Writing Humour: Seven Challenges of Style

Smiley face changed

When it comes to writing, different people do different styles well. No style is easy be it reflective or expository or informative.

Writing to entertain can take various forms but the most challenging to pull off, according to me, is the humorous.


1. When the joke falls flat: You’re always taking a risk with jokes. Nothing fails so badly as a joke that fails to be funny. You end up worse off than you were before if you’ve insulted someone or if the piece had nothing else to recommend itself than the humour.

2. When the joke is taken seriously: When readers read quickly, they don’t catch the subtleties. In an older post, I happened to say that we are in a “post literary age.” The irony escaped quick readers who took it seriously and I ended up meaning exactly the opposite of what I intended. I’ve seen readers mistake articles in The Onion for real news but that’s probably a different story.

3. When the object of fun does not have a sense of humor: This point requires very little explanation. It’s hard to justify humour when everyone involved does not appreciate the fun. By the nature of the style, being funny often involves an object of fun unlike other kinds of writing.

4. When you can’t handle the sentence length: I’ve seen that if you believe brevity is the soul of wit but fail to pull off the joke, you come off as smart aleck-y. If you use long sentences overloading them with irony or word-play or too many qualifying clauses as part of the joke, you end up with clunky sentences that are not funny anymore. Fun requires the light touch and no handbook can teach you how to write funny sentences.

5. When shared subtleties of a culture escape the audience: Jokes that are immediately appreciated in one cultural setting or in a set of people who speak the same languages fall flat in a different setting or may even seem politically incorrect. If you’re trying this kind of humorous writing, you have to be super careful or stick within a certain community.

6. When shared values of a time are gone: When I watch old TV shows I find gay jokes or “taming of the shrew” style jokes about women that just don’t seem funny anymore. The fun has sort of evaporated with the times. But there may be equally hurtful jokes circulating in the present eliciting laughter which tell me we haven’t necessarily become better people but that those sensibilities have changed (fortunately in these examples).

7. When you don’t consider taste: There is “in your face” humor,Β  gentle and subtle humour and a million other styles that you can adopt. But unlike reflective or expository writing, the audiences for different kinds of jokes might be mutually exclusive so that the “market” is divided so to speak. You have to know very well who you’re appealing to and who you’re not. So one section will love you and the others hate you.

The humorous style is the most difficult to pull off because it has the least rules that lead to success and is the most difficult to control.

It also has a paradox embedded in it. When, as a writer, you run out of humour, you become tragic.

80 thoughts on “Writing Humour: Seven Challenges of Style”

  1. very interesting ideas. I particularly liked the idea that some people read through stuff quickly and that’s why they miss that it’s supposed to be funny. I’d never thought of that before and just thought they were too stupid to get it.


  2. This is such a relevant post for me because I write humorous stories. The genre I tend to favor is satire/comedy/fantasy. I actually consider myself to be very successful at using humor in the dialogue, sentences, and in the situations. I modeled a lot of Pratchett and Douglas. I found that subtle humor is usually best. It can be hard to ensure that your humor is universal enough to impress or amuse enough readers.


  3. Telling a joke is something far different from writing humor. i would love to say I write humor, but alas there is nothing humorous about the things I write. I want to thank you for liking “River Congo – Excerpt 20” on writingiam.wordpress.com, even though there is nothing humorous about the story or the situation. – Thanks again and Aloha -pjs.


  4. I love this topic. I once wrote a blog about writing humor (I guess I wanted people to think I was an expert?). But anyway I did some research and discovered that the main ingredient in humor is the unexpected. Irony. Element of something being opposite or backwards. Also, as someone else commented, we can’t force it or try too hard. Another thing is timing. Every line can’t be funny. Gotta intersperse jokes in the right places in between serious stuff. Which goes back to being unexpected.

    That being said, if someone doesn’t get our joke, why is that any different than if someone doesn’t get a deep and complex serious article? If it’s good then it’s good. Same with the cultural innuendos. All writing has the potential to fall flat on some cultures.

    So in a way I don’t agree with all seven of your points. But I do agree that writing humor can be hard.

    Nice topic!! :).


  5. Another stimulating post; I am regarded as having a fine sense of humour in real life (at least by those whose opinion matters) but have not tried to use it in my writing. This post and the comments could help me not leave one of my tools in the box.


