11 Awkward Things About Email

Email is one of those things that’s just a part of your life, period. Most of us know someone who has closed their Facebook account or refused to join in the first place in a little foot-stomping stand by their ego, and you might even know someone who is thrilled with themselves for not owning a smartphone.

But within the adult internet-using world, no one is allowed to not have email.

Not having email today would be the equivalent of not having a phone number—you’d have to be really doing your own thing to go there.

And so here we all are, typing things into compose windows, battling down our inboxes, and it’s going pretty well—but like any world of social interaction, email has its difficulties.

Let’s discuss 11 particularly awkward things about our email lives—

1) Exchanges that have an unequal power dynamic.

If someone you’re emailing with:

  • is making typos and you’re not
  • is skipping punctuation and you’re not
  • is skipping capitals and you’re not
  • is taking a long time to reply and you’re not
  • is responding to your long, well-written emails with much shorter responses

Then you’re their bitch.

Unequal email power dynamics can happen for many reasons—a professional ladder discrepancy, an age discrepancy, a “customer’s always right” situation, a thing where many people are all emailing one person—but usually, it’s that the person writing the high-quality email wants/needs something from the person writing the low-quality email. Simple as that.

2) Emailing with un-tech savvy Baby Boomers.

Not all Baby Boomers—you know who I’m talking about.

They’re the last remaining people with AOL email addresses. They scan a hard copy of an article and email it as an attachment instead of emailing a link to the article. They write the word e-mail with a hyphen in it. And they don’t know that “replying to all” is a thing that can happen in the world:

Sometimes, you’ll come across the especially un-tech savvy Baby Boomer who inexplicably writes their emails in all caps.

3) Emailing with anyone born before 1930.

To my grandmother, who tells me that her “machine is broken” when the browser window has accidentally been minimized, words like “forward” and “attachment” and “link” don’t have simple, concrete definitions—they’re just vague, complex ideas that she’s heard of but doesn’t understand.

She feels about email the way I feel about this sentence:

Central banks in developing countries are tightening policy and intervening in currency markets in response to concerns about the potential effect of currency depreciation on inflation, though gross issuance of nonfinancial corporate bonds and commercial paper have slowed and interest volatility has substantially diminished, possibly suggesting that reaching-for-yield behavior might be increasing again.

If you weren’t far too lazy to write a letter, it would be a good idea to stick to hand-written correspondence with people born in the 1920s, especially since there’s the side benefit that a letter from someone born in the 1920s will be a cool thing to own in 50 years.

4) The group email chain Late Responder.

5) Figuring out how to address a minor friend in an email greeting.

To make things easy, we at some point all agreed upon certain rules and regulations for how to address various categories of people that we email.

Notice the problem?

“Hi ____” is friendly in a distant, neutral, professional way for everyone you don’t know well. When your relationship with someone takes a step forward, it graduates to the warmer, more casual Hey Zone. And with really close people, you can just skip the greeting altogether—no one starts an email with “Hey Mom”.

But how about that green zone category of people who are more than acquaintances—so greeting them with “Hey” would seem too formal and distant—but you don’t talk to them enough to just out of the blue email them and start talking without a greeting? How the hell are you supposed to start an email to that friend from college you talk to every two years or that old work colleague you became friends with and then fell mostly out of touch with?

It’s not easy. And unlike all the other greetings, this one requires creativity. Some possibilities:

– Hey John! — The exclamation point says, “This isn’t a normal Hey greeting—I’m smiling and extra excited because we’re pretty close, and our relationship is a positive thing in my life.”

– Johnny! — A typical response greeting to the “Hey John!” email. It’s acknowledging that you’re on nickname terms, and also joining the celebration of your friendship with the exclamation point.

– Hey man — This is something guy acquaintances or minor friends do to deal with being in the green zone. It’s the greeting version of a friendly back slap.

– Sammmm — A girl tool to deal with the green zone.

– Heyyy — The extra Y’s say, “Just swinging by to say something, and we’re friends so sometimes we just swing by.

5b) Figuring out how to sign-off in an email to a minor friend.

Similar situation. For the distant people, we have all sorts of autofills—Best, Regards, Talk soon, Take care, Thanks, etc.—and the really close people need no sign-off at all. But for minor friends, we’ve got another whole song and dance on our hands.

I’ll sometimes finish a minor friend email with something like, “Thanks,” and then look at it and think, “Ugh it’s too formal.” I then sigh, put the cursor at the end of the word, and begrudgingly type in two more S’s.

It’s also worth noting that some people have decided that xoxo is an appropriate sign off because they’re just that adorable, and others just decided to start signing off with only the first letter of their name, because apparently we’re now dating. To me, both sign-offs make me think the person looks like this when they’re typing it:

6) Saying Robot Phrases, which reminds you that you’re not actually that unique a person.

A Robot Phrase is a commonly used email phrase that you end up using just because everyone else is using it and you’re not that creative a person.

These cookie-cutter Robot Phrases remind me of my voicemail recording being “Hi, you’ve reached Tim. Please leave a message.” The next thing that comes on is an actual robot that says “At the tone, please record your message yada yada,” and she and I are doing an equal job of expressing our individuality—but unfortunately, the only other option is to be an unnecessary weirdo by doing something surprising.

Email Robot Phrases are not quite as socially required as Voicemail Robot Recordings, but most of us are too lazy to deal with thinking up alternatives. Every single time I type one, though, I feel a slight twinge of self-loathing for being such a societal cog.

7) Mastering the exclamation point chess match.

With in-person interaction, we have a million subtle ways to express tone. Even on the phone, without the use of facial expressions or mannerisms, tone of voice gets the job done sufficiently.

But over email, we’re stuck with a crude set of symbols as our tools to express nuance, making punctuation a critical part of the email world. A few guidelines:

Some people don’t use exclamation points, and with those people, it’s safe to stick with periods.

