Holiday Captions For Awful People

Ho x 3!


With Christmas fast approaching, America’s holiday traditions are in full force: overeating while forgetting that gluttony is a sin, giving gifts you can’t afford to relatives you can’t possibly like and, all the while, feeling like you’ve contributed to the peace on Earth and goodwill toward man because you spent $.99 on a can of cream of mushroom soup and dropped it into the donation bin at work.

And so, I felt that it would be nice to share a little Christmas spirit with my readers (both of you) and all of the Google-bots that truly are the beating heart to my blog’s self-esteem.

Feel free to download these images I do not own and share them with your loved ones. Or just share them with your family.

Christmas For Men



Bob’s Christmas Story



Why Bill No Longer Invites Co-workers To His Parties



Mr. Gundersen’s Thoughtful Gift

Mr. gundersen's gift


It’s Slinky!

It's Slinky


Santa’s Preferred Brand Of Cheer



The Well-Intentioned, But Ultimately Misguided, Gift Of The Magi



So, yeah, there’s a type-o in one of those, but it was too late to edit it, so you’re just going to have to deal with being let down by me this holiday season.


Yeah, yeah, I know! It’s all my fault that you drink! I don’t measure up, I’m not good enough, I’m not pretty enough! You’re constantly disappointed that I’m not like that Trudy’s son. “Trudy’s son has such a nice blog. It never has any errors on it. He’s very clever, too. Why can’t you be more like him?”

Oh my god, I hate you so much!

Happy Holidays, everybody!

55 thoughts on “Holiday Captions For Awful People”

    1. If Trudy’s son did blow it out his ass, I’m sure I’ll have to listen how that it had been blown out perfectly and “with class” and “oh, such grace with his buttocks muscles” and, Ugh!


  1. I did notice you forgot the “it” in the picture with Marcia but that’s only because I’m an asshole who should be married to Bill and/or related to the Flendersons. Merry vintage Christmas calahan!


  2. Pssht. Calahan, don’t let anyone tell you that you are not pretty enough! You are the prettiest man I know. Even prettier than Trudy’s son. In fact, I didn’t see the typo because I was distracted by all your prettyness.


  3. Works of art, every one. Regarding the Cadillac-owning 19-year old–well, isn’t that why we sock away money in IRAs and 401Ks?–So that in late middle age we can, however briefly and at no small cost to our personal lives, buy back some of that sex-appeal that we never really had in the first place?

    Also, I’ll grant you that it’s a foot-in-mouth situation for Bob, but the Flendersons really do suck.


    1. The worst part is that the Felndersons weren’t even invited. They assumed they were, but they weren’t. On top of that, the gifts they brought were all free samples from Mr. Flenderson’s job at the shoe polish factory.


  4. These are great!! I watched an old Christmas movie last night, and instead of cookies and milk, they left Santa a martini glass filled with wine, and a cigar. He lit that baby up and puffed some rings around the tree. It was beautiful.


        1. The fact that all of those orphans look exactly the same makes me think that somewhere is a couple that really needs to learn the concept of contraception. “We don’t know how this keeps happening!”


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