  6. Punctuation can make for funnier lines. I don’t know how you manage without using semicolons. You could consider using a comma before the word but too!
    My joke about my friend often passes people by. He keeps drinking brake fluid. I told him he was getting addicted to the stuff; he just said, “I can stop any time.” πŸ™‚


  7. I once believed that comedy should be kept out of literature and on the stage. I thought that you could only find humor in books when those books were lame joke books or silly Internet posts. This is a shame because I absolutely love humor and I love making the people around me laugh. To this day, I still believe that stand-up comedy is one of the greatest forms of entertainment.

    But you can insert humor in to literature and I no longer think it is that difficult. The number one thing to remember is that not everyone reading it is going to find it funny. That is all there is to it. Just like not everyone is going to find the same stand-up comedian funny.

    In my opinion, the easiest way to fail at humor in writing is by trying too hard and by relying too heavily on sarcasm. Sarcasm can be very difficult to show in written dialogue, especially if you are using very little narration. I always find it a good idea to have another character react to sarcasm in such a way that it gets the point across.

    Even that is not guaranteed to work. Some people have a sense of humor so abstract that you might think that they do not have one at all and then you see them laugh at something that might have only garnered a chuckle from you.

    I would like to add an excerpt from a book by Philip Athans called The Guide to Writing Fantasy and Science Fiction. I believe this also applies to fiction and non-fiction of any genre.

    “If you’re not a funny person in real life–if you don’t routinely and spontaneously make the people around you laugh–don’t try it in your writing. Better your book remain serious and moody, devoid of humor, than sprinkled with clunkers.”

    Humor should come naturally. And who knows? Maybe if you don’t attempt to insert any humorous moments in to your story, your readers will find their own.

    I’m sorry this comment is so long. At this point I probably should have just made my own blog about it but alas, I’m already here. I had to leave this comment because I am currenlt trying my hand at a humorous short story that I hope to fill with irony, satire, and a few other jokes that are sure to insult some and make others laugh.

    Either way, I hope to at least get a reaction.


  8. I learned Humor Writing from Humor Writing Secrets, from Mel Helitzer & Mark Shatz. Some say it’s outdated, but I don’t think so.

    I think the toughest part of humor writing for stories is that you can’t use jokes, unless, perhaps, they’re in dialogue (and even then it’s tough). The reader is trying to get a full picture of the story, not just one-liners. So it makes sense to learn to write anecdotes,

    I’ve learned the best way is to surprise people; rewriting cliches have helped me do that. I’ve also found that it is easier to write humor in exposition than when action scenes are going on. When it is an action scene, dialogue is your friend for humor.

    I had this one scene (that I removed later on because it made less sense in the overall picture), where a priest and a knight were fighting a giant golem.

    “What’s that?” the knight asked.
    “What? I can’t see it. It’s your quest, not mine.”
    “Those words, floating in front of it.”
    “That’s the boss’s name. What does it say?”
    “I don’t know. I can’t read Japanese.”
    “You can’t read English!”

    Taken out of context, but if you knew the scenes before, where it’s subtly revealed the knight can’t read at all, it makes more sense.


  9. Wonderful post! Humor is tough. Many of my stories do have a humorous line or two, but I don’t go for the ‘rolling in the aisles’ type of funny – just feels forced if I try to write it that way. I don’t want to offend anyone unnecessarily, so I often poke fun at myself…or stupid people in general. Often times this is one in the same. And in case my sarcasm could be taken seriously, I add a little smiley to make it obvious πŸ™‚ In real life, I’ve found that I can say just about anything with a smile and get away with it πŸ™‚ (See?)


  10. Hey! Thanks for “liking” my new blog. Very exciting new world! Your blog is so fun – good to connect. I took a class called Humor Writing, and it was most disappointing. Everyone wanted to write for sitcoms or be a stand-up comedian. I just wanted to write funny, ie, Anne Lamott. Thanks for your thoughts, and for visiting my blog.


  11. I was just talking to my husband about this! People who know me understand my sense of humor, and I am not for sure if it comes off as humorous in my writing or not… but what scares me is that people who don’t know me, do not understand my sense of humor. LOL So I just go ahead, and say what is necessary and let it flow πŸ™‚


  12. I followed your “like” to your blog and it is wonderful! I am very inspired and look forward to reading your posts. I would love to get your perspective and advice as a beginning blogger.



  13. Nice post and very well said.
    I tend to be a bit flippant, quick flippant remarks that sometimes upset without me realising. And I think mood has something to do with it too. Sometimes I get humour and sometimes it’s wasted on me.