Others use them constantly, and with those people you’re a huge dick if you don’t, so you’re forced to join the party.

This is important because to a rampant exclamation point user, the difference between a period and an exclamation point looks like this.

There’s also the rare but disastrous exclamation point / question mark mixup typo.

I can go either way with exclamation points and tend to just follow the other person’s lead, but I find that this is a pretty strong correlation:

Ellipses are a whole other thing. Some people use them to be mysterious or threatening, and of course, they can be massively slutty.

8) The epic correspondence that neither involved party wants to be a part of.

This is a very odd phenomenon unique to email. It happens when two not-that-good friends find themselves stuck in the mutually-obligated chore of writing long descriptions of their lives to each other every few months. Both parties dread having to answer all the last email’s questions and write a lengthy life description, and each is pretty bored by the process of reading the other’s.

This cycle either goes on until one of the people dies, or sometimes, someone finally gathers the guts to just not respond to the other’s email and then both parties can sigh a deep breath of relief.

9) Trying to shove the concept of laughter into the email medium.

Laughter is a delightful part of vocal correspondence, so we’ve decided we need to figure out a way to express the same thing over email—but it’s awkward.

Absurd people who say lol aside, here’s what we’re dealing with:

haha — I found this either mildly funny or not funny at all

hahaha — I found this a little funny

hahahaha — I found this reasonably funny

HA or HAHA or HAHAHAHA — I found this very funny

hahah or hahahah — I’m a very subpar human

At least in my world, I find that when something is actually funny, it’ll result in capital letters.

And in almost all of these cases, the recipient pictures the sender actually laughing as they type, when in fact they probably look like the guy in the picture above.

10) The fact that hurtful things are happening to you and you’re not thinking about it.

Being humored by fake haha’s is just the beginning.

You know how people sometimes BCC someone on an email they’re writing to secretly loop them in? You know what you don’t consider? The times when you’ve received an email from someone and there’s a BCC happening unbeknownst to you—when you’re the chump being spied on. Kind of upsetting right?

How about the fact that you’re part of a number of group email chains, some one-time things and some that are recurring—and you kind of just assume that those are the only group chains happening. When in fact, there are a number of group chains between various friends or family members of yours that you are not included on, whose existence you never really consider.

Worse, think about a time you’ve forwarded an email you received to someone else for mocking purposes. Kind of mean, but you’ve also kind of done it right? How shitty is it that at some point, you’ve been the subject of the secret mocking forward?

Luckily, we tend to avoid assuming these things are happening. But they’re happening.

11) Email disasters.

The email disaster is a special kind of disaster. It can be mortifying, hurtful, or even friendship-damaging.

Examples include:

– Emailing Person X to say something bad about Person Y and accidentally emailing it to Person Y instead.

– Replying just to Person X on a group chain to say something private and accidentally replying to all.

– Forwarding an email to someone and forgetting that below the email is a whole correspondence chain that has something sensitive in it, maybe even about the person you just forwarded it to.

– Sending an attachment to someone and accidentally attaching the wrong horrifying thing.


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More examples of life being awkward:

The Great Perils of Social Interaction

10 Types of Odd Friendships You’re Probably Part Of

Why You Secretly Hate Cool Bars

And this is what happens when someone takes too long to respond to an email I write them.

  • Wow, this post worth the waiting, it’s huge, I’ll leave it for later and read it in my other black playground

  • Anonymous


  • Anonymous

    I’ll just print this out so I can read it

    • Jenn

      I had to print it twice because I lost my first copy… Hahahaha!

      Maybe you found it? x|

  • Anonymous

    I BCC my spouse on a application/cover letter to a job. He replied all (habit from work) with Fuck that guy, he has a douchey name.

    • Steph

      This would happen with my spouse. I actually burst out laughing at this.

    • Two Rules

      Yep. I have two related rules.

      1. Never BCC; always FYI forward. BCC recipients too often accidentally or deliberately chime in, exposing the BCC’er (you) as secretive and potentially manipulative.

      2. Never send anything you wouldn’t mind becoming known to anyone. You have no idea what a recipient would do with your note. Pick up the phone for relaying snark.

  • Anonymous

    forwarding a message to someone to complain about the content in the original message, but accidentally using “reply” instead of “forward”.

  • Anonymous

    This was the most enjoyable read ever in the world.

    • Anonymous

      I agree. I am telling my Gran about it.

  • HAHAHA – WBW strikes again. Good one, Tim!

  • Matt

    Those drawings have me pissing my pants. Best one was the last one.


  • Anonymous

    You described my baby boomer mother to a T. AOL, e-mail with a hyphen, never replying to all. It’s funny that that’s a “category” of people, not just my mom.

    • My dad is exactly like that. I laughed so much I had to leave my desk at the office.

    • alan

      then there’s the people that “reply-all” to everything – when those of us on the cc list were there by courtesy and could care less about side conversations.

  • Anonymous

    HAHAHA. I work for a #2.

  • good articel

  • Anonymous

    I think I use too many exclamation points. I love that you capture what we are all thinking when we send emails… (slutty or trailing off? You’ll never know.)

  • just sent it to everyone i know…

  • I wrote a short one line email telling my future husband he was the “love of my life” accidentally sending it to another person in my email address list with the same first name – a work colleague.

    • Anonymous


    • Natasha

      Pam, I did basically the same thing, but it was a long, reflective, bit about what an impact meeting him had had on me–sent to the wrong Michael.

  • Anonymous

    I didn’t have a printer at home and sent a quick email with attachment to my boyfriend: “hey babe, can you print this?”

    The reply was instant: “?????” And then I realized I had emailed my old stick in the mud boss instead. I hope he laughed it off after my apology/explanation, but I couldn’t be sure. Damn autofill!

