Riddle Rough Drafts.

What walks on four legs in the morning, two legs in the afternoon, three legs in the evening, and when would be the ideal time for it to get health insurance?

A box without hinges, key, or a lid, but you followed the directions when you were putting it together. Did you save the receipt?

A train traveling at forty-five miles an hour leaves Vancouver heading east at 4:45am. A train traveling at thirty miles an hour leaves Poughkeepsie traveling northwest at 1:05pm. Explain to me again why this is so much better than flying.

You have two and a half bottles of conditioner and three quarters of a bottle of shampoo you swiped from a hotel. How many times do you have to travel before you have an even number of both?

On Monday there are five coffee cups in the office break room sink. On Tuesday there are four coffee cups in the office break room sink. On Wednesday there are eight coffee cups in the break room sink. Is anyone going to ask Kevin to just rinse one cup if he’s drinking that much coffee?

As I was going to St. Ives, I met a man with seven wives. Each wife had seven sacks, each sack had seven cats, each cat had seven kits, and what are the odds I turned around and went back when I saw what kind of people lived there?

You have three glasses of milk and three bowls of pudding. You drink one of the glasses of milk and, oh, wait, are you lactose intolerant?

What has no beginning, end, or middle and is circular and, oh, I just gave away the answer there, didn’t I?

A father and son are in a terrible accident. The father is killed and the son is rushed to a doctor. The doctor says, “I can’t operate on him, I’m a psychiatrist!”

Which came first, the chicken or the egg, and is putting mayonnaise on a chicken sandwich a double insult?

You’re faced with two guardians. One always tells the truth, the other always lies. Which one do you ask a question since they’re both major assholes?

There are four days that start with the letter ‘T’: Tuesday, Thursday, and I’ll tell you the other two tomorrow and yesterday.

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  1. Bookstooge

    I just had the song “Major Tom” start running through my head, but with the change “Major Asshole”. Thanks for that…

    1. Christopher Waldrop (Post author)

      Well, ashes to ashes, funk to funky, we all know Major Tom’s a junkie. Although I think it’s the guys on the ground who want to know whose shirts he wears who are the real major assholes.

  2. Authoress51

    I always add mayo to chicken sandwiches.

    1. Christopher Waldrop (Post author)

      Mayo and chicken sandwiches do go together nicely–otherwise the chicken can be too dry.

  3. Ann Koplow

    What lives in Tennessee, is owned by Dalmatians, is happily married, writes great riddles, is left-handed, and creates terrific blog posts? Oh, I gave away the answer there, didn’t I?
    Ann Koplow recently posted…Day 2364: Where would you go in a time machine?My Profile

    1. Christopher Waldrop (Post author)

      If the riddle is, who lives in Boston, is a talented singer-songwriter and ukelele player, and an all around great person who writes the best comments…well, I leave it to you to figure out the answer to that riddle.

  4. Arionis

    Thanks for the chuckle today! This reminded me of not exactly a riddle, but one of my wife’s favorite poems. I’ve slightly modified it for your sake…

    Ladies and gentleman skinny and stout
    I’ll tell you a tale I know nothing about
    The admission is free so pay at the door
    Now pull out a chair and sit on the floor

    On one bright day in the middle of the night
    Two dead boys got up to fight
    Back to back they faced each other
    Drew their swords and shot each other

    The blind man came to see fair play
    The mute man came to shout hooray
    The deaf Kevin heard the noise
    And came to stop those two dead boys

    He lived on the corner in the middle of the block
    In a two story house on a vacant lot
    A man with no legs came walking by
    And kicked Kevin in his thigh

    He crashed through a wall without making a sound
    Into a dry creek bed and suddenly drowned
    A long black hearse came to cart him away
    But Kevin ran for his life and is still gone today

    I watched from the corner of the table
    The only eyewitness to facts of my fable
    If you doubt my lies are true
    Just ask the blind man, he saw it too
    Arionis recently posted…One In A Million Shot(s)My Profile

    1. Christopher Waldrop (Post author)

      Wow. I’d completely forgotten that but I remember hearing that as a kid–well, a slightly different version that ended with “And came to stop those two dead boys” and then jumped right to the “If you doubt my lies are true…” So that’s almost three complete stanzas I’ve never heard before, not even when some kids on a Scout camping trip did it as a fireside sketch.

  5. Allison

    I gave my love a chiiiiicken, that had no bone…

    Fun riddles!
    Allison recently posted…Take Two, They’re SmallMy Profile

    1. Christopher Waldrop (Post author)

  6. mydangblog

    I laughed out loud at so many of these! I know how a lot of them are supposed to end, and your endings are SO much better!

    1. Christopher Waldrop (Post author)

      A lot of this came out of my frustration with the real riddles themselves. Especially the one about the young man being rushed to the doctor. I never had any trouble accepting that a woman could be a doctor so it was never a “riddle” for me.


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