Sending emails is like a subtle mating ritual; if just one word is wrong, the whole thing will collapse into failure and embarrassment. It’s not so bad with friends, but when trying to communicate with co-workers, email will suck you down faster than a pit of quicksand. Luckily, almost everyone makes the same common mistakes, which can be avoided if you consult this handy list.

1. Sarcasm

This is a delicate tightrope act, because while you don’t want to seem boring, you also don’t want to risk giving the wrong impression, especially because sarcasm isn’t as obvious in typed communications as it is when you’re just talking. “That meeting today was totally rad; I learned sooo much” could easily be misinterpreted as “I actually enjoy going to meetings and un-ironically using words like ‘rad.’”

2. Overcompensating With Exclamation Points And Smiley Faces…

… that you can’t stop yourself from typing. Oh God, they’re going to think you’re such an idiot because of that last email. Do something! Do a winky face! And for the love of humanity, make sure you write “jk” so they know you’re just kidding! 🙂 🙂 🙂

3. Misreading Other Peoples’ Sarcasm

Oh wait… they didn’t think you were an idiot, they were actually agreeing with you. Now they’ll probably start inserting a bunch of winking smiley faces into their emails so you don’t misinterpret them.

4. Leaving Out Words

“You’re a demon!” gives people quite a different impression than “You’re a speed demon!”

5. Over-Explaining

Despite your best intentions to not seem pedantic, you’ve essentially just written a new textbook on whatever topic you were trying to explain.

6. Falling Down A Wikipedia Rabbit Hole And Telling People About It

Although you may have spent a fascinating afternoon reading about “Who Framed Roger Rabbit?,” the Cheyenne Mountain Complex, Alexander the Great’s horse and burial customs of Ancient Egypt, you should probably keep it to yourself until you find a way to work these interesting facts into casual conversation.

7. Hitting “Reply All”

Every human being lives in fear of accidentally hitting “Reply All” and looking like the world’s biggest idiot who has also inadvertently given out their personal information to the whole building.

8. Jokingly Threatening Someone

Even if the person you’re pretending to threaten is your best friend in the whole world, do not create an electronic document in which you state that you’re going to peel off their scalp and wear it as a hat.

9. Being Unsure Of When To Stop Replying

You said “thanks” in your last email, but they responded with more than just “no problem.” Does that mean you have to respond again? And if you write a lengthier sentence, will they respond? Who gets the last word? How do you break the chain of thanking and acknowledging and complimenting? You can’t just not respond, so your only hope is to drag this out until it’s time to go home.

10. Taking 20 Minutes To Craft An Eloquent Response and Ending Up With “Sure” Or “Thanks”

You want to seem witty and off the cuff, but after an agonizing of writing and re-writing awkwardly phrased replies, you delete everything and recognize that you’ve taken 20 minutes to come up with “Ok, thanks a lot!”

11. Inappropriate Misspellings

Intending to tell someone you’ll “shift things around” and then telling someone you’ll “shit things around” can either be hilarious or lead to months of embarrassment, depending on who the email was sent to. The same applies to writing “herpes” instead of “perhaps.” After a few of these almost suspiciously inappropriate misspellings, you’ll start to wonder if herpes you should start running Spellcheck on emails.

12. Emailing “Happy Birthday” After You Forgot To Say It In Person

Whoever’s birthday it is, they already know that you forgot it.

13. Sending A Panicky Group Email

Everyone needs to know that you weren’t the one who broke the water cooler! Really, you weren’t! You’ll sign an affidavit if you have to!

14. Being Physically Unable To Make Yourself Clear

“Are you sending the report back to me?”

“No, I need you to send it to me.”

“But you already have it.”

“No, you have it.”

“No, you have it.”

“I never had it!”

“Which report are we talking about here?”

15. Responding Too Vehemently

Sometimes we have things in the office fridge that we don’t want thrown away. Sometimes people threaten to clean out the fridge. Sometimes this leads to last-minute “DON’T THROW OUT MY SALAD I MADE IT LAST NIGHT AND IT’S ALL I HAVE LEFT IN THIS WORLD” emails.

16. Emailing The Wrong Person

Somehow, the people you complain about always have names that start with the same letter as the person you’re complaining to.

17. Dragging Out A Joke

You’re not quite sure how to keep this fresh, but you’ll try all day if it means not doing work.

18. Emailing The Person Two Feet Away From You

You could just walk into their cubicle/office/workspace and talk to them, but then you’d have to get up. You’re a busy person; email is totally acceptable in this situation. Except instead of emailing you back, they just pop their head in the door or talk over the cubicle wall, and you realize you could have done the same thing and now appear mildly agoraphobic for not doing so.

19. Too Much Or Too Little Photo Enthusiasm

When someone shares a cute photo of a child or pet, they can always tell when you didn’t actually look at it. They can also tell when you have no idea what to say, because you basically just started listing adjectives. “That is adorable, outrageous, sassy and purple!”

20. Frantically Emailing Someone Who’s Not There

Who does this person think they are? Do they think you don’t have anything better to do than sit around all day and wait for their response? Maybe you should email them again in case they didn’t see your first two, or maybe you should send them an irate manifesto about wasting people’s time. Or maybe they’re on vacation.