    • Anonymous

      A nice thing to try in place of laughing with “haha” is to use a variety of different words in asterisks to denote an action. For example, try something like *chortle* to indicate a chortle like laugh, or the desire to have chortled at the posted text without having actually chortled.

    • Or complete stage directions. *laughs like elephant in heat while walking backwards*

      • Jenn


  • Anonymous


  • Not a nightmare scenario as such, but a nightmare category I call the ‘heat seeker’. This is the special type of person in the workplace – and you can SEE them do it! – who send you an email and then get up and walk over to you and hover over you saying “did you get it?” “Get what?”, I say knowingly. And then you pretty much sit there while you wait for their email to land – meanwhile they’re having a good look at your inbox. You open their email and they read it out to you.

    I mean, seriously..?!?!

    • Anonymous

      haha. I found this either mildly funny or not funny at all.

    • Anonymous

      YES. I work with a person just like this and cannot begin to use enough swear words to describe incredibly annoying it is. It’s a total time suck. This particular colleague composes the email, sends it, comes around the corner to my office to inform me that they sent an email, waits for me to read the email, and then stands next to me to discuss it…………….. AND I then respond via email to maintain documentation of any decisions made. Oh, and whatever I’d been working before this debacle, is completely abandoned mid-thought/sentence while this stupid charade goes on. Not that I’m bitter about it or anything.

    • Anonymous

      I have a co-worker who does this CONSTANTLY. I’ve now learned to say “Nope, didn’t see it yet, I’ve got about 100 emails that I haven’t read yet. I’ll let you know when I get to yours.” And then I turn my back to him until he goes away.

      • alan

        good approach; rude doesn’t get special consideration from me.

    • saraj

      My past office job: http://www.theawl.com/wp-content/uploads/2011/11/Office-Nemesis_edit3-3.jpg

      Except he wasn’t my Nemesis, he was my boss. No cats on the wall, just biblical images. No nemesis-in-training, just me to get 100% of his attention. He tried to set me up with ‘nice young men’ form his church when I already own a house with my boyfriend, whom he had even met at the Christmas party (NOT holiday party). I started a twitter account just to vent about him. I jumped ship after 4 years and have been so so so happily self-employed since.

  • Anonymous

    My God number 1 is so spot on. I have been in that position so many times that I finally stopped giving a shit about being too polite.

  • Anonymous

    You neglected the “Aa First” laugh: Aahahaha! Adding an A or two in there before the haha really seems to take the laugh up a notch. Otherwise, so spot on!!

  • I always use “haha” and never in caps. I still use “Lol” for special circumstances (when something is truly funny ;))

    • Anonymous

      Yup. Same here. Always lower case “haha”, never anything else, regardless of my actual level of amusement.

  • You are seriously good at what you do. I’m going to print this out, scan it, and send it to all my friends.

  • Anonymous

    Referencing number 5 here. I hate people who start emails with “Hi”. I especially find it weird in a professional setting. Just put their name and a comma. You can use this with any of your four groups. Done.

    • Anonymous

      Actually, a lot of people find that somewhat abrupt if not rude. That said, it’s used a lot in the business/professional world. The old standby (throwback? 🙂 ) “Dear” is probably best for more formal correspondence.

    • Anonymous

      I personally find “Dear” to be antiquated and even jarring. In all my correspondence, I almost always use “First name,” or “Hi First name,”. Very occasionally I will just do “Hi,”. Most people use the same introductions on their emails to me. I’m not sure where you get the idea that a lot of people find that abrupt/rude, but I certainly don’t and there is no indication that my email correspondants do either.

    • Anonymous

      What happened to Hello, _______, ?

    • Nee

      Mine is usually a good morning, afternoon or evening and the name with a comma. Professional yet considerate.

    • Anonymous

      I disagree re: listing names, for me it brings up pecking order questions, I’m always afraid someone is going to get offended that I’ve listed someone else’s name first. There’s no good way to do it that I can think of. I do a “Hello everyone” or “Hello all” or something similar depending on the group.

    • Anonymous

      I don’t mind ‘guys’ but sincerely objected to ‘Gents’ as a group email greeting.

    • Anonymous

      I don’t know how old you people are, but I’m a college professor in my 30s and I find it ridiculous when students address me with “Hi” the first time they are contacting me. It’s not cool. I never do it when I address them or others (professors or otherwise). The first contact should always ALWAYS have “Dear” when you don’t know someone. Email is not a face-to-face conversation. The first exchange is like a letter, and some respect is necessary. I refused a student into my class once because her first email just launched in: Hi, I’m on the wait list. I would really like to take this course. etc.

      Sounds like entitlement to me. I thought the whole graphic above about hi vs hey missed the ball on this. And of course, I am not alone. I’ve talked to several people about this. Maybe amongst rising teenagers this might change. But so too will spelling out words (u vs you). So if you’re a teenager in this comment section just know that you won’t be scoring points with those older than you anytime soon if you stick to the hi and hey convention.

      • Anonymous

        You’re only in your thirties and are this behind? Literally no one uses “Dear” in emails, ever. You’re a professor and you’re still approaching language in a prescriptive way. Tsk tsk!

        • alan

          Not quite “literally” true. In a business first contact with someone you don’t know at all, i.e. very formal, “Dear…” may be appropriate. Depends on the business you’re in. If I do use it, the rest of the email is likely to be a bit formal / almost stilted, too. If they reply less formally, that’s a clue to follow the lead.

      • Anonymous

        Are you an English or PoliSci professor? I ask because my former professors and (now that I’m older) my friends who are professors (physical chemistry, molecular biology, human genetics, neuroscience, game theory, analytical chemistry) don’t care for “dear”.