  14. There are so many “How to–” out there about writing humor and most of them say the same thing. You added a different level of meaning to the question with your comments about sentence length, shared values of time, and the in-your-face- know-your-audience humor. Humor mostly turns into humor when we laugh at someone’s expense. That makes humor quite tricky. Good job!


  15. I totally agree! Humor is damn hard to write. I tend towards the self-deprecating style, and I’m sure it irritates some people, but oh well. I operate by that one bit on Vonnegut’s crib sheet: “Write to please just one person. If you open a window and make love to the world, so to speak, your story will get pneumonia.”

    My one person? Me. I realize that sounds sort of sad, to write for my own entertainment, but hell, there are a lot of people out there who have a similar sense of humor and with any luck, they’ll find my work and laugh with me.


  16. I have a tendency to opt for the fuck-it attitude which is: if I chuckle to myself every time I read it, it’ll be good enough… surely. And then blame everybody who doesn’t get it for not having as wicked a sense of humour as I. πŸ˜‰


  17. Another thought-provoking post. Humour is so necessary and so difficult to define. I am writing to inform and hopefully to entertain, but I very rarely venture to use a “humour” tag. I suppose I am dead-pan in my blog, as in real life!


  18. I’m so glad I’m aware that my own written expressions of humor are mostly too dry and sometimes too silly, so that I rarely attempt to inflict them on readers.

    I really value finding writing that makes me laugh.


  19. Humor is the hardest thing for me to write, but when I do pull it off, it feels so good! Great post. πŸ™‚


  20. Switching styles can be difficult. If you become popular with a particular style and then try to write something different, readers can take it badly. I’ve seen this in action on a couple of blogs. Great Post.


  21. #4 is an especially good point. I know many folks trying to write parodies who start with an amusing notion and turn it into a belabored sentence. It’s a great exercise to listen to someone like David Sedaris read his humorous essays aloud and note how often his careful structure enhances the effect.


  22. Thank you for this. My blog is primarily humor. Or at least that is what I strive for. I guess my style would have to be “dorky” for lack of a better word. On the rare occasion that I write something serious, there is a joke hidden somewhere or a surprise people aren’t looking for. I can only think of a couple of my posts that weren’t either primarily humor or at least laced with it. I usually poke fun at myself, my dog, my dead parents, or things in pop culture that are up for grabs. It’s when I write something heart felt or serious that I am timid. I would rather let people decide whether or not they want to laugh at me than to bare my soul and write something serious. Heaven forbid the blogosphere finds out I have a brain in my head after all.


    1. That’s an excellent point: “than to bare my soul and write something serious.” Humour can be a good tool for showing disinterestedness when things are too painful. Sort of black comedy.


      1. Well, If you look at my blog, I do keep it light for the most part. But I am taking part in a photo challenge, and one of the entries just didn’t strike me as funny, so I wrote a very short love letter based on what the picture said to me. I was actually too embarrassed to let my husband read it. “Don’t bother” I told him. “It’s not funny.” I guess my humor is my armor. He read it anyway. He reads all of my stuff, even if it’s crap. πŸ˜‰


  23. This is great–clear and to the point. My journalism students often want to use humor and don’t generally do a good job with it. This fall, I think I’ll make this post required reading. Thanks! (I don’t try to write humor myself–it’s too hard.)


  24. In my own writing, outside of the blogosphere, I consider myself a humor essayist. I struggled, and still struggle with why people would want to ready and the fear that people would not think I was being funny at all. My mentor told me , that it is not about the pointed jokes but rather the humor-colored- lenses you see the world through. Whether it’s some lines of self-deprication or a dull detail of life you notice that others might not. That is what makes your writing connect to your audience, and keep them entertained.


  25. Interesting. Having published three ‘straight’ novels (in the contemporary/crime/mystery genres), my next work in progress is a tongue in cheek account of life on a remote British island. Kind of ‘Cold Comfort Farm’ on a rock in the Atlantic.
    It’s keeping me amused but I haven’t tried it on any readers yet. I know I can do drama – I’ve still to discover whether I can do humour too.


  26. I may not have caught the irony of your post-literary comment. I must say, however, that your post did cause me to reflect upon the nature of story as a vehicle for telling us live should be lived and the fact that there are so many vehicles out there in the blog-era telling us how to live, we bypass the novel for time… we’re wrapped up in reading blogs and other posts. It can become obsessive.


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