couple of weeks. Kind of makes you wish Jensen was part of the permanent cast, doesn’t it? Ah well, we got a couple of great captions out of it.
So, who won Nate’s choice for Caption This! #442? Well, the choice was made because I am the non gamer in a family of gamers and I thought this caption was just perfect. Colter’s comment reflects my world. Congratulations paladinteacher!

So, now for this week’s contest. I got a little nostalgic and thought we should do something retro. What a better episode for retro quirky fun than season two’s “Tall Tales.”
Got any good ideas? Gotta love Dean’s chipmunk face!
I’m also offering a little extra credit. I found this one while going through the episode gallery. It’s one of my favorite shots of the series. It also isn’t fair to make this part of the contest in my mind. I always thought this freeze frame never needed any words, but hey, that just might be me. If you could caption this, what would it be?
The real contest is on the first caption, the second is just for fun. Make it real hard for Nate to pick a winner!
Instructions on How to Enter
Scroll all the way down to Disqus below:
Click on one of the icons to log in with an existing social media account (Discord, Facebook, X, Google, etc) or click the “Name” box that is next to all the icons. It will bring up the following screen:
There you can create a Disqus account, or you can check “I’d rather post as a guest” (that small check box after the 5 terms and conditions) and provide a screen name (that will be posted with your caption) and your email address (which will NOT be posted. It just keeps out all the spam responses). Enter your Caption in the “Join the Discussion” text box then hit the arrow to submit.
Here are the past winners:
Okay, time to Caption This!

Alice Jester is the founder, editor-in-chief, head writer, programmer, web designer, site administrator, marketer, and moderator for The Winchester Family Business. She is a 30 year IT applications and database expert with a penchant for creative and freelance writing in her spare (ha!!) time. That’s on top of being a wife, mother of two active kids, and four loving (aka needy) pets.



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