      • haha guy

        Dear Professor in 30’s
        Hope your class evaluation is bad. It is incredibly arrogant to deny a class seat to someone based on their initial email. You are an educator and should have taken this opportunity to educate that student after allowing them to join the class, all other things being equal on the wait list protocol.
        – Decidedly non-academic,
        Guy in 30s

      • Anonymous

        Being from France, where everybody is more formal in correspondence, but teaching in the States, I HATE when my students Hi or Hey me via email. I do have to remind them all the time to use Dear… And end with some “Best” or whatnot.
        Maybe I do sound uptight in the rest of my correspondence, but I would say I would rather sound too polite than straight up too cozy. Nothing worse than being too cozy and then getting a somewhat cold and formal answer.
        Actually, because I am almost my students age (I am a 26yrs old TA), I take their emails rather seriously, otherwise they really don’t take me or anything I ask them to do seriously. That being said, I am pretty laid back in class, but I really don’t want them to think we are friends because we are just not.
        When a student thinks you are cool, you have to deal with so much more bargaining and TAs know there is no time for that.

        • Jamie

          So well thought out, especially the last sentence!

    • Anonymous

      I’m a 52 year old university professor, and I don’t see anything wrong with initial emails from students that say “Hi, I’m on the waiting list..”

    • Anonymous

      At my company, everyone uses Hi, name, in emails.

    • Anonymous

      I’m also a prof and get all sorts of greeting– and I’m fine with any of them. What I get upset about is the messages that are dashed off without any editing and are riddled with spelling and punctuation mistakes. You’re in an English class, right? You better figure your professor cares about language. Think about audience, please.

      • alan

        Agreed: always think about your audience – written or spoken. Worth the effort, if your intent is for them to understand you. Not so much if you’re just talking to hear yourself…

    • Anonymous

      That is Quite Funny

  • Anonymous


  • Have you ever read the garbage articles on the “Wait But Why” blog? I’m not sure if they are supposed to be funny or serious, but they all read like 2nd grade book reports complete with stick men. I highly recommend you don’t subject yourself to ever visiting that site.

  • Oh god! That was totally supposed to go on another comment section.

    • Well done Slytherin. Well done Slytherin.

    • Anonymous


  • Anonymous

    I was Greg once. A nasty little email where my former roommate described in detail why she couldn’t stand my boyfriend spending time at our shared apartment. This email was sent to my entire group of girlfriends. I think the picture of Greg should include Greg looking like he just got punched in the stomach.

  • Anonymous

    I love this! Please do one on text messages!

  • Anonymous

    My younger brother accidentally included my mom’s and my email addresses when sending a late-night drunken missive to his college roommates all about his latest sexual conquests, full of macho braggadocio and unnecessary sexy details. Really wish I hadn’t seen that one.
    As for myself, I’ve “recycled” letters to various friends — acting as if I were writing a thoughtful, newsy email solely for that person — only to have one of the recipients reply to me with the original included, cc’ing everyone else in the group, thereby showcasing my laziness and mild duplicity to everyone who thought they’d received a unique letter. Certainly not the worst that could happen, but yet another email peril!

    • Yeah good one. I’ve both gotten caught doing that and caught people doing that. It shouldn’t be a big deal but it kind of is.

  • Anonymous

    So was I the only one who copied “schadenfreude” into Google in the hope of being enlightened? (thank you wikipedia!) and BTW, thank you Facebook for giving us a heads up before we post a comment with the red underline! bwahaha 🙂 Bel

  • Anonymous

    You forgot the amazing work email when you write a perfect email describing your master piece, but you forget the attachment. So, you go home happy with your job done and you realize that next day :/

  • I’m brazilian, so I laugh hauauhauhahauhua

  • Excellent post, btw!

  • Anonymous

    My baby boomer Dad will only reply to polar questions via text message or email.
    Also, in Australia a very common email sign off (regardless of familiarity to the recipient) is “Cheers”.

    • David Spector

      What is a “polar” question? Never heard of that. I’m thinking, something about Antarctica, which might be a well-known vacation spot for Australians?


      • Allison

        PFFFFFFFFFTBWAHAHHAHAHAHAAAA!!!!! heheheh lol. oh yeah. Khhhhh.
        And I mean every word of it.

    • Anonymous

      A yes-no question.

    • Jenn

      Yes, we are very fortunate with cheers aren’t we?
      I work outside of Australia but there are a few Aussies around in my industry and it is quite common to end correspondence on the 2nd, 3rd times with Cheers.
      I like it. It’s friendly!


      • alan

        Used to get emails from a Brit (sales rep for our company) that signed off TTFN (meaning Ta Ta For Now).

  • Anonymous

    There is one category 11 I think you left out – intentional e-mail* disasters. Maybe an 11b, eh?

    As a grad student, I was in a national political geography list-serve – at the time (90s), the list-serves were still kind of new and people didn’t really control them well. (note to the kids: these were the tweets of the nineties, essentially).

    So, about five times a week all of the political geographers in the country (professors, students, lecturers, non-academic followers, etc.) got an e-mail about what some political geographer was doing or some meeting that was being organized. Well, at some point, person A crossed person B, leading to person B writing to person A, in a *private* e-mail, “…well you don’t have to be a f*cking c*nt about it.”

    Not a very professional or academic thing to write. So, the recipient of the c-bomb, person A, responded *TO THE ENTIRE LISTSERVE* with a nice little passive-aggressive response like “well, you don’t have to be rude about it,” and including all the private correspondence in it. There might be 300-400 academic political geographers in the county; it’s not a huge group of people and if you want a job in the field, it’s not super swell to have all of them read your nastiness. Ouch…

    * (PS: I am not a baby boomer, but rather a strong believer in hyphens…)

    • Anonymous

      Yeah, this type of passive-aggression happened JUST LAST MONTH in a Google group I’m in (of environmentalist women, if you can believe it).

