When you realise you've accidentally hit 'reply all'. Photo / Thinkstock
Last week Google announced welcome news for anyone who has ever experienced the horror of sending an email to the wrong person - a new 'unsend' function that can cancel the message.
Here, six writers reveal the most embarrassing emails they wish they'd never sent:
WHAT'S THE MOST EMBARRASSING EMAIL YOU'VE EVER SENT? SEND US AN EMAIL
It was possibly the time my (now ex) friend Jane needed me most. She had recently been dumped by her long-term boyfriend and was devastated.
She was determined to win him back, however, by inviting him to her 40th birthday party and making herself irresistible. To do this she had a taffeta evening gown made specially.
But when it arrived and she showed me, I could see immediately that it was magenta, massive, and a major mistake.
"Do you like it?" she wanted to know, beaming and clearly not wanting to hear the truth. Who wants the truth when you've just spent £2,000 on a dress you can't return?
So, inevitably, I mumbled something about it being "lovely" and left.
Afterwards I sent a panic email to our mutual friend Stella saying we needed to make a last minute intervention: "What is she thinking?" I wrote. "She looks like a purple meringue. Her bum looks huge. He doesn't want her back anyway but especially not in that outfit. She just looks crazy. We have to do something."
But unfortunately I was replying to a previous email stream between the three of us and accidentally pressed 'Reply All'. Not that I immediately realised my mistake - not until five minutes later when Stella sent me an email with the catchline: "HAHA.OOPS".
I was then uninvited from the party - though I heard from Stella later that Jane wore the dress, and won the man back, too.
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Even now, four years later, I wince with embarrassment when I think of the email. I was organising a three-day golf trip for a bunch of mates from university and needed one more person to make up numbers, so invited an old school friend, Bill.
He didn't know the others, but I thought he'd fit in.
Bill cheerfully agreed so I sent round a group email, saying we now had a full complement and listing the 12 names.
Almost immediately one guy, Mark, dropped me a line asking who Bill was. I wrote back saying he was an old school friend, that I'd been best man at his wedding, but that I actually regretted inviting him because I'd subsequently been approached by another of the old university gang, for whom there was now no room.
Only I didn't just say that. For some witless reason I decided to be melodramatic and added that it had been a "ghastly mistake", for which I was "truly sorry", and that I would "take one for the team" by rooming with Bill myself.
Then, just to amuse myself further, I added that Bill had a few unpleasant personal habits, which I couldn't divulge. This was untrue, but it tickled me.
Finally, I pressed 'send' - realising perhaps a tenth of a second too late that I had ticked the dreaded 'Reply All' and that my email, intended only for Mark, was also whizzing through cyberspace to Bill.
After pacing the room for 20 mortified minutes, I phoned Bill. He didn't pick up, so I left a voicemail saying that he might have received an email sent accidentally, and that he must disregard it, as it was merely pandering to Mark's puerile sense of college camaraderie.
Mercifully, when I finally got through to Bill later he took my pathetic, grovelling apology like the exceptionally decent fellow, devoid of nasty personal habits, that he is.
As a children's author, I regularly visit schools to give a show called The Seven Secrets Of Storytelling and go round teaching the kids about writing. So I have lots of professional contacts in publishing and beyond, and I am always adding the email contacts of young teachers.
One night, when my wife was away for a few days, I emailed her asking how her dinner out had been. She replied, "Excruciating. For some reason all the women started competing about how much their husbands loved them."
I was touched, and missed her, so wrote back some words that I would never normally say: "I love you so much, and I simply cannot wait till you come home so we can be together."
As I am not very competent on email, I wrote this great love note out in Word then copied and pasted the text into the email and sent it to her.
At least, I tried to - the trouble is, I don't really understand computers and I'm easily distracted.
Somehow, I had pasted the text over a business message I'd prepared to all my contacts, telling them I had a new book out.
So instead, my wife received nothing while hundreds of other people received a message saying: "I love you and cannot wait till you come home". Those people included several young girls - I feel weak with horror just thinking about it.
