Internet Social Media

4 Reasons I Feel Terribly Awkward When Sending Emails

Joshua Lockhart 08-05-2012

4 Reasons I Feel Terribly Awkward When Sending Emails gmailAdmittedly, I’m a socially awkward Cringe With 5 Websites for Awkward Personal Stories There are several sites out on the Internet devoted to the publishing of awkward stories from all over. Some are kind of funny, and some are incredibly cringe-worthy. Moving right along the lines with sites... Read More 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 7 Best Websites To Find Weird News Weird news fills up the gaps and makes the world much more interesting. More often than not they raise a laugh or two. They do show that our world is a strange place, though not... Read More , 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 5 Tips for Ending Your Email Sending Anxiety Internet etiquette can be a touchy subject, and although I don't consider myself the Miss Manners of the world wide web, I try my best to be courteous with how I act online. Granted, I'm... Read More . 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 9 Types Of Facebook Status Updates That Your Friends Will Like One thing that I've noticed when I talk to friends that initially start using Facebook is that "nobody comments on my wall." Sometimes, I'll even try to help them out by letting them show me... Read More ? 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 3 Unique Android Alarm Clocks To Get You Out Of Bed Faster Getting up early in the morning is one of the most dreaded moments of the day for most of us. A cozy and warm bed, competing with dark winter days and cold bathrooms, doesn't make... Read More . 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 8 Ridiculous & Inconsistent Apple App Store Guidelines [Opinion] Here’s a radical opinion - you should be able to run any apps you like on the devices you own. Apple doesn’t agree, and it’s twisted itself into pretzels creating arbitrary rules for what app... Read More ? 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


Affiliate Disclosure: By buying the products we recommend, you help keep the site alive. Read more.

Whatsapp Pinterest

Leave a Reply

Your email address will not be published. Required fields are marked *

  1. Danni
    May 9, 2012 at 9:58 pm

    Great article Joshua! Thanks for taking the time to write it. Im in the people business too & totally get what you say although for slightly different reasons. End of the day, people matter, so taking a little extra time to consider how another person might recieve a message can go a long way toward producing healthy team environments :-)

  2. Lao Tzu
    May 8, 2012 at 7:50 pm

    number one my friend,
    please stop frequenting drive thru fast food places and join the real world eating real food, then I am sure the other problems will disappear.
    .good luck

    • Joshua Lockhart
      May 8, 2012 at 7:51 pm

      Working on it.

    • Mark O'Neill
      May 9, 2012 at 3:59 pm

      eat real food? Are you serious? Fast food is delicious! :-)

  3. zyzzyva57
    May 8, 2012 at 10:59 am

    An email is never completely deleted, so depending upon the other side's money and clout, think of a government agency, the more it can resurrect

    A good lawyer can twist an email into the opposite what you meant

    • Joshua Lockhart
      May 8, 2012 at 7:53 pm

      Anything can be twisted, I believe.

  4. Andy
    May 8, 2012 at 7:49 am

    I used to have some of these issues before I got a job where I would write email 4 hrs a day.

    The Tone Sometimes Seems Off
    - This goes away with practice. For starters you may want to mirror the recipient's style. They should be comfortable with their own wriring.

    My Jokes Aren’t That Funny
    - Don't joke. Really, joking is much better in person.

    I Send Emails When I’m Really Tired
    - I used to do that. Write them down at once and promise yourself you will only send them later.

    I Never Know If The Receiver Is Mad At Me
    -Seriously, you should care a bit less about this :)

    • Joshua Lockhart
      May 8, 2012 at 7:51 pm

      Nice tips, Andy. : )

  5. stonrdude
    May 8, 2012 at 4:27 am

    I find myself being too detailed on an e-mail. Instead of "OK, I'll be there", it is always,
    ok.. I need to do this, then this, then this too and then I will be there. Or a thousand reasons why I won't.

    It is self training to go back and use short, quick grammar, always tough for me. You don't seem like a guy too shy to buy TP, on the contrary, I thought you were quite outspoken. You must melt at the thought of picking up GFs BC pills or condoms! Yikes!!! Tell me, did you buy beer before you were 21? Heart Attack city Dude!
    Gads, did you ever need to get a motel room for a babe? Triple Yikes!
    Cool Blog today, Josh, Thanks, it made me smile.

    • Joshua Lockhart
      May 8, 2012 at 4:35 am

      Details, details, details... Too many.

      Ashamedly, I actually do have quite a bit of trouble with buying toilet paper... However, I can be outspoken when necessary. ; ) As for the lady, we're decidedly old-fashioned. However, even if there was a ring on it, I think it would be just as bad. Phew. Granted, there have been situations in which she has been with me while I am buying toilet paper, and she would make open remarks about it while in the store.

      Glad you liked the article! I'll try using the short, quick grammar. I actually had to send out an email today, and unfortunately, it became the eighth Potter novel.

  6. Anomaly
    May 8, 2012 at 2:41 am

    Wow must suck o give a crap what others think. I couldn't care less about some of the things that seem to really bother you. Try saying "screw you" when you start having some of those thoughts. It's very liberating.

    • Joshua Lockhart
      May 8, 2012 at 4:29 am

      Seems so, my friend.

    • Joshua Lockhart
      May 8, 2012 at 4:36 am

      Seems like it! Glad you're able to coast through, though.

    • Mark O'Neill
      May 8, 2012 at 5:48 pm

      If you couldn't care less, why did you read the article all the way to the end and then take the time to write a comment? It would just be simpler to close the page.

      • Anomaly
        May 9, 2012 at 10:59 am

        You misunderstand me. I meant that I don't worry or fret over the things that the author does. I didn't mean that I don't care that Joshua is having issues with them.

        • Mark O'Neill
          May 9, 2012 at 3:58 pm

          Apologies. It's often hard to understand one another on a webpage, when you don't see the person's facial expression or tone of voice. Which kind of proves Joshua's point about tone in emails. :-)

        • Joshua Lockhart
          May 9, 2012 at 5:57 pm