      • anonymous

        no offense whatsoever intended as i love anyone who would describe themselves as an environmentalist woman. but it is extremely easy to believe that passive-aggression is prevalent specifically amongst environmentalist women, there are few other types of people i would expect to be less passive-aggressive.

    • Amazing story. Person A comes off worse, but it’s also kind of an awesome move.

      I’m also disappointed at the lack of details in Anonymous #2’s story.

  • Anonymous

    Thoughts on Forwarding etiquette?
    You have an informal private email chain with a professional contact who then decides to ‘consult’ everyone else at work by forwarding your informal, misspelled, non-capitalized opinions to the whole office.
    OK or not?

    • Anonymous

      Ugh, that frustrates me! NOT OK. At work, I’ve just decided anything can be forwarded at any time and try to make everything professional-quality. Which obviously takes up most of my day. SIGH.

      • Jenn

        Perfect time to resort to another antiquated form of communication – the telephone!

        I’ve found it generally hard to have this forwarded 😉

    • alan

      Not. You don’t forward private stuff without the ok of the originator. Just offensive.

  • Anonymous

    Email disaster – matt wood (friend), matt woods (client), not paying attention to dropdown contact list… you can figure the rest out.

    • Anonymous

      My boss’s wife was Sandra and he emailed me Sa—– instead of her quite often. He also wrote whole emails in all caps in the subject line.

    • Bart

      yes, I was also thinking of this one. I’ve got it a lot. Send to bart! some minutes later. Oops sorry Bart this mail was meant for another Bart.

  • Ryanne

    Someone sent an email to a wrong distribution list, and followed by hundreds email replies with “PLEASE DO NOT REPLY TO ALL!!”

  • Anonymous


  • Anonymous

    Category 09: What about “lol”, “lmao”, etc. ?

    • Anonymous

      Yeah, I agree, what’s wrong with lol? It’s so much simpler than having to figure out exactly what form of onomatopoeia to use.

  • Anonymous

    I’d like to add No. 12

    Those that come into your office immediately after sending an email to say “I’ve just sent you an email” !! HaHa

    • Bec

      Or in a shared office – “I’m just sending you an email about xyz” while they’re typing it! Seriously, you cant just turn your chair around and have a conversation with me?

  • Anonymous

    Email accidents – In the heat of anger, sending an email to my boyfriend saying “my boss is such a fool, he has no idea what he is doing”, sending it to my boss not my boyfriend… Then having to do the walk of shame to my bosses desk to explain why he was a fool, why I needed to tell other people that he was a fool, and how I thought I could do things better…

  • Anonymous

    Whatever happened to good manners? This is just so precious. How to greet and sign off in written communication was worked out a long time ago – way before Baby Boomers. Sure, things have progressed (a little) and it is possible to be casual and a little ironic but this is a manual for navel gazing. This internet generation is so inside itself it has forgotten how to look outward and not be so damn self-conscious.

    • Anonymous

      No time for that. 100 more emails to answer.

  • Anonymous

    “Central banks in developing countries are tightening policy and intervening in currency markets in response to concerns about the potential effect of currency depreciation on inflation, though gross issuance of nonfinancial corporate bonds and commercial paper have slowed and interest volatility has substantially diminished, possibly suggesting that reaching-for-yield behavior might be increasing again.”

    You probably should figure out what that means and understand it.

  • Anonymous

    #1 drives me especially crazy because I’m a good typist with fairly decent spelling, grammar and punctuation, and sloppy emails are seen as somehow more youthful and breezy and cool. On occasion I have actually resorted to inserting a typo or two on purpose just to avoid coming across as too Little Miss Perfect.

    • Anonymous

      Me too! I’ve also done that when I don’t want to seem like I care *too much* about a particular email chain, when in fact I do!

  • After read the article, it is almost an obligation to spend sometime on the comments too….hahaha…hilarious!

  • Kim

    It didn’t happen to me … but one morning I arrived at work to find that a chain mail had gone around the world (70k employees) in our organisation with this list of Indian names (we had a large Indian presence) and in the middle one western name stuck out with “gee this is fun” as the message. I looked up the western name in the directory and it was a graduate development student – not the best way to impress your boss there.

  • Anonymous

    Haven’t seen it here but my “grist” is with people who “love” to “sprinkle” the “quote” symbol around “random” words all through their “emails”. WTF, man? What kind of weird “effect” are they trying to “make”?

    I always appreciate a WBW email every Tuesday! Thanks, Tim.

    • Anonymous

      Yes! People use quotation marks for emphasis, which drives me crazy. Use italics, bold, or caps or *s with plain-text. But quotation marks mean something different entirely.

      • A Non-E-Must

        SO TRUE!! quotation usually means something sarcastic or fake (e.g. her “awesome” performance means that this her is bragging about how great her performance was but the writer of that sentence puts quotes around it so he dislikes her performance)

      • Unfortunately (unless I’ve missed it?), Bold, underline and Italics aren’t available in FaceBook comments – so the only options for emphasis are *asterisks* and “quotes” or ‘singe quotes’.

  • Anonymous

    My mom was born in the 20s and unfortunately almost kind of sort of knows how to use email but not very well. She can’t see very well so she likes to print every email, then she leaves them lying around the house so everyone can read them. She also doesn’t know or notice that the whole email conversation will be printed along with her email, and this can lead to some awful and hurtful things. The worst was when I emailed her the name we chose for my new baby, and she left a print of an email she’d written to someone about what a bad name it was and how she hated it on the kitchen table. She’s known for her tactlessness anyway but email has made her supersonically so! Thanks for the great article.

    • Anonymous

      ouch!! but maybe don’t read things laying around the house?