To make matters worse, to hide the recipients on my business email I had blind copied all the names - so to anyone receiving the message it would have looked as if I was writing a special love message just for them.
Many years ago, when working in an office, I became close friends with Sarah, the company PA. We bonded over our mutual loathing of our boss who was lazy, surly, a nightmare to work with and a complete cheapskate - despite earning a comfortable six-figure salary.
She'd email me to bitch about how he never paid her back for all the coffees she bought him and how he would send her to Sainsbury's at 5pm when the sandwiches were marked down to half price.
But the thing we used to laugh about most was his appallingly dyed hair. Too tight to get it done professionally, he clearly did it himself at home with a sachet from Superdrug. He chose a ridiculous browny-red tone that would also stain all the skin around his forehead and ears.
One Monday, after he'd been dipping into the dye at the weekend, I couldn't resist sending Sarah a withering email: "A plum job," I wrote in the subject field, referring to the colour.
In the main body I wrote: "I see Chris has been colouring the Barnet again. He doesn't get any better at it does he? And why choose such a ridiculous colour - he looks like an ageing holiday camp singer."
As I soon as I hit 'send' I realised my mistake. Instead of emailing Sarah I had emailed my boss direct. He replied almost instantly with a brusque: "Not intended for me I don't think, Miss Connell."
There was no way of wriggling out of it, so all I could do was offer a lame "Whoops. Sorry about that" response.
He'd never been my number one fan and after my misfired email he despised me even more, taking delight in giving me my most hated tasks to perform.
I resigned three months later and have double checked every email I've ever sent since.
As part of a graduate training scheme in Aberdeen, I was sent to work in a motoring marketing department for a week.
My elderly boss was a Highlander who would dourly mutter about the caravanning supplement then not speak a word for the rest of the day, only sniffing to express disapproval.
I was desperate to impress him as he had to give me a good report so I could move on to the next stage of training.
Halfway through the first day - having painstakingly stuck up my thousandth picture of a caravan for a newsletter - I wrote an email to a friend: "I'm almost out of my mind with boredom. This is the most pointless thing I've ever done. I don't understand how anyone does this long-term without going mad. Yawn." Then promptly sent it to my boss accidentally.
In total horror - and seeing my chance gone for a glowing sign-off - I made a split-second decision to try to get away with it (ie. lie through my teeth) rather than confess and grovel.
I leaned over the desk, put on a winning smile and said: "Just to let you know, I've been asked to give you feedback on how well you're training me every day. I've just sent you today's - I was told I must be brutally honest so I have been. I do hope that's OK."
The poor man was very taken aback but believed me - and even stuttered out an apology about the "slow pace" of the work. I sent him glowing 'feedback' emails for the rest of the week and he signed me off without a hitch.
I still can't believe I got away with it - and I still feel guilty.
The email I wish I'd never sent was not just to my neighbour, who I'd got into a minor dispute with, but my entire street.
I was walking past the neighbour's house last year when I noticed a black bin bag she'd left at the front of her driveway had been torn open by a fox, resulting in food waste being strewn all over the street.
I bagged it all up then deposited the bag on her doorstep, along with a note, which I pinned to her door, reminding her to place any food waste in the hard green containers that we've been given for that purpose by the council.
A few days later I received an email from her, which she copied to everyone else on the street: "I have just returned from a trip abroad to find your very insulting note stuck to my front door," it began. "For your information, I have been a resident of this street for over 35 years and in all that long time I have never had a disagreement with my many neighbours. I certainly do not need a lecture from you on recycling or bin management."
The correct response from me then would have been to go round to her house with a bottle of wine and deliver a grovelling apology.
Instead, I replied to her email, copying in all the same people, saying that I had tried to be polite and underlining the importance of keeping rubbish off the street as it attracts "vermin, which can pose a threat to human health".
I now realise my response was pompous and patronising, and if I had the opportunity to take it back I would. My neighbour and I have not spoken since.
- Daily Mail
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