4 Reasons I Feel Terribly Awkward When Sending Emails

4 Reasons I Feel Terribly Awkward When Sending Emails gmailAdmittedly, I’m a socially awkward individual.  I’m the guy who will occasionally not go through drive-thru restaurants due to fear of confrontation. I’m also the guy who won’t buy toilet paper in high-traffic supermarket checkout lines because he thinks he will be judged by other shoppers. Yes, I’m a little messed up in the head, but it’s not that bad… Really.

Unfortunately, this social anxiety often seeps into my virtual life, and it causes me issues with sending email. I know that these four are simply common issues (actually, I’m just hoping that they are), but I thought this would be a great time to just get them off my chest.

The Tone Sometimes Seems Off

This is an issue that plagues all of us, for there’s never really knowing how one’s tone is in an email. Sometimes the friendliest guy in the world can send an email that sounds overly commanding and harsh. I know that I’ve been guilty of it. Other times, I sound like a whiny schoolgirl who is spouting off everything that is going wrong in their life.

4 Reasons I Feel Terribly Awkward When Sending Emails confused

For instance, my computer broke this week. I emailed Mark about it to explain why I needed a few more hours to get my article turned in, but after re-reading the email… Phew. I seemed as if I was about to sit down in the middle of the floor and cry. (I believe it may be because I’m a little too detailed with my emails…)

My Jokes Aren’t That Funny

Many of you may have been in this similar situation, so I’ll ask. Have you ever ended an email with what was supposed to be a corny, light-hearted joke? Or perhaps one that is witty and playful, but if taken seriously, could appear rather condescending to the receiver?

4 Reasons I Feel Terribly Awkward When Sending Emails laugh

My friends, time and time again I have tried to add a joke to an email only to discover that humor does not travel well over the Internet. There has even been the instance in which I have received a reply, “Haha, Josh. I don’t know if that was supposed to be funny or not. I’m really not getting it! Hope you are doing well, though.”

It was if my ego had been punched in the face.

I Send Emails When I’m Really Tired

One of the bad parts about working from home is that I sometimes put off email responses until late at night. Why? Well, I’m afraid my response will sound stupid. (I do the same with missed phone calls, but that’s for another article.) Anyway, what happens is that I don’t fully know exactly what I’ll say.

4 Reasons I Feel Terribly Awkward When Sending Emails sleepy

However, the issue is that at this point, I’m never really in control of what I’m going to type. There are many occasions in which I write my response, fall asleep, and then wake up to a message that I can’t believe I wrote. It’s as if I become party-lovin’, socially-adept, seemingly drunk Lockhart when I’m half asleep. Basically, my virtual tongue is a little too loose late at night.

I Never Know If The Receiver Is Mad At Me

Much like how the tone of my own messages may not be conveyed properly, I never really know how my receiver is feeling. Sometimes, I’ll receive an email, and it sounds harsh. Granted, the most likely situation is that they were attempting to keep everything short and sweet, but when it comes time to respond, I freak out. It gets so bad that there will sometimes be seven drafts of the email before it actually goes out.

4 Reasons I Feel Terribly Awkward When Sending Emails angry

So at the core, I simply just don’t know how everybody’s mood is when it comes to emails. Honestly, I think it would be best if everyone was loose and informal with everything. Who cares about professionalism? We’re all just people, right? (I’ll show myself out.)


Sending emails may not be my favorite thing to do, but it has to be done. There are dozens more awkward things that go along with this form of online communication, but that’s a little too much for now.

What other reasons make you feel awkward when sending emails? What’s the worst email encounter you’ve ever had?

Image Credits: solidphotopuravidaeliluna, anitapatterson

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