When signing off an email there are only two apparent outcomes: getting it right, or getting it very, very, wrong.

Penning an important email is like the 21st century’s answer to jousting.

You’ve just gotta jump on your horse, run at the opposition, and hope for the best.

We’ve all been there: painstakingly tapping single key after single key, beads of sweat trickling down your face, catching your grimacing reflection in the computer screen. Writhing in your chair, wringing your hands, and desperately searching for a better phrase than ‘habitually unemployed’. Panicking because you’re taking too long (or not long enough). And then it dawns on you that the worst part is yet to come. The fundamental few words that separate the men from the boys, the women from the girls, and the Gen Y digital natives from, well, everyone else.

IT’S THE EMAIL SIGN OFF.

Warmest regards. Thanks. Best. Cheers. Yours truly. Best Wishes. All the best, Lots of love, Chat soon, Smiley face :), Kiss-hug-kiss-hug, xxx, Ciao. The options are endless but with only two apparent outcomes: getting it right, or getting it very, very, wrong.

Whether you are approaching a potential employer with your CV, signing off from a new colleague, or sending an ex-lover a large invoice containing every receipt pertaining to purchases for him during the duration of your short but tumultuous affair that YOU WANT TO BE PAID BACK FOR, GODDAMN IT – finding the right way to say ‘goodbye’ can be harder than you think.

To complicate the situation further, each and every industry has its own dust-covered spellbook containing the magical rules and codes of their specific email etiquette. Chucking a ‘xo’ or ‘:)’ onto the end of an email in the creative industries, for example, is totally kosher. Do that in the financial world however, and you will be assumed to be drunk or poaching for sex on the photocopying machine. Signing off ‘Yours sincerely’ in a corporate response on a Monday is showcasing the finest of manners, m’lady – but use it in an email to you boss on a Friday afternoon? Your attitude is becoming an issue around here, mate.

Listen: Robin Bailey in the case for stepping away from your emails, plus what is the Three Sentence Rule? (Post continues after audio.)

In turn, an unintentionally odd email sign off can achieve a myriad of strange and wonderful consequences. When she was but a middle-aged-babe in the online woods, my mother like to sign off her emails with ‘LOL, Mum.’ Although it seemed from afar that she was riding an alarmingly constant Prozac high of hysterical laughing-out-loud; she thankfully was still of sound mind…just a little confused on how to abbreviate ‘lots of love.’

A recent article in Bloomberg Business has tried to solve the age-old (well, two-decade old, at the very least) quandary of The Email Sign Off with the peculiar suggestion of, well, not signing off at all.

This from Bloomberg:

Best is safe, inoffensive. It’s also become completely and unnecessarily ubiquitous. That development is relatively recent: A University of Pennsylvania study from 2003 found that, out of hundreds of e-mailers, only 5 percent opted to close with best. It came in behind “thank you” and “regards.” But a quick search through your work account will quickly clear up two things: 1) No one says regards anymore; 2) everyone says best.

“So if not ‘best’, then what? Nothing. Don’t sign off at all. With the rise of Slack and other office chatting software, e-mail has begun functioning more like instant messaging anyway.”

UM, YOU GUYS, NO. That’s like watching an American sit-com where no one ever says goodbye, they just hang up the phone. This is not real life. You can’t just HANG UP ON SOMEBODY.

So with our options quickly diminishing, and the nugget of email anxiety firmly planted in your brain, let’s finish by walking through the standard responses you can choose from and why they are all terrible.

1. “Warmest regards” – What’s warm? Your regards? When I say this all I can imagine is a big, oozing, wet vat of something warm. Also, you sound like a primary school teacher on a 6th grade report card.

2. “Thanks” – Basically saying, “Oh girl you FOR REAL? Now you’ve made me mad. I’m quitting/ firing you/ going to spit in your coffee when you’re not looking.” The email equivalent of pursed lips.

3. “Best”– You can’t just sign off with a word, you arsehat. Best what? Best email ever written? Sadly for you, pal, you’ve spelt ‘ascertain’ wrong three times above. Best… of luck next time.

4. “Cheers” – Go home. You’re drunk.

5. “Ciao” – Unless you’re swarthy and Italian, this is a huge issue. You are the king of all sleazy sleazebags and I can smell the Brut from here.

6. “Yours truly” – Reserved exclusively for CV’s written by those 15 years old and under. And letters from irritating neighbours to your local council regarding the shared clothesline that you clearly own.

7. “Best Wishes” – This should only ever be employed by extended family on birthday cards and should always, always be accompanied by a $20 note.

8. “Lots of love” – I HAVE ASKED YOU ONCE ALREADY: Go home. You’re drunk.

9. “Chat soon” – Unlikely. Oh, unless you have received this from your accountant, a policeman, or your mother – in which case it means “you’re in deep shit.” Chat soon = I know where you live. RUN.

10. “Smiley face :) ” – Only ever used in two instances – firstly, if you’ve written a particularly sour email and need to leave it on a nice note without sacrificing any sourness. Or, on any email send post-4pm on a Friday. Because y’all wine draaaaankin.

11. Kiss-hug-kiss-hug/ xoxo / xxx – See you at in the photocopying room in ten.

As for me, I sign off with a single initial – ‘M’. Which renders me cold, impersonal, unimaginative, and brusque. Couldn’t have it put it better myself.

M.