Caption This! #378
Updated 3/18: We are running the contest for another week! So, keep going with your creative captions!
I REALLY need to stop making these so hard! I’m not sure what happened on Facebook this week, but we didn’t get a single entry. Ditto for Twitter (not X!). I do thank our regulars on the WFB for giving it a shot!
I didn’t think this one was so bad. I had a couple in mind when I chose it, but yes, one of the them I said when introducing the caption, “Is that a spear or are you happy to see me?”
I took an odd approach when selecting this week’s winner. I loved Alycat’s Sam comment, and it just so happened I had a great one for Dean, so I merged the two together into one really funny caption (or at least I think so given my odd sense of humor). Despite the collaborative effort, said admin is not eligible for the win, so congrats Alycat22!
Alright, I’m going to do my best to make this week’s easier since the last two weeks have been difficult. I’m working on the season 15 photo gallery this week, and there’s no better episode in season 15 for amusing screencaps than “Last Holiday.” So many to choose from. I couldn’t decide between these two, so I’m going to choose them both! Caption for one, or both (or neither?). That way, maybe one of these will resonate if the other doesn’t. A winner will be announced for each. If one doesn’t generate enough comments, I might just toss it out and run with the other one. I guess we’ll see what sort of response there is!
Caption #1
Caption #2
Up to the challenge? Time to double bonus Caption This!
Here are the past contest winning entries:
- 1-50
- 51-100
- 101-150
- 151-200
- 201-250
- 251-300
- 301-350 – Now available!
- 350+ – Coming Soon. No seriously, I promise. I’m just finishing up the S15 gallery first. This is next on the list!

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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