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14 Hilarious Grammar and Spelling Mistakes


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Spelling errors, grammar mistakes, punctuation misuse, and an overreliance on technology have all resulted in some pretty serious proofreading disasters. Smarty pants like us see these “fails” and shake our heads wondering, “How did no one notice that?”

Whenever we see grammar mistakes, misplaced punctuation, and spelling snafus online or in our local grocery store, we cringe. But then we remember that’s why we’re here. The world needs proofreaders like us to save them from these eyesores. #jobsecurityforlife

That being said, we do enjoy a good laugh! Here are some of the most hilarious grammar, spelling, and punctuation mistakes we’ve ever seen. Sit back, relax, and get ready to laugh!

(BTW, have you ever struggled to spell hilarious? It trips me up sometimes!)

Quotation Marks Gone Wrong

9 hilarious grammar mistakes that’ll make you chuckle (or want to tear your hair out!)

So… aliens?

These are classic examples of quotation mark misuse! The unnecessary quotation marks on the sign, we have come to expect. Your guess is as good as mine as to why this punctuation issue almost always happens on signs.

hilarious grammar mistake

Love the sentiment, but it’s ok to just call them kids.

This is another example of quotation marks making us question the situation. Are they not really kids? Are they like gremlins that change if you get them wet or feed them after midnight?

X hilarious grammar mistakes that’ll make you chuckle (or want to tear your hair out!)

The unnecessary quotation marks on the magazine cover? Shame on them! Apparently, they had their reasons for using quotation marks, but they probably should have given it a bit more thought.

X hilarious grammar mistakes that’ll make you chuckle (or want to tear your hair out!)

We really hope this isn’t from the English teacher!

We don’t want to bash teachers here because they work very hard. But somebody, whether it’s their parents or their teachers, needs to show kids the right ways to use an apostrophe. This cute book will help young kids learn about punctuation through fun rhyming poems.

This type of apostrophe misuse bothers us so much that we made it rule #1 in our how not to use an apostrophe blog post!

punctuation mistake

A few commas could have saved so many people from holding their bladders all the way home…

If you want to avoid comma pet peeves, we’ve created the perfect blog post for you!

Homophones Can Be So Tricky!

X hilarious grammar mistakes that’ll make you chuckle (or want to tear your hair out!)

Homophones are tricky! They’re pronounced alike but have different meanings and spelling.

Mixing up they’re, their, and there is one of the most common homophone mistakes. If you find yourself needing to explain it to someone, here’s the difference:

  • There = that place
  • Their = belongs to them
  • They’re = contraction of “they are”
grammar mistake

Sometimes we also don’t recognize our learning, but this is just plain sad.

Got kids? Buy them this book! It’s an EXCELLENT choice for kids and adults alike. You’re guaranteed to learn something you didn’t already know about soundalike words!

No Spelling Bee Winners Here…

X hilarious grammar mistakes that’ll make you chuckle (or want to tear your hair out!)

What meanie told this person not to have a great day?! Ignore the hater and have an AWESOME day!

We have to admit “definitely” is a tricky word to spell. It’s one of those words you just have to sound out in your head as you spell it.

Ummm... You may want to rethink that, Mr. Chicken.

Ummm… You may want to rethink that, Mr. Chicken.

We think he would have had second thoughts if he’d known what was coming next!

X hilarious grammar mistakes that’ll make you chuckle (or want to tear your hair out!)

There’s a threat to the Christmas spirit! And it’s not cheap!

grammar mistake

Did she consent to that?

Thankfully, there are so many kinds of writing software online to help you avoid spelling issues like these! Check out the Pro Writing Aid and never mistake “wife” and “wifi” again!

You Should Have Had Someone Proofread That…

X hilarious grammar mistakes that’ll make you chuckle (or want to tear your hair out!)

This one cracks us up! We can forgive the typo in the word “birthday,” but what were they thinking when they iced the words “Mark with The Sea”!

grammar mistakes

While we agree that everyone deserves a little recognition, we think that Veteran’s Day is a bit more specific.

Yikes! Here’s a bonus one we couldn’t leave out.

Ok, maybe this one wasn’t too funny for the recipient who endured the pain to get this back tattoo, but we do hope they have a sense of humor. Hopefully, if you’re seeking a tattoo, you’ll find a 5-star tattoo shop you can trust with your permanent ink.

Our Take

Word nerds unite! We love sharing my word nerdiness with you guys! Not many people out there get as hot and bothered as we do about grammar, so it’s fun to have a safe place to share our grammar woes. We could use a few more of us in the world, right?!

Your Turn

Do you have a grammar or punctuation pet peeve? Share it with us in the comments!

If you’re looking for a great way to check your documents and social media posts before sending them, check out Grammarly!

If you want to learn even more about apostrophes, quotation marks, and other grammar-related fun, be sure to check out our FREE workshop. You can use those grammar skills to start your own freelance proofreading business!


  1. Someone told me on the ARMY’s AMINO app:
    Person: what’s you’re problem
    Me: apparently I am LOL ?
    Person: what
    Me: “you are” I’m not my own problem ?

    1. That comeback was both clever and hilarious—sometimes a little grammar correction makes the conversation even more memorable!

  2. This one isn’t a misspelling, but it’s noteworthy, and I was there when it happened.

    Had a client, a mid-level manufacturer here in Japan, whose president had spent two or three years in the UK, so he was convinced he was fluent in English. It was time for a new ad campaign, and he wanted to convey that his company led the industry.

    He suggested a visual of geese in a v-formation along with the phrase, “We break the wind.”

  3. “Mark with the Sea” – my guess is that the person ordered the cake over the phone and said: “Mark with a ‘C'”, meaning the guy’s name should’ve been spelled ‘Marc’. However, phonetically, it sounds like what was written instead.

