How Different Generations Respond to Emails Is Fascinating

And 15 ways you can sign off your emails to MAXIMIZE passive-aggressive chains.

Jul 31, 2023

I wouldn’t say that I am often on my best behavior even when I am in the office, exactly. Like many mildly ambitious weekend warriors, I embark on prolonged voyages to the bathroom stall and eat more granola bars from the kitchen cabinets than is socially acceptable. Maybe the more salient point here is that my “best behavior” is still pretty feral and scatterbrained, but the point I was endeavoring to make, and will hopefully have made by the time this sentence ends, is that I feel compelled to do my best to be extra courteous and properly perky whenever I email a co-worker. I think I do decently well at this; at the very least, I feel like I’ve mastered the delicate quota of appropriate exclamation points and how to keep my emails under 100 words. Which, I suppose, is to be celebrated and all that, but it is also exhausting for someone with my collection of deficits and defects to try to act not just normal but professional for several hours at a time. It is against the very essence of my being to go that long without making an inappropriate suicide joke or going off on a long, vague, ultra-headed stem-winder about whatever global issue is troubling my brain at that moment.

Anyways, I’d like to give special attention to celebrating each generation’s extremely different but similarly singular experience of maintaining email decorum. It is uniquely infuriating and fun to watch difficult and complex social navigation made to look breezy and like an unmitigated trainwreck.

How Boomers Email

Boomers will reply to your email by either calling you or stealthily moseying over to your desk to tap you on the shoulder at an inopportune time.

How Gen Xers Email

Gen Xers are the e e cummings of emailing.

their sentences begin with lowercase letters.

the subject line will be either one word or four words compressed intoasinglesyllable.

nothing ever has any punctuation

the content is peppered with one-sentence paragraphs.

and there are many hyphens that inexplicably lead to nowhere-

For whatever ungodly reason, their emails always… include… unnecessary... ellipses... in their messages...

Capping things off, their sign-off is even worse than “Sent from my iPhone,” because they want to attempt wit and subversion with something like “Sent from the magical little box from my pocket.” C’mon, Jared, we don’t need to do bits in the email signature.

How Millennials Email

Despite the clear technological illiteracy displayed by our elders, Millennials are somehow the most incompetent emailers because we are permanently racked with anxiety. If there is even one semi-important person CC’d, we will stare blankly into our MacBook, poring over the grammar, call in trusted confidants to also proofread, send a screenshot of it to our best friend to ask them, Is this ok or should I take away some of the exclamation points at the end of every sentence? Millennials love adding an exclamation point to appear casual and positive: “See you Tuesday!” … “Great point!” … “Just got home from therapy!” Of course, we will never send an email from our iPhone because we need to draft it as if we’re writing the State of the Union address.

We will reread and re-reread our email, bust out the thesaurus, internally debate whether the greeting is too informal, and have an existential deliberation over whether “Best” is an optimal email signature. When we finally muster the courage to click send, we will continue to read it even after we hear the nauseating ping that confirms its successful delivery. This is just to see how it looks from their perspective, but we inevitably cringe at the monstrosity we just sent. All of this needless second-guessing and fretting snowballs into an ongoing panic attack until we receive a response, which is likely the other person telling us that we forgot to attach the document—and that was the whole reason for the email!

How Gen Z Emails

There aren’t enough data points on Gen Z in the workforce to accurately analyze their email behavior, though I’m not entirely convinced they even know how to use email or even write fully developed sentences.

One of the scant few occasions they’ve sent an email is to ask their college professor for an extension on a paper. The only contents are a subject line that reads “Can I extension?” and an auto-filled signature with links to all their socials. Or, they will initiate an email exchange as if they are in mid-conversation with their friend, and they will only address you as “bestie” if they need a favor. Punctuation and capitalization are apparently optional.

Email sign-off alignment chart | Boing Boing

Let’s Spice Up Our Email Signatures

“Best” and “Sincerely” have been safe and steady sign-offs for most of the history of Corporate America, but the collective nervous breakdown that Covid wrought on our society has generated a Rennaissance in email decorum. I have seen “You’ll Never Take Me Alive” gain popularity on Twitter (X?), but as someone who already has to overcompensate for demented quirks, I opt for “Cheers.” Am I British? Am I drunk? It’s a mystery.

For the more daring and nihilistically charismatic, I have drafted some provocative sendoffs so I can vicariously live through you and all the HR-sanctioned chaos you will ignite amongst your colleagues in the ensuing passive-aggressive email chains.

“I hope this email finds you before I do,”
“Have the day you deserve,”
“Sent from my Nintendo DS,”
“I have lost control of the day,”
“Do not contact me with any questions or it will be considered harassment. Thanks!”
“We ride at dawn,”
“Trying my best,”
“Toodle loo bitch,”
“Seriously,”
“Yours in Christ,”
“Please hesitate to reach out,”
“With lukewarm regards,”
"Yours in malicious compliance,”
“Let’s NOT circle back,”
“Allegedly,”