Grammar riddle that has little to do with Kanye West

Certain phrasings I come across from time to time make me stumble for half a second and re-read them. One of these is the consecutive repetition of a word, for example, “Before yesterday I had had doubts about bothering with this blog.” Even though it’s perfectly grammatical, it just seems so strange to lay those hads side by side.

But I discovered a riddle at with more consecutive repetitions of the word that than even Kanye West could manage in his song Stronger (“Now that that that that don’t kill me, could only make me stronger…”). And hot damn, girrl, this one was grammatically correct, too.

Now that that that that don't kill me. (From Wikimedia commons.)

See if you can solve this grammar riddle by inserting the correct punctuation:

I said that that that that that man wrote should’ve been underlined.

Don’t scroll down yet. I’m sure you’ll figure it out.

You’ll feel better if you solve it for yourself.

No, I said don’t scroll down!

OK, fine – here’s the solution.

I said that, “That ‘that’ that that man wrote should’ve been underlined.”

If that doesn’t make any sense to you, you can click here for a detailed explanation.

But I think I managed to top the riddle with an extra ‘that’:

I never said that ‘that’; that ‘that’ that that man wrote should’ve been underlined.

I’m always surprised by the infinite possibilities of the English language… Have a go at creating something just as strange – something to raise a grammar Nazi’s eyebrows. I’d love to see the results!

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12 Responses to Grammar riddle that has little to do with Kanye West

  1. I’m confused. Don’t get it. But I’m sure a gramar Nazi will be knocking on your door soon. 🙂

    • beaugamble says:

      Oops, I guess I didn’t actually explain how the sentence works. I edited the post to include a link to an explanation, if you’re interested.

      But thanks for stopping by again 🙂

  2. leadinglight says:

    That is rather cool ( no pun intended).

  3. Okay, I’m bleary-eyed now and ready to be proven incorrect, but here is my try at seven “that”s:

    I didn’t say that; that that ‘that’ (that ‘that’ that was underlined) was the only one.

    Sometimes I just can’t walk (or click) away from a challenge! Thanks for giving me that one.

  4. A couple of the “that”s were italicized when I worked this out on my computer, but I couldn’t get that formatting to show up here. I think that could have reduced your reads to five! This was a lot of fun — I’ll be back!

  5. Haha, fun. I stumbled to your blog from a very kind comment you left on a stranger’s door, one of the freshly pressed blogs. If I were feeling clever at the moment I would find a way to add in a string of that’s into this comment ~

    All the best ~

  6. Nicole says:

    Fascinating, I thought it was rapper editing rather than a legitimate sentence.

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