  • Anonymous

    How about when all you want to do is share a link with someone (say, to a hilarious blog post such as this one) and don’t really have anything else to say. But in this day and age, you can’t just send someone a random link or they’ll avoid it like the plague … (or a virus). So now I’m forced with coming up with creative ways to make it obvious that yes, the real me (and yes, I’m clean!) has something interesting to share with you!

  • Google Labs has a nice feature you can add, where you can recall e-mails after you hit send– of course, it’s only helpful if you catch your error right away. There have definitely been several times when I’ve sent an e-mail without an attachment, forgot to CC someone and had to type up an entire follow-up/apology/explanation e-mail as a result, etc.

    And yes, I’m in my twenties, but I still use the hyphen in “e-mail.” :-/

  • Anonymous

    What a load of crap. I use email every day and it is not awkward and people on the other end don’t feel like my bitches because I can write well or have a better vocabulary. Only some Gen y moron would make up this garbage and only some Gen y moron would read it and agree…. Gen y, the 21st century morons!

    • Greg

      you, good sir, missed the point entirely. …completely flipped what he was saying.


    • Nate

      You have it backwards. The article is saying that the person whose email is more formal is the bitch of the person using a more casual style. So, you would be the one feeling like their bitch.

      • mccmomof3

        But he obviously doesn’t; I think he’s just saying it doesn’t matter…some of us can write a polite, well-written email in the time someone else can type the two-word one! Everything doesn’t have to have hidden meanings.

        • alan

          In general, it’s a waste of your life trying to figure out hidden meanings!

          • durrr

            gen z here, i almost never use my email. i don’t even have a Facebook cuz gen z thinks Facebook is 4 old ppl lol instagram 5eva like lol

  • I think you brushed over the overuse of ellipses and the confusion they can cause…


    Also, I second the cry to do one of these about text messages. My mom signs most of her texts, “Love, Mom” and has recently discovered emoticons.

  • Anonymous

    There’s also the auto-correct mishaps. I had sent an email to a patient wanting to say that I left you a v/m (voice mail), but instead the auto correct sent it as I left you a BM.

  • I’m a Boomer. It’s true that I can identify fellow Boomers if they have an AOL email address. Now that I do swipe writing on my mobile device, I’ve jettisoned the use of the hyphen in email. However, I still use words like jettison. ROTFLMAO

    • Anonymous

      Late response! HA

  • Christa

    I actually do look like 5b and sign personal emails xoxo C
    so awesome

  • Alex A.

    The reason the person that emails ‘Hilarious!’ with a big delay is awkward is because his response time implies that he is busier or has more serious things on his or her mind than the rest of the email’s recipients.

    • alan

      …and maybe he is, or does. Neither email nor texts really have to be answered immediately to avoid showing offense. Gotta be careful not to let them take over your life.

  • My godmother uses a lot of butter when she makes mashed potatoes. She once met the King of Belgium at a fancy ball.

    • MammaG123

      Good on her.

  • Anonymous
  • A.S.M.Rao

    I am an octogenarian.With lot of difficulty learned how to send an email.After typing a full page
    letter, I clicked a button and was surprised that the whole matter disappeared.

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  • Darcilyn

    What about Bwahahaha ? What does that type of laughter written say about me?

  • Matt

    One of my biggest peeves is when someone forwards you a running email conversation they have been having with someone, wherein lies some nugget of info that you need – but you have to scroll down through several unrelated emails to get to it. I call this the “Picking through a pile of elephant dung to find a peanut” email.

    One thing I have decided about these types of emails is that once you have forwarded this mess to me, I am authorized to contact any of the listed correspondants directly and bypass you – something you may not always like.

    Oh, and I (53 y.o. boomer) am often aghast at how email-clueless many Gen X and Y people are.

  • Patrick

    In a bit of an email chain with old school friends from Ireland, we’d generally email during work hours. So, LOL’s were pretty out of the question, not to mention ROFL, LMFAO etc. I generally steer away form the old lol, and when I receive it very much doubt there is any actual laughing happening at all. So we developed LSCTOWNEIL (Little Sly Chuckle to Oneself While No-one Else is Looking) It’s just so much more honest, and after a while it resembles more than just a bunch of random letters.

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  • Susan

    What? I’m a baby boomer, what are you talking about?

  • wobster109

    It would be very nice if you didn’t use words like “slutty”. That’s a women-hating word. It’s condemning women who write sexually-suggestive emails, and that’s unfair.

    Perhaps you could say “flirty” instead? Using ellipses can come across as flirty for all genders.

    • alan

      BS – Not actually the same.

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  • Leila

    If you worry about all these small things, then you really not busy. A professional email i believe should be respectable and polite and phrased correctly. On more than one occasion,people just don’t have time and as long as the message is out, i really don’t care much.
    There are too many other important things to care about then how you were addressed. I really don’t mind if its a hey or a hi or a dear. I think the dear is a bit much of a muchness! At least the person responded.
    I think people should wake up and stop being selfish.
    The fact that you read the entire 11 or 12 steps, proves that you really do not have much work to do that’s why you can worry about grammar and punctuation etc..
    Get real!

    • MammaG123

      If you can’t be bothered to use proper grammar and punctuation, don’t be surprised when people think you are unable to use proper grammar and punctuation. Command of the language is a prerequisite for most jobs.

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  • Trumpingham

    I like to open an email with the phrase “In the morning!”, as per Adam Curry and John C Dvorak in the “No Agenda” show.

  • Suraj K.C

    I have just save it on word file. really hope to help me in future…….

  • Anonymous

    A friend wrote this having read the blog.

    “5) Figuring out how to address a minor friend in an email greeting.”

    I still can’t figure this out, and often end up over-thinking it, and even changing my greeting just before sending the email, weighing up the audience or recipient.