  4. My favorite was seeing a sign on a restaurant that said, “Drive Through Window”. It means something entirely different without the hyphen.

    1. That’s so true, Harry! Thanks for sharing!

  5. I'm very happy with what you've said. I wanted to tell you how much I liked this post

  6. One of my favorites is a classified ad for a child's bunk bed claiming there is "room for one and a fiend."

  7. I am inspired by your course offering and information.

  8. Your writing is impactful and informative. Thank you for another great blog post.

  9. I appreciate reading your essay. Please post soon; I want to read it. I hope the next update goes smoothly. Very interesting and useful article.

  10. "I was watching a movie on a film app, and I couldn't stop laughing at the subtitles! At one point, a character dramatically said, ‘I no the truth,’ instead of ‘I know the truth.’ Another scene had ‘Your going to regret this’ instead of ‘You’re going to regret this.’ I don’t know who’s in charge of these translations, but it looks like grammar and spelling went on vacation! Honestly, these hilarious mistakes make the experience even more entertaining!"

  11. My favorite that I found on Facebook one time…

    I'm giving up eating chocolate for a month. Sorry, bad punctuation. I'm giving up. Eating chocolate for a month.

  12. I have a pet peeve (that) comes to mind…the word "THAT". I feel (that) it is overused. I am always rethinking my sentences to make sure (that) isn't needed, i.e. I know (that) she is a good student. You can tell (that) by her grades.

  13. I've been working on it in private, and I'm becoming better at it! Enjoy yourself, get more done, and impress others!

  14. Great roundup of hilarious errors! I especially enjoyed the section on quotation mark misuse—those signs really do make you do a double take. For anyone interested in sharpening their skills, the free workshop mentioned is a fantastic way to deepen your proofreading knowledge.

  15. Great roundup of common proofreading blunders! I especially appreciated the section on apostrophe misuse—it's surprising how often that causes confusion even among experienced writers. For anyone interested, the free workshop mentioned really deepened my understanding of tricky punctuation and helped me improve my freelance proofreading skills.

  16. Really enjoyed the humor in this post! It’s so true that misplaced punctuation can completely change a message’s meaning—your examples perfectly highlight this. For anyone interested in sharpening their skills, the free workshop you mention is a fantastic way to deepen understanding of common grammar pitfalls.

  17. This article made me smile! I especially appreciated the examples of quotation mark misuse—they perfectly show how punctuation can completely change meaning. For anyone wanting to sharpen their skills, joining the free workshop mentioned here is a fantastic next step.

  18. thanks for the day to all of this in the evening of the day to all of this in the best content ever for you and everyone else and useful content

  19. My favorite typo was on an engineering report I was proofing. Apparently, Jerry's fire-fighting expansion foam gets into all the nooks and grannies! (should have been nooks and crannies!)

  20. This had me laughing — grammar mistakes really are the best (and worst) kind of entertainment! It’s crazy how something as small as a misplaced apostrophe or quotation mark can totally change the meaning — or just make you do a double take. Thanks for the helpful reminders and the laughs! Definitely sharing this with my fellow word nerds. 🙌📚

    1. So true! Grammar slip-ups can be hilarious and educational all at once. Glad you enjoyed the post. Thanks for sharing it with your fellow word lovers!

      1. Totally agree! It’s amazing (and hilarious) how one tiny punctuation mark can cause so much confusion—or comedy! Grammar slip-ups keep things interesting, that’s for sure. Glad you enjoyed the post—and yes, fellow word nerds will definitely appreciate the laughs too!

  21. My pet peeve is the word amount. The word is used for everything now. "A large amount of people attended." What, is that 97 metric tons? Or is it, "A large number of people attended."

  22. As a writer, I'm always paranoid about letting a typo slip through. This list was a great (and funny) reminder that it happens to the best of us. The "public" vs. "pubic" example is a classic cautionary tale!

    1. Thank you for your comment! It’s true! Typos can happen to anyone, and that example is always a good reminder to double-check our work. 🙂

  23. I just happened to come across your article when looking for information online. The stuff on this website has really impressed me.

  24. This collection of grammar mistakes is absolutely hilarious! The "you're" vs "your" confusion and the "Mark with the Sea" cake mishap had me laughing out loud. Your examples perfectly capture how easy it is to overlook these errors.

  25. Great collection! As someone who works in editing, I've definitely seen my share of misplaced apostrophes and homophone errors. The "your/you're" mix-up never fails to make me chuckle, though I still catch myself making occasional typos too. Do you find that certain types of mistakes are more common in professional writing versus casual social media posts?

    1. Thanks for your comment! Yes, some mistakes do tend to be more common depending on the context. Professional writing often involves issues with punctuation, consistency, and style guide adherence, while casual social media posts are more likely to include typos, informal language, and homophone mix-ups. Careful proofreading is valuable in both settings. 🙂

  26. As a freelance writer, I've definitely caught myself making a few of these mistakes in first drafts—especially the "your/you're" mix-up when I'm typing too fast. It's reassuring to know even seasoned proofreaders slip up sometimes. Do you find that certain types of errors are more common depending on the industry you're proofreading for?

    1. Thank you for your thoughtful comment! You’re absolutely right, everyone makes mistakes, especially in first drafts. Different industries do tend to have their own common writing patterns, which is why understanding the context is such an important part of proofreading. We’re glad you enjoyed the article! 🙂

  27. This was such an enjoyable read! Some of these grammar mistakes were genuinely funny, but they also show how a small typo can completely change the meaning of a sentence. I especially liked the real-life examples because they make grammar lessons much more memorable. Thanks for putting together such an entertaining and educational article—looking forward to reading more posts like this!

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