Unfortunately He Asked.

Recently a friend told me he was looking for t-shirts that would make people “smile, or perhaps want to start up a conversation.” I like wearing unusual t-shirts, and in my experience people seem to be too shy to comment on them. Or sometimes I’ve been in a conversation for several minutes only to have the other person say, “Oh, hey, I just noticed what your shirt says.”

There are numerous places on the web where you can design your own t-shirt, and I started thinking about possibilities for my friend. Playing around on Customink here are a few I came up with:

tshirt1tshirt2 tshirt3

This one seemed misleading and more than slightly inappropriate, but would get the job done:


I call this one The Reverse Travis Bickle.


The one t-shirt of mine that does seem to get comments is my Lemony Snicket t-shirt that was given out as part of a promotion for volume 11 of A Series of Unfortunate Events, The Grim Grotto. The problem is most people don’t get it.


“What am I supposed to watch out for?” is the question I usually get. And they don’t get it if they see me walking away either.

snicket2 They’re very funny, fun books, but for some reason when I tell people it’s a book their eyes glaze over and I can tell they think they’ve started a conversation with the wrong person.


Facebook Comments


  1. Gina

    I like your designs Christopher. My favorite is the “illiterate” one. I don’t wear t-shirts but if I did I think I would have a blast designing inappropriate t-shirts online. The kind that I would make would be amusing to me but probably not appropriate to wear in public. Something like:

    “You’re in luck! (front) My herpes is in remission! (back)

    OK, I’ll refrain from writing any more here because every example I think of is NSFW.

    1. Christopher Waldrop (Post author)

      I think the people who create the design-your-own sites know people are going to come up with sick, disturbing things they, the creators, never even imagined. And if they don’t know that’s going to happen they’re completely unfamiliar with the internet.
      What I’m getting at is feel free to share any other examples because they’re probably quite tame in comparison to what other people have come up with.

  2. Spoken Like A True Nut

    I’ve always wanted a t-shirt that says “can’t touch this” in Braille.

    1. Christopher Waldrop (Post author)


  3. Ann Koplow

    Love the t-shirts, Christopher. I’ve created three t-shirts with CustomInk and I’m working on a fourth. They’re not a funny as yours but they do start conversations.

    1. Christopher Waldrop (Post author)

      Starting conversations is what matters. I’d like to see your t-shirts. I’m always in the market for new ones myself. I forgot to mention that my octopus t-shirts seem to start conversations too. Every time I go to an aquarium I find an octopus t-shirt in the gift shop, and I now have enough that I can wear a different octopus every day of the week.

  4. Leroy Strowig

    Where’d you get that Snicket shirt? I can’t find it anywhere.

    1. Christopher Waldrop (Post author)

      It was at a book publishing event. They gave them out with copies of The Grim Grotto. I’m sorry you can’t find it.

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