    Moving between roles in company, I’ve noticed clear differences in approach to it. When I was on the engineering side of the business, people never used “Hi Kevin”, just simple straight forward “Kevin”, and I followed suit. But since going to the marketing & sales side, it is all “Hi Kevin”, and I feel obliged to follow suit. So you’ll have email conversations with people you work with all day, back and forth in space of 30 minutes: “Hi Kevin”, “Hi James”… “Hi Kevin”, “Hi James”… “Hi Kevin”, “Hi James”… It’s just silly. And it’s not like the marketing guys are any friendlier than engineering side, the reverse is the case in fact.

    I preferred the engineering approach, less messing about with meaningless shallow greetings all day, and you didn’t have to think about it, and second guessing the use of “Hi”.

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  • anonymous

    I had a “friend” of 12 Years that I found out was a whirling dervish of a narcissistic psychopath AFTER I gave him my money. When the venture started coming apart I realized everyone was being manipulated and told a different story… that the first order of business was to take his talking stick. I plummet the old emails and found that early emails were sent out CC instead of BCC. Got twelve people together in the plaintiff group and WON the case.

    Email snafus aren’t always bad.

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  • Anonymous

    Stereotype much? My grandmother and her friends–all in their 80s–are very web/email competent. Hell, grandmom built a computer herself a few years ago. Now, she’s using a laptop and tablet, of course.

    Also, if you email me with my first name before we’ve met, I assume that you have no manners.

    • alan

      Or you might assume your new correspondent had no other reference for you? Or was simply trained to believe formal naming conventions in a semi-formal medium send an off-putting message of unfriendliness, i.e. what you would receive from the IRS or a plaintiff’s lawyer. I don’t think I’ve seen an initial email starting with “{Greeting} Mr {Lastname}” in years, whether business or personal.

  • OldPhil

    What a dick-head. Notice I put a hyphen in there?

    • bbroome62

      We need a million man march on the Mall to reinstate the hyphen. And while we are there, insist that Pluto re-gain it’s status as a planet.

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  • David

    *meh* Written by someone who hasn’t been using email for more than 35 years.

  • Dirtman

    Instructions like these have been circulating for twenty years or more… It’s about knowing how to communicate to influence rather than wallowing in your self-importance. It’s also about learning through discovery that your boss really does not have time to read your detailed message (or reply in a detailed fashion) and that your team mates don’t respect you (or whomever is the team leader) enough to read it, either. Good e-communication takes experience. If you’re dealing with customer service you tell them exactly what the problem is – you want that problem solved and that’s it. If you’re trying to convey detailed instructions or a record of a decision, etc., provide a summary sentence at the top – for the boss – and then a message to the rest of the team that a) please read the entire message, or else – yep, they’re kids who need to be told , and b) be readable. Finally, since it didn’t work back then it doesn’t work now: use plain text for all e-mail communication. Why? Because everyone’s settings are difference and what is more frustrating (context) than a co-worker who you needed to read that important (yes, it was!) message telling you “I couldn’t open those links you sent/the paragraph numbering didn’t show up/etc.” That is all.

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  • Debbie Irwin

    This is a topic I’ve been wanting to write about for years…
    Countless times I’ve responded to an email with no salutation– in much the same way you converse in a conversation without saying the person’s name before your speak– only to reread the email before I send it and add something in at the top so it feels proper.

    I think that the amount of time that elapses between the back and forth plays a big part in whether or not a salutation seems appropriate.

    Sincerely (a word I NEVER use in an email),

    • MammaG123

      I do the same thing. I suppose that’s a nuance between a “mail” type of correspondence and a chat-like exchange. After I compose the body of my emails, I go back and add a salutation. It always feels forced.

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  • LaloTweets

    ay caramba!

  • Dav

    How is laughing with ahahah or ahahahah finishing with an H mean you are a subpar human?

    I’m laughing online since 1998 and i garauntee you that’s 100% normal.

    When i’m just answering to some mildly or not-at-all amusing joke i simply put a “lol” or a “XD” to shorten things up if i don’t want to offend the other part, if i want to i just use a -_-‘ or something like that to make him notice.

    When something is kinda funny i just press a random amount of times the letters “a” and “h” which results in something like : ahaahahha or hahahahahh or ahahhahhaaah or i don’t really care.

    When something is actually really funny i do the same thing in CAPS

    It’s just the “emotion” of laughing that should makes you type a random amounts of A and H in a random order without really checking how many of them you typed and in which order. Typing a determinate “ahahaha” or ahaha” checking both the order and the amount of letters just seems utterly cold and stupid to me. It should be a spontaneous laugh after all and all the effort you can do to make it seem slightly more real is to put some randomness caused by the emotion in it. You’d better go for a rofl or a lmao otherwise.

    • bbroome62

      I’ve gotten replies on social media where the respondents claimed to have pissed their pants.
      Is their a character for that?

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  • It’sStoryTime

    SO, I try to sound enthusiastic and cheery in mails, and as I was reading this, I opened up my email conversations to analyze. AND EVERY SINGLE ONE OF THEM ENDS IN AN EXCLAMATION POINT. AND…A SMILEY. I now understand what people mean when they give me weird look as they say, hey, I got your email/reply.
    How on earth did I miss that? -_-

    • MammaG123

      I am also guilty. I thought I was being all sunny and positive, but I am so glad I now can see it from the recipient’s point of view. I’m so annoying! 🙂

  • Keenan

    Greetings! I know this is kind of off topic but I was wondering if you knew where I could find a captcha plugin for my comment form? I’m using the same blog platform as yours and I’m having trouble finding one? Thanks a lot!

  • Laurie Larks

    You had me at ‘If you write a nice, well-expressed and properly punctuated email, and the recipient replies in five typo-ridden words… you’re their bitch.’ My life as a freelance writer summed up in one neat observation! Also love your stick figures, their fraught lives and expressions.

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  • Vincent

    Awkward Email #11 – Email disasters.

    Recently at work, one of the department managers hit reply all instead of the specific person (another department manager) he wanted to reply to. We ALL saw the email in which he big noted himself and berated and put down the other manager. He’s a total dick and his email reflected that. It was so unnecessarily rude and bullying.

    But that’s the way is goes with bosses, yeah? Shit floats to the top of the tank.

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  • anonymous

    ummmm ok .-.

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  • Fred Arthur Tenzer

    Stop branding people who are not out to harm anybody and have never threatened anybody as stalkers, cyberstalkers, and/or harassers.
    The laws on stalking, cyberstalking, and harassment ought to be changed so that worrying about someone, seeking a reconciliation with someone, etc. do not constitute stalking, cyberstalking, and/or harassment. The law ought to state and rule that if you do not want someone to contact you, you must tell the person so directly instead of (1) reporting the person to the police and/or (2) having someone contact the person on your behalf, because these things are despicable and extremely rude. Also, regardless of whether or not it was you who initiated email or other contact with the person in the first place, you ought to be required to tell the person what the person did wrong that you no longer want anything to do with the person in the first place in order so that the person will accordingly (1) undo whatever the person did wrong to you and (2) make amends for everything that the person did wrong to you.
    The law also must require that peace be made between all people who have ever contacted each other through email and/or any other means.
    Please create and pass a law that makes it illegal for the police to keep files on people who are not out to harm anybody and have never threatened anybody. In addition, people who are not out to harm anybody and have never threatened anybody should not be jailed, arrested, or in any other way punished for stalking, cyberstalking, and/or harassment. The laws ought to be changed so that if someone sends you several emails but you do not reply to any of the emails but you do not tell the person who sent you the emails to stop contacting you, the sender of the emails cannot be imprisoned, arrested, or in any other way punished for stalking, cyberstalking, and/or harassment. If you do not want someone to contact you, you ought to be required to tell the person so directly instead of (1) reporting the person to the police and/or (2) having someone contact the person on your behalf for these kinds of things are despicable and extremely rude. It thus ought to be illegal for the police to keep files on harmless people whom someone accused of stalking, cyberstalking, and/or harassment, for this violates people’s privacy and gives them an unjustified bad reputation.
    Furthermore, imprisoning, arresting, and/or in any other way punishing harmless people diverts police manpower to the wrong person, thus making it impossible for the police to protect people from those people who are actually dangerous. It is thus wise to make peace between people who have ever contacted each other through email or any other means instead of punishing harmless people.
    Please reply.

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  • While writing a cover letter for a dream job application, I accidentally hit SEND even though the letter was still a rough draft full of typos and run-on sentences.

    *ugh* Guess who didn’t get the job.

    Lesson learned: Put in the recipient’s name in the box AFTER writing the desired letter.

  • Tom

    HAHA. I had my smartphone read this post to me – it’s hilarious how the computer acts out the different “hahas” of paragraph 9 🙂

  • Matthew Barnard

    HAHAHAH this was great hahah. I like to think about what I want to send for 5 minutes before I actually send it. Saved me from some embarassment.

  • Michael

    An article written by an older guy would have dealt with the topic of “top posting.” Before Windows 95 came out with its default email client, everybody used to write emails like this:

    > What did you say was the meaning of life again?


    > Also, how much wood could a woodchuck chuck if a woodchuck could chuck wood?

    Again, 42.

    Joe Bob McGhillicuddie

    After 1995, everybody gravitated toward “top posting,” because Outlook Express didn’t let you cut up the reply text into chunks, and it positioned the edit cursor at the top of the message. Soon, emails started looking like this:

    I’m sorry, I don’t understand what the number 42 has to do with anything.

    > 42.
    > Again, 42.
    > —
    >Joe Bob McGhillicuddie
    > >
    > >
    > > What did you say was the meaning of life again? Also, how much wood could a woodchuck chuck if
    > > a woodchuck could chuck wood?
    > >
    > > —
    > >Jimmy Joe Simpson

    Jimmy Joe Simpson

    To those of us who were online, because online was just damn cool, the world was never the same again. To most of you who got online since then, you have no more idea what I’m talking about than someone born before 1920 understands what a video codec is.

    After holding out for a decade or so, I finally started adapting my style to suit the times, and I “top post” with strangers, and even less enlightened friends, but I still use the correct method of editing the reply text and interweaving my reply into it when I’m dealing with guys who are old enough to know better.

    I almost never use greetings or closings with anyone.

    It annoys the shit out of me to write a poorly-composed message, but I got tired of being everybody’s bitch, and learned to spell things incorrectly and skip capitalization and punctuation on purpose whenever I would be expected to be too busy to do any better. In truth, I’m rarely too busy to write well.

    This whole discussion is almost irrelevant in 2015. I could probably check my email once a week without missing anything important. Everything that used to get done via email has migrated other places now.

  • Cruz5280

    Yet another home run, thanks for re-sending.

    Due to my penchant for pontificating, I will most likely re-state a few tidbits that help avoid some email tragedies:
    1- When writing important emails, include the email recipients address last
    2- Immediately attach a doc when writing an email rather than after you’ve written the text
    3- Use bcc very carefully. Although generally accepted as professional, bcc’ing is considered sneaky to many. I typically FWD messages to the appropriate recipients rather than bcc…..Just my .02 that nobody asked for.

    OK, my sermon is over.

    • bbroome62

      Nice work, Reverend.

  • Gudda

    Have suffered from the email disaster. Terrible. Don’t gossip kids.

  • bbroome62

    Idea for another article – I just realized that I replied to a comment made one